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$900

8 BR / 6 BA / Sleeps 16

Maryland Eastern Shore Waterfront Estate - Easton vacation rentals
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$900

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Maryland Eastern Shore Waterfront Estate

8 BR / 6 BA / Sleeps 16 | Quick view

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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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$90

3 BR / 3 BA / Sleeps 6

2 Reviews

$90

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Waterfront Vacation Room Rentals

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

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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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$209

2 BR / 1 BA / Sleeps 6

Love Point Bay Vacation Home - Easton vacation rentals
1 / 11

$209

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Love Point Bay Vacation Home

2 BR / 1 BA / Sleeps 6 | Quick view

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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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$300

4 BR / 2 BA / Sleeps 8

3 Reviews

$300

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Waterfront house Eastern Shore Chesapeake Bay

4 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 3 Reviews

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Reviews

(3)

This house is on the former estate of John Raskob, builder of the Empire State Building. The four-bedroom, two-bath house is one of seven that Raskob built for his farm employees. Now it has its own dock and swimming pool fronting on Grove Creek, with access to the Chester River and Chesapeake Bay. The property is …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Fireplace
  • Housekeeping Optional
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(3)

Stress-free environment

Left on Jan 30, 2013 for a stay in July 2011

We have stayed at alan Fisher's Grove Creek home five times in the past six years and have enjoyed every stay. The home and grounds provide a stress-free environment that we look forward to each and every year. It is private and completely furnished with everything you need. All you require are your jeans and bathing suits. There is nothing like waking up in the morning and enjoying a few laps in…

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$250

3 BR / 4 BA / Sleeps 8

1 Reviews

$250

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ENDLESS SUNSETS - The perfect getaway!

3 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 1 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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$450

4 BR / 3 BA / Sleeps 10

Chesapeake Bay Luxury Vacation Home, 5 Star - Easton vacation rentals
1 / 12

$450

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Chesapeake Bay Luxury Vacation Home, 5 Star

4 BR / 3 BA / Sleeps 10 | Quick view

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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 / 3 BA / Sleeps 10

5 Reviews

$450

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Beautiful St. Michaels House Steps from Water and Town

3 BR / 3 BA / Sleeps 10 | Quick view
“ Excellent ” 5 Reviews

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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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$575

4 BR / 4 BA / Sleeps 14

1 / 23

$575

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Chesapeake Bay Spectacular

4 BR / 4 BA / Sleeps 14 | Quick view

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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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$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

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 3 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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$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

4 BR / 3 BA / Sleeps 10 | Quick view

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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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$295

4 BR / 3 BA / Sleeps 8

1 / 6

$295

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Downtown Annapolis !

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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$375

4 BR / 3 BA / Sleeps 10

1 Reviews

$375

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Sandy Pines: Enjoy Harris Creek w/Pool and Boats

4 BR / 3 BA / Sleeps 10 | Quick view
“ Excellent ” 1 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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$500

6 BR / 3 BA / Sleeps 18

6 Reviews

$500

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Chesapeake Bay Waterfront, Private Dock, Beach

6 BR / 3 BA / Sleeps 18 | Quick view
“ Excellent ” 6 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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$200

4 BR / 2 BA / Sleeps 8

1 / 18

$200

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Snug Harbor USNA Cottage in Eastport Annapolis

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

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$164

3 BR / 2 BA / Sleeps 8

1 / 49

$164

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Fun DC/Annaoplis Chesapeake Waterfront Cottge

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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$400

3 BR / 2 BA / Sleeps 8

1 / 7

$400

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Charming Townhouse - Steps to City Dock and USNA

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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$250

3 BR / 1 BA / Sleeps 7

1 / 20

$250

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Visit your Midshipman

3 BR / 1 BA / Sleeps 7 | Quick view

Details

Charming 3BR 1BA cape cod is 1 1/2 miles from City Dock and USNA. Enjoy the large back yard with two-level patio, hot tub and fire pit. Master bedroom has king bed. Second bedroom has a queen sized bed. Air mattress available in office for third bedroom. Additional queen air mattress available to sleep a total of…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

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$250

3 BR / 6 BA / Sleeps 10

1 / 22

$250

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WATERFRONT SUISSE CHALET

3 BR / 6 BA / Sleeps 10 | Quick view

Details

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
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - 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

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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$190

3 BR / 1 BA / Sleeps 5

1 / 41

$190

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"The Cottage" Cambridge Chesapeake Waterfront Home

3 BR / 1 BA / Sleeps 5 | Quick view

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"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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$280

4 BR / 2 BA / Sleeps 8

2 Reviews

$280

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Peaceful, Waterfront Home w/Pier on Kent Island

4 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 2 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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$375

4 BR / 4 BA / Sleeps 10

1 / 37

$375

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Luxury vacation condominum with private beach

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

4 BR / 4 BA / Sleeps 8

1 / 13

$500

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10 Minute Walk to Dwtn or Use Free Shuttle!

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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$450

3 BR / 3 BA / Sleeps 8

1 / 18

$450

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Historic Waterfront Property with Wi-Fi and Dock

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

3 BR / 2 BA / Sleeps 6

1 Reviews

$250

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Charming Vintage Cottage/secluded Yard/Walk. WIFI

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 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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$1,500

0 BR / 4 BA / Sleeps 6

1 / 7

$1,500

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Eastern Shore Vacation Rental

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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$449

6 BR / 5 BA / Sleeps 16

9 Reviews

$449

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Stunning, Newer Chesapeake Waterfront Rental

6 BR / 5 BA / Sleeps 16 | Quick view
“ Excellent ” 9 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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$360

7 BR / 4 BA / Sleeps 11

2 Reviews

$360

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Large Historic Home On Harbor in St. Michaels

7 BR / 4 BA / Sleeps 11 | Quick view
“ Excellent ” 2 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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$1,100

7 BR / 6 BA / Sleeps 28

5 Reviews

$1,100

Inquire

Yr Round Estate on Bay / Family Reunions Sleeps 28

7 BR / 6 BA / Sleeps 28 | Quick view
“ Excellent ” 5 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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$250

2 BR / 2 BA / Sleeps 4

1 / 8

$250

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Waterfront Boat Vacation Rental

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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$195

2 BR / 2 BