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$500

8 BR / 6 BA / Sleeps 16

Maryland Eastern Shore Waterfront Estate - Easton vacation rentals
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$500

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Maryland Eastern Shore Waterfront Estate

Trappe villa – 12.4 mi away
8 BR / 6 BA / Sleeps 16 | Quick view

Details

Martins Point is a late 18th Century house and cottages on Maryland's historic Eastern Shore where the Underground Railroad once passed through the property. It is located on a secluded finger of land, surrounded by water on three sides, a place to unwind, immerse yourself in the natural beauty of the Chesapeake Bay …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - elevator access

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$164

3 BR / 2 BA / Sleeps 8

Fun DC/Annaoplis Chesapeake Waterfront Cottge - Easton vacation rentals
1 / 49

$164

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Fun DC/Annaoplis Chesapeake Waterfront Cottge

Deale house – 19.0 mi away
3 BR / 2 BA / Sleeps 8 | Quick view

Details

This 3 bedroom/2 bath cottage is just the spot for a get-away with other couples or your entire family! Nestled on 2 country-like acres in a surprisingly convenient corner of the Chesapeake Bay, this unique area is just over 20 minutes south of Annapolis and 45 minutes from Wash DC, Alexandria VA, or Baltimore. …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Washing Machine
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$375

3 BR / 4 BA / Sleeps 6

Charming Artists Home in Eastport/Annapolis - Easton vacation rentals
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$375

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Charming Artists Home in Eastport/Annapolis

Annapolis house – 19.3 mi away
3 BR / 4 BA / Sleeps 6 | Quick view

Details

HOUSE This fully renovated, circa 1890 ,Victorian house is located in the middle of the Eastport peninsula . The house is within walking distance, or a three minute taxi ride, to downtown historic Annapolis and the US Naval Academy, as well as shopping, several marinas, theater, numerous restaurants, bars, coffee …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children - ask

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$175

3 BR / 2 BA / Sleeps 6

3 Reviews

$175

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Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge

Tilghman cottage – 10.8 mi away
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

Enjoy the beauty and tranquility of Tilghman Island from this bright and comfortable 3 bedroom, 2 bathroom cottage known for many years as the vacation rental 'The Roost.' Available for both short and long-term rentals, the cottage is located on a quiet residential street across from a marina on Knapps Narrows. …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(3)

Relaxing weekend stay

Left on Mar 08, 2014 for a stay in March 2014

My husband and I spent a weekend at the Roost on Tilghman Island and it was so relaxing. We were really able to unplug and I slept better in their loft bedroom than I had in my own bed in weeks. The cottage was really sweet- it looks small on the outside but it's actually very spacious and I love how it was decorated. Everything was spotless and in good working order. We enjoyed the sun room/…

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$90

3 BR / 3 BA / Sleeps 6

2 Reviews

$90

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Waterfront Vacation Room Rentals

Trappe house – 16.9 mi away
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

Beautiful, serene waterfront home on the Chesapeake Bay. One hour from the Atlantic Ocean (Ocean City, Assateague Island) and Annapolis, One and a half hours from Washington DC and Baltimore. Many nearby places worth visiting, including picturesque St. Michaels and the Blackwater Wildlife Refuge (home of the bald …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Dimitri is an unbelievable host! There wasn't any stone he left unturnrned in order to provide us w

Left on Aug 14, 2014 for a stay in August 2014

Our stay was incredible!! The house was spotless and offered every convience one could want! If it wasn't there all you had to do was ask for it and he provided it or informed you where you could get it!

Our stay was really disjointed by this weeks Bad Storm! But the Chesepeake Bay side home weathered it relentlessly. Only to have a beautiful week to look forward to!

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$400

2 BR / 2 BA / Sleeps 10

Unique Accommodation for 10 in Annapolis, MD - Easton vacation rentals
1 / 23

$400

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Unique Accommodation for 10 in Annapolis, MD

Annapolis cottage – 19.3 mi away
2 BR / 2 BA / Sleeps 10 | Quick view

Details

************* NEW LISTING - AVAILABLE NOW ************ SAILBOAT SHOW 2014 - $5000.00/wk POWER BOAT SHOW 2014 - $5000.00/wk CHRISTMAS 2014 - $5000.00/wk COMMISSIONING WEEK 2015 - $5000.00/wk Eastport cottage sleeps 10 - 2 bedrooms with sleeping loft - 1 full and 1 half bath - 2 premium queen beds - 1 pull-out …
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$450

3 BR / 3 BA / Sleeps 10

5 Reviews

$450

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Beautiful St. Michaels House Steps from Water and Town

Saint Michaels house – 3.4 mi away
3 BR / 3 BA / Sleeps 10 | Quick view
Excellent5 Reviews

Details

Reviews

(5)

Beautiful in town location! Just steps to shops, restaurants, winery, brewery, community pool, museums, boat ramp, and waterfront. This home has been renovated with amenities that will ensure a great time in St. Michaels. Home has three bedrooms; main floor master with a king and full bath, second floor has one …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(5)

Great Location, Great House, Great Time

Left on Jul 13, 2014 for a stay in July 2014

This house was perfect for a large family and very convenient for walking to sites in town. The house had a well equipped kitchen, nice backyard and barbecue grill. Within walking distance to local parks and public pool. We had nice holiday!

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$280

4 BR / 2 BA / Sleeps 8

2 Reviews

$280

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Peaceful, Waterfront Home w/Pier on Kent Island

Chester house – 11.5 mi away
4 BR / 2 BA / Sleeps 8 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

Waterfront Rancher on 3 acres, centrally located between Washington DC, St. Michaels, Annapolis, and Baltimore. 4 Bed/2 Bath home with central air sleeps 8. This home has been in our family for over 50 years and is a special place. Over the years there have been many updates to the home. The location is serene on a 3 …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

Unbelievable value

Left on Nov 04, 2010 for a stay in May 2010

We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we…

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$209

2 BR / 1 BA / Sleeps 6

1 / 11

$209

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Love Point Bay Vacation Home

Stevensville condo – 15.3 mi away
2 BR / 1 BA / Sleeps 6 | Quick view

Details

Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave your worries behind …
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

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    $450

    4 BR / 3 BA / Sleeps 10

    1 / 12

    $450

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    Chesapeake Bay Luxury Vacation Home, 5 Star

    Grasonville house – 11.3 mi away
    4 BR / 3 BA / Sleeps 10 | Quick view

    Details

    Welcome to Baydreams vacation home, a unique waterfront vacation home situated near the Kent Narrows in Queen Anne's County, on the Eastern Shore of Maryland. Book the comfort and convenience of a 4 bedroom 3 bath home offering a unique lodging to the discriminating traveler that other accommodations do not. For large…
    • Waterfront
    • Hot Tub/Jacuzzi
    • Internet Access
    • Fireplace
    • Washing Machine
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $450

    3 BR / 2 BA / Sleeps 8

    1 / 7

    $450

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    Charming Townhouse - Steps to City Dock and USNA

    Annapolis house – 19.9 mi away
    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    Shellback house is a three bedroom, one and 1/2 bath historic townhouse in the heart of Downtown Annapolis with a private garden. The house has views of Ego Alley (Annapolis Waterfront) from the front stoop and the master bedroom. BOOK NOW FOR 2015 LEGISLATIVE SESSION AT STIPEND RATES! Please note - the standard …
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $375

    4 BR / 3 BA / Sleeps 10

    1 Reviews

    $375

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    Sandy Pines: Enjoy Harris Creek w/Pool and Boats

    Saint Michaels house – 8.4 mi away
    4 BR / 3 BA / Sleeps 10 | Quick view
    Excellent1 Reviews

    Details

    Reviews

    (1)

    Sandy Pines, with its own waterfront, dock, and swimming pool, offers a peaceful retreat within the quiet natural beauty of the Chesapeake Bay region. The very private home, sited on broad Harris Creek, enjoys stunning sunset views across the Chesapeake tributary, and is fully-equipped and furnished for a comfortable …
    • Waterfront
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Internet Access
    • Fireplace
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Perfect weekend getaway!

    Left on Jan 10, 2014 for a stay in December 2013

    My family recently spent a memorable weekend in December at Sandy Pines. We comfortably shared the house with a group of friends -- three other couples and their young children. The house has a lovely home-away-from-home feel. We especially enjoyed the wood-burning fireplace in the evenings.
    Sandy Pines is perfectly situated -- a short drive from St. Michaels, and on a tranquil spot by the Bay…

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    $257

    4 BR / 3 BA / Sleeps 10

    1 / 17

    $257

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    KI Golf House:A Par for the Course&Mile from Beach

    Kent Island house – 11.5 mi away
    4 BR / 3 BA / Sleeps 10 | Quick view

    Details

    LOCATION…STAYCATION…GOLFCATION…right on Kent Island! KI Golf House: A Par for the Course Less than a mile to Dirty Dave's a gorgeous little beach and tiki bar. A short walk to the Chesapeake Bay. Call/email Donna and book it today! KI Golf House offers 4 Bedrooms, 2 ½ Baths, an open Kitchen Dining area…
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $575

    4 BR / 4 BA / Sleeps 14

    1 / 23

    $575

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    Chesapeake Bay Spectacular

    Stevensville house – 10.8 mi away
    4 BR / 4 BA / Sleeps 14 | Quick view

    Details

    Beautiful 4 Bedroom, 4 Bath Quiet Waterfront Property, 3 queen bedrooms, 1 twin beds, 4 baths, two stories, fantastic master bedroom with mater bath complete with Roman soaking tub. Deck off of the master bedroom. Formal living room, Family room, Glass Sunroom, eat in kitchen, this spacious comes complete with …
    • Waterfront
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Washing Machine
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $759

    6 BR / 6 BA / Sleeps 12

    1 / 38

    $759

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    BayCottage Waterfront Vacation Retreat St.Michaels

    Saint Michaels villa – 2.7 mi away
    6 BR / 6 BA / Sleeps 12 | Quick view

    Details

    Walk to the attractions of St. Michaels, MD, yet private and quiet on a point of land with 500' shoreline, Bay Cottage is your home on the Chesapeake Bay with a relaxing waterside pol, private harbor and pier, organic culinary gardens, fruit farm, wellness studio, and warm hospitalities. There are 6 bedrooms, 5.5 …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

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    $449

    7 BR / 5 BA / Sleeps 18

    11 Reviews

    $449

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    Waterfront Chespeake Bay Retreat

    Cambridge house – 15.4 mi away
    7 BR / 5 BA / Sleeps 18 | Quick view
    Excellent11 Reviews

    Details

    Reviews

    (11)

    New premier waterfront vacation home - 6bed / 5bath home w/ beach & private pool. All of this on over 3 acres and +- 400 feet of stunning waterfront Near Cambridge Maryland, also Easton, St. Michaels and Oxford. The den also serves as an additional bdrm with full bath making it 7bdrms. Ideal for large family …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Fireplace
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (11)

    Wondeful home - Great for Fishing!

    Left on May 04, 2009 for a stay in April 2009

    We had an amazing week at this gorgeous house. The house is brand new and immaculate. Everything in it is brand new!! It truly felt like home. The owners are amazing - it was a warmer week than expected and they went out of their way to open the pool for us. They also gave a lot of great recommendations on places to eat. We took out the boat and the kids had a great time fishing and …

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    $250

    3 BR / 4 BA / Sleeps 8

    1 Reviews

    $250

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    ENDLESS SUNSETS - The perfect getaway!

    Claiborne house – 5.5 mi away
    3 BR / 4 BA / Sleeps 8 | Quick view
    Excellent1 Reviews

    Details

    Reviews

    (1)

    Beautiful like new waterfront home on the Chesapeake Bay, 5 minute drive to Historic St. Michaels. Minutes to many quaint watermen villages. Shared waterside pool, beach, kayaks, small boat, childrens playset. The property was designed to take advantage of the incredible views of the Chesapeake Bay. Every bedroom …
    • Waterfront
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Hard to find and worth the effort

    Left on Oct 10, 2014 for a stay in September 2014

    Very new, very clean, very spacious, very comfortable. The family thoroughly enjoyed our stay here with plenty of room to spread out, a huge kitchen, meals on the deck and bathrooms galore. The only nitpick I have is the wifi seemed to fade in and out kicking us off regularly.

    But with such a great view and wonderful sunsets - you won't want to be on wifi anyway.

    Be sure to get good …

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    $190

    3 BR / 1 BA / Sleeps 5

    1 / 41

    $190

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    "The Cottage" Cambridge Chesapeake Waterfront Home

    Cambridge cottage – 16.7 mi away
    3 BR / 1 BA / Sleeps 5 | Quick view

    Details

    "The Cottage" at Heron Cove is a cozy home situated on a scenic peninsula with water views from every window. Awake each morning to watch the sun glisten off the gentle waters. Explore ten acres of land and 1000 feet of shoreline. Relax on the wrap around screened in porch or soak in the 450 gallon hot tub. Fish and …
    • Waterfront
    • Hot Tub/Jacuzzi
    • A/C or climate control
    • Central heating
    • Deck
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $1,200

    5 BR / 4 BA / Sleeps 18

    2 Reviews

    $1,200

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    Yr Round Waterfront Home w/ Dock & Pool - Slps 18

    Cambridge house – 18.0 mi away
    5 BR / 4 BA / Sleeps 18 | Quick view
    Excellent2 Reviews

    Details

    Reviews

    (2)

    Swan Cove awaits your family vacation or group! It's also an ideal place for a most memorable wedding. This incredible, newly redesigned waterfront home with a private dock offers spectacular views with a large swimming pool, 4 kayaks, outdoor firepit (firewood is furnished), playground and a large outdoor grill. The …
    • Waterfront
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Internet Access
    • Fireplace
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Dream vacation

    Left on Oct 18, 2012 for a stay in August 2012

    We spent a week a Swan cove. the entire Family loved the house. Very spacious, clean and the kids had a blast in the pool. Great setting with the private dock, fire pit, playground just an amazing home.
    We already reserved for next year!!!

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    $250

    3 BR / 2 BA / Sleeps 6

    1 Reviews

    $250

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    Unique, Affordable Nature-Oriented Getaway Home

    Cambridge house – 16.1 mi away
    3 BR / 2 BA / Sleeps 6 | Quick view
    Average1 Reviews

    Details

    Reviews

    (1)

    Charming, historic home in the Neck District, Maryland's most beautiful, unspoiled area. This adorable east-facing 100-year-old home sits on a generous lot (over an acre) with forever waterviews, mature shade trees, flowering perennials, roses, large fenced vegetable garden, breezy patio, wide covered front porch and …
      • Pet friendly
      • Smoking allowed - ask
      • Suitable for the elderly - ask

      Details

      Reviews

      (1)

      Nice house but it is not on the water

      Left on Oct 26, 2012 for a stay in July 2012

      This is a lovely older house with lots of room for families. We are very grateful that she accepts dogs and even better that the house is so clean you can't tell that dogs have stayed there. The electronics are a bit old but useable and there is no wifi. There are bikes available for use and the area would be great for bike riding but in July when we were there it was over 100 every day and …

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      $375

      4 BR / 4 BA / Sleeps 10

      1 / 37

      $375

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      Luxury vacation condominum with private beach

      Chester house – 11.5 mi away
      4 BR / 4 BA / Sleeps 10 | Quick view

      Details

      Swan Cove Condominiums at Kent Narrows(#49064) with private beach and views of the Chesapeake bay! - Brand new luxury condominium with 3000 sq ft, 4 bedrooms, 3 ½ bathrooms, one large family room with open kitchen, one large sunny living room and dinning area. There are 2 king size bed, 2 queen size bed for the 4…
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Fireplace
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $500

      6 BR / 3 BA / Sleeps 18

      6 Reviews

      $500

      Inquire

      Chesapeake Bay Waterfront, Private Dock, Beach

      Cambridge house – 19.2 mi away
      6 BR / 3 BA / Sleeps 18 | Quick view
      Excellent6 Reviews

      Details

      Reviews

      (6)

      The Swan's Nest in Cambridge, Maryland, has all that the Chesapeake Bay has to offer: sun, sand, fishing, crabbing, a par 3 golf course on site and so much more. The spacious and lovingly restored farmhouse can accommodate 18 guests. The kitchen is fully equipped and a barbeque pit is just outside on the patio. …
      • Waterfront
      • Ocean or water views
      • Shared outdoor pool (unheated)
      • Internet Access
      • Fireplace
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (6)

      Fantastic Bay Experience!

      Left on Jul 16, 2012 for a stay in July 2012

      My extended family (12 plus part week guests) just got back from a week at Swan's Nest. Hap was a fantastic host and tried really hard to ensure we had what we needed for the needs and interests of our group. I can't say enough about his personal involvement and patience in answering our questions.

      It was a fantastic experience - we went crabbing - a lot - we brought supplies to run a trot …

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      $250

      3 BR / 2 BA / Sleeps 6

      1 Reviews

      $250

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      Charming Vintage Cottage/secluded Yard/Walk. WIFI

      Annapolis cottage – 19.7 mi away
      3 BR / 2 BA / Sleeps 6 | Quick view
      Excellent1 Reviews

      Details

      Reviews

      (1)

      History, waterfront, rooftop restaurants, wine bars, sailing, kayaking and more. We have everything here in Annapolis - USNA, sailing, culture, world-class restaurants & a vibrant, walkable capital city! Here in Upper Eastport, on a cul de sac, we are a short walk to the Historic Harbor & 3 blocks from Spa …
      • Wireless Internet
      • Fireplace
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (1)

      Great place. My dog loved the yard. I loved the Porch

      Left on Jul 15, 2014 for a stay in December 2013

      If you want a cozy place to relax this is the place. Yard was perfect for my dog to run around and I did not have to worry it was all fenced in. Love to grill so I was able to grill a couple a steaks and have a semi barbeque (little cold so the porch was perfect) by eating and entertaining on the Porch.

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      $449

      6 BR / 5 BA / Sleeps 16

      9 Reviews

      $449

      Inquire

      Stunning, Newer Chesapeake Waterfront Rental

      Cambridge house – 19.8 mi away
      6 BR / 5 BA / Sleeps 16 | Quick view
      Excellent9 Reviews

      Details

      Reviews

      (9)

      Fabulous, recently-built premier vacation home on 500 feet of Chesapeake waterfront. A gorgeous home; beach, dock, private pool, boats, bikes, porches & mile-wide view With 6 acres of property, wide water & sandy beaches, this private luxury vacation rental is minutes from Cambridge, Easton, Oxford & St. …
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Sauna
      • Internet Access
      • Suitable for children
      • Suitable for the elderly - ask

      Details

      Reviews

      (9)

      GREAT Vacation!

      Left on May 05, 2009 for a stay in August 2008

      We really had a GREAT stay. The house is much more than we expected; it's very well done and comfortable (the owner was nice as well). The water views are amazing and the grounds perfect. We swam, fished, crabbed, biked and boated - had a great time off property as well. This was a TOP notch vacation.- thanks!

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      $250

      2 BR / 2 BA / Sleeps 4

      1 / 8

      $250

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      Waterfront Boat Vacation Rental

      Davidsonville houseboat – 12.6 mi away
      2 BR / 2 BA / Sleeps 4 | Quick view

      Details

      2 bedroom, 2 bath with living salon, kitchen, and an aft deck
      • Waterfront
      • Shared outdoor pool (unheated)
      • Hot Tub/Jacuzzi
      • Sauna
      • Internet Access
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for the elderly - ask

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      $190

      2 BR / 2 BA / Sleeps 4

      1 Reviews

      $190

      Inquire

      Premier Cottage in St. Michaels- In Town Location!

      Saint Michaels house – 3.2 mi away
      2 BR / 2 BA / Sleeps 4 | Quick view
      Excellent1 Reviews

      Details

      Reviews

      (1)

      The historic and recently restored Thomas Blades House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, parks, restaurants, town pool, library, churches and shops in St. Michaels. The house was built around 1850 by Thomas Blades, a young sailor. The first floor of the…
      • Ocean or water views
      • Internet Access
      • Fireplace
      • Washing Machine
      • Clothes Dryer
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (1)

      I will never go back to the Jersey Shore Again!!!

      Left on Aug 18, 2014 for a stay in August 2014

      Location location location!

      Walk to perhaps the cutest town ever! Friendly people ,dog loving community, sail boats, restaurants and such a lovely little town.. Perfection found!

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      $200

      4 BR / 2 BA / Sleeps 8

      1 / 18

      $200

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      Snug Harbor USNA Cottage in Eastport Annapolis

      Annapolis house – 19.8 mi away
      4 BR / 2 BA / Sleeps 8 | Quick view

      Details

      The perfect retreat for a family visiting Annapolis on vacation or for visiting your Johnny or Midshipman at the Naval Academy. This house is modestly priced yet has all the amenities and comfort of a home and the ability to eat in and cook your meals in our huge fully equipped kitchen or barbecue out back on the …
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • A/C or climate control
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible

      PreviousNext property

      $180

      2 BR / 2 BA / Sleeps 5

      12 Reviews

      $180

      Inquire

      Location Location! St Michaels-- In Town Cottage!

      Saint Michaels house – 3.2 mi away
      2 BR / 2 BA / Sleeps 5 | Quick view
      Excellent12 Reviews

      Details

      Reviews

      (12)

      The recently restored historic Washington Melson House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, town pool, parks, restaurants, library, churches and shops in St. Michaels. The house was built around 1840 by Washington Melson, a sailor, believed to be one of two …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Fireplace
      • Washing Machine
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible - ask

      Details

      Reviews

      (12)

      Crabtastic Great Escape

      Left on Aug 26, 2011 for a stay in August 2011

      This cottage is the perfect great escape. Conveniently located in the middle of quaint St Michael's close to the harbor, restaurants, and shops. The property is clean and well-maintained with beautiful landscaping. The building has been lovingly restored keeping to the historical accuracy, yet well placed modern conveniences make the stay even more enjoyable.

      I have visited this cottage several…

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      $450

      3 BR / 3 BA / Sleeps 8

      1 / 18

      $450

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      Historic Waterfront Property with Wi-Fi and Dock

      Saint Michaels house – 4.2 mi away
      3 BR / 3 BA / Sleeps 8 | Quick view

      Details

      Cranford on the Miles is a waterfront home located on 3+ acres, in St. Michaels. Fully renovated, with Wi-Fi, there is a Master Bedroom with king bed, sitting room, and private balcony; Second Bedroom with a double bed; Third Bedroom with both a double and twin bed; and a Den with a trundle bed with 2 twins beds and a…
      • Waterfront
      • Wireless Internet
      • Fireplace
      • Washing Machine
      • Clothes Dryer
      • Pet friendly - ask
      • Suitable for children

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      $250

      4 BR / 3 BA / Sleeps 8

      1 / 17

      $250

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      Chez Cinquai

      Tilghman house – 10.7 mi away
      4 BR / 3 BA / Sleeps 8 | Quick view

      Details

      Located in the heart of the classic waterman's village of Tilghman Island, this gorgeous Knapps Narrows waterfront home comes complete with a boat slip! Watch the boats stream by, fish, crab or just relax in this 2700 sq ft home. This stunning vacation home boasts an open floor-plan, gourmet kitchen, custom wood …
      • Waterfront
      • Ocean or water views
      • Wireless Internet
      • Washing Machine
      • Clothes Dryer
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly - ask

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      $350

      7 BR / 4 BA / Sleeps 11

      2 Reviews

      $350

      Inquire

      Large Historic Home On Harbor in St. Michaels

      Saint Michaels house – 3.2 mi away
      7 BR / 4 BA / Sleeps 11 | Quick view
      Excellent2 Reviews

      Details

      Reviews

      (2)

      The historic Thomas Harrison House is located on the harbor in the center of the town of St. Michaels. This Eastern Shore/Chesapeake Bay vacation rental has magnificent water VIEWS and can accomodate up to 12 people. The house is a short walk from all the museums, parks, restaurants, churches, and shops in St. …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Fireplace
      • Washing Machine
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly - ask

      Details

      Reviews

      (2)

      This was the perfect home for a week of wedding planning and family relaxation time.

      Left on Jul 23, 2014 for a stay in June 2014

      Our daughter was married at the Tidewater Inn in Easton. We rented this lovely, large home the week before the wedding to have a place for the bride to relax while we spent time together finalizing wedding plans. The stay at the Harrison Home added so many memories to the already fond memories of a wedding. We cooked together with all the amenities in the kitchen. The home was so large we could …

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      $500

      4 BR / 4 BA / Sleeps 8

      1 / 13

      $500

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      10 Minute Walk to Dwtn or Use Free Shuttle!

      Annapolis house – 19.6 mi away
      4 BR / 4 BA / Sleeps 8 | Quick view

      Details

      NOTE: Please call me if you want to book my property. There have been security problems on all vacation rental sites. If anyone should ask you to wire funds please call me at the number listed on this site. Beautiful upgraded home in Eastport is perfectly located in small Cul De Sac neighborhoods and features …
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • A/C or climate control
      • Deck
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $1,500

      0 BR / 4 BA / Sleeps 6

      1 / 7

      $1,500

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      Eastern Shore Vacation Rental

      Oxford house – 8.8 mi away
      0 BR / 4 BA / Sleeps 6 | Quick view

      Details

      Secluded, tranquil home located on the water, between Easton and Oxford, Maryland. Includes five bedrooms, four bathrooms, fully equipped kitchen, sun porch, swimming pool and tennis courts. Grounds include private driveway, miles of walking paths, and dock with two kayaks.
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Fireplace
      • Housekeeping Optional
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $375

      2 BR / 1 BA / Sleeps 6

      1 Reviews

      $375

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      Cottage 2 at Grandview Pleasure Point

      Bozman house – 8.5 mi away
      2 BR / 1 BA / Sleeps 6 | Quick view
      Excellent1 Reviews

      Details

      Reviews

      (1)

      The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, valences, sofas, wing and lounge chairs and collectibles. All the cottages are fully furnished including solaria porch, gas fireplaces, air …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Fireplace
      • Outdoor Dining Area
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (1)

      Wonderful!

      Left on Sep 30, 2013 for a stay in September 2013

      Our family has been vacationing at Grandview for over 20 years. I think that says it all. Beautiful location, gorgeous sunsets, peaceful and quite. Serene. Plenty of crabbing, swimming, fishing and just plan relaxing. The cottages are nicely furnished, cozy, clean and well-stocked kitchen. Plenty to do in the area-close to St. Michaels, hiking, cycling, nice restaurants. We love it here.

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      $1,100

      7 BR / 6 BA / Sleeps 28

      5 Reviews

      $1,100

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      Yr Round Estate on Bay / Family Reunions Sleeps 28

      Cambridge villa – 18.8 mi away
      7 BR / 6 BA / Sleeps 28 | Quick view
      Excellent5 Reviews

      Details

      Reviews

      (5)

      Experience the lavish surroundings of Captain's Quarters. Whether your pleasure is sailing, fishing, water sports, relaxing by the pool and jacuzzi or nestling up on the veranda with a good book, Captain's Quarter's provides luxury around every corner. This unrivaled waterfront estate accommodates up to 28 people and …
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Fireplace
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (5)

      Great hospitality...

      Left on Apr 24, 2012 for a stay in April 2012

      The house is well decorated and spacious, fantastic for family gatherings. We had a great experience that will be remembered for the rest of our lives.

      This property had all you needed for a great family vacation, but above all, the owner is a master of hospitality - he was very accommodating to every request we had.

      I hope to go back to this house for another week soon.

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      $280

      3 BR / 3 BA / Sleeps 6

      1 / 9

      $280

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      RESTORED WATERFRONT COTTAGE

      Saint Michaels cottage – 3.5 mi away
      3 BR / 3 BA / Sleeps 6 | Quick view

      Details

      You can tell right away, from the warm sage green exterior and the peaceful creekside setting, that this charming vacation cottage promises a fun, relaxing getaway. With a 180 degree expanse of spectacular Oak Creek waterfront, the River House at Royal Oak is the pefect choice for year 'round vacationing. Our …
      • Waterfront
      • Internet Access
      • Fireplace
      • Washing Machine
      • Clothes Dryer
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $350

      3 BR / 2 BA / Sleeps 12

      2 Reviews

      $350

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      Love Point Waterfront

      Kent Island house – 16.7 mi away
      3 BR / 2 BA / Sleeps 12 | Quick view
      Excellent2 Reviews

      Details

      Reviews

      (2)

      Located on the Eastern shore of Maryland, Kent Island is a small area 13 miles long and 5 miles wide. The Bay Bridge spans the Cheasapeake bay from the Western shore to Kent Island. We are 4.5 miles north of the bridge in a charming old waterfront community called Love Point! Love Point is quiet area of single …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Fireplace
      • Housekeeping Optional
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible

      Details

      Reviews

      (2)

      Home away from Home , We feel the weight of the world disappear when we walk through the door.

      Left on Apr 17, 2015 for a stay in April 2015

      Paula's Bay House is home away from home. like visiting the vacation house your family has had for years. You have a wall of windows view of the water. We spend hours just watching the birds and the waves. At night we stoke up the fire and gaze at the flickering flames and just be in the moment of quiet and peaceful relaxation. This house is warm and eclectic , has all the modern conveniences…

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      $665

      4 BR / 3 BA / Sleeps 13

      8 Reviews

      $665

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      Grandview Mainhouse

      Bozman house – 8.5 mi away
      4 BR / 3 BA / Sleeps 13 | Quick view
      Excellent8 Reviews

      Details

      Reviews

      (8)

      Beautiful NEW kitchen... Featuring two interior eating/serving areas, custom french windows that open to a sitting area on the porch, 4 bedrooms & Enclosed Sleeping Porch (2 queens, 1 double, daybed w/trundle, 5 twins) 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large living room, …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (8)

      relaxing

      Left on Jun 24, 2011 for a stay in September 2010

      A secret hideaway! We had never been to St. Michael's and even though this is out of town we like privacy. We stayed in one of the smaller units and it was perfect. Clean and updated with beautiful finishes. Would have loved to have a motor on the boat though!

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      $800

      3 BR / 3 BA / Sleeps 10

      1 Reviews

      $800

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      Beautifully water front Contemporary Home in Bay Ridge, Annapolis

      Annapolis house – 17.3 mi away
      3 BR / 3 BA / Sleeps 10 | Quick view
      Excellent1 Reviews

      Details

      Reviews

      (1)

      Bright, open, waterfront contemporary located on a landscaped property with magnificent views of Lake Ogleton! Pier (4'MLW) for your boat, crabbing, fishing and swimming. Bay Ridge Subdivison has great views, sandy beaches, streets for jogging, nature walks, and just great places to chill. Once you see the view …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Fireplace
      • Housekeeping Optional
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (1)

      Wonderful Family House!

      Left on Oct 17, 2013 for a stay in August 2013

      We were fortunate to stay in this lovely home over Plebe Parent Weekend. It was perfect for our family of 6. There was plenty of room to spread out or come together for family time. The large dining table made us feel right at home. The bedding was fresh with new linens and towels in all the rooms. We enjoyed the lovely water views and great location. The Bay Ridge house is a short ride to the …

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      $250

      2 BR / 1 BA / Sleeps 4

      1 / 12

      $250

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      2 Bedroom Unique Private Waterfront Escape

      Easton condo
      2 BR / 1 BA / Sleeps 4 | Quick view

      Details

      Exclusive 2 bedroom upstairs waterfront apartment with private entrance located 20 minutes from historic Easton and St. Michaels and 30 minutes from Oxford. Enjoy the sunrise each morning on your own private deck overlooking one of the most peaceful and unique surroundings the Eastern Shore has to offer! The …
      • Waterfront
      • Ocean or water views
      • Wireless Internet
      • Washing Machine
      • Clothes Dryer

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      $350

      3 BR / 7 BA / Sleeps 10

      1 Reviews

      $350

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      WATERFRONT SUISSE CHALET

      Annapolis house – 19.7 mi away
      3 BR / 7 BA / Sleeps 10 | Quick view
      Excellent1 Reviews

      Details

      Reviews

      (1)

      This spacious, airy and relaxing 3 bedroom Suisse Chalet sits on Mill Creek just off of the Chesapeake Bay and the Severn River. Located on Mulberry Hill Road, Annapolis, Maryland this beautiful and spacious Suisse Chalet is located 5 minutes from the United States Naval Academy, the community of West Annapolis and …
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Wireless Internet
      • Fireplace
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (1)

      Great Stay, very nice location and clean home

      Left on Apr 09, 2015 for a stay in April 2015

      The home was located at a very continent location just 5-10mins drive to Naval academy and Annapolis downtown. The home was clean and have all the amenities. The water views from the house and easy access to the waterfront right behind the home make the stay even more memorable. I will recommend this place.

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      $295

      4 BR / 3 BA / Sleeps 8

      1 / 6

      $295

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      Downtown Annapolis !

      Annapolis house – 19.1 mi away
      4 BR / 3 BA / Sleeps 8 | Quick view

      Details

      Our home is located in the Eastport section of Annapolis and just a short walk to Main street, the Historic District and the Naval Academy. We have a large back yard that's great for entertaining, plenty of off street parking and we're just across the street from the best view of the Chesapeake Bay Annapolis has to …
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible - ask

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      $595

      5 BR / 3 BA / Sleeps 20

      1 / 26

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      Annapolis Crows Nest Cottage: Chesapeake Bay View

      Annapolis villa – 16.7 mi away
      5 BR / 3 BA / Sleeps 20 | Quick view

      Details

      Comfort & Style: Enjoy stunning Chesapeake Bay Views, Beach, Pier, Boat Slips, Park, Water Access, Fire Pit, Patio Heater and more! Charming cottage & detached studio/game room (both upgraded in 2013) offer gourmet kitchen with new stainless steel appliances, a second full kitchen in garden level, spa inspired …
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Fireplace
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly

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      2 BR / 1 BA / Sleeps 4

      1 / 16

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      204 Shipping Creek Dr.

      Stevensville house – 11.3 mi away
      2 BR / 1 BA / Sleeps 4 | Quick view

      Details

      This lovely cottage hideaway, inlaw suite is in the tree tops above a three car extended garage. Lovingly appointed with twin tester beds in one bedroom and a queen in the master. It has many lovely antique pieces,inhereted from relatives. An in ground poolwelcomes you and the warmseasons. Situated on a tip of Kent …
      • Shared outdoor pool (unheated)
      • A/C or climate control
      • Parking
      • Grill
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      4 BR / 3 BA / Sleeps 10

      1 / 1

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      1010 Moss Haven Road

      Annapolis house – 20.0 mi away
      4 BR / 3 BA / Sleeps 10 | Quick view

      Details

      N/A
      • Fireplace
      • A/C or climate control
      • Balcony or terrace
      • Parking
      • Grill
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      3 BR / 3 BA / Sleeps 8

      1 / 23

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      2 Upshur Ave

      Annapolis house – 17.1 mi away
      3 BR / 3 BA / Sleeps 8 | Quick view

      Details

      N/A
      • Shared outdoor pool (unheated)
      • Fireplace
      • A/C or climate control
      • Parking
      • Grill
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      2 BR / 1 BA / Sleeps 6

      1 / 2

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      301 Burnside B102

      Annapolis house – 19.7 mi away
      2 BR / 1 BA / Sleeps 6 | Quick view

      Details

      N/A
      • Shared outdoor pool (unheated)
      • A/C or climate control
      • Balcony or terrace
      • Parking
      • Grill
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      3 BR / 4 BA / Sleeps 8

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      2203 Mulberry Hill

      Annapolis house – 19.7 mi away
      3 BR / 4 BA / Sleeps 8 | Quick view

      Details

      N/A
      • Fireplace
      • A/C or climate control
      • Balcony or terrace
      • Parking
      • Grill
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      4 BR / 4 BA / Sleeps 10

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      916 Langdon Court

      Annapolis house – 19.5 mi away
      4 BR / 4 BA / Sleeps 10 | Quick view

      Details

      N/A
      • Fireplace
      • A/C or climate control
      • Balcony or terrace
      • Parking
      • Grill
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      0 BR / 0 BA / Sleeps 1

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      513 Sixth St

      Annapolis house – 19.4 mi away
      0 BR / Sleeps 1 | Quick view

      Details

      This delightful two bedroom two bath home with it's old world charm, delightful new kitchen, offers every amenity. The garden is most charming in Spring, Summer and Fall and a panorama of lovliness in the snow of Winter. Walking distance to City dock, The Academy, best resturants and shopping. The Maritime Museum here…
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask
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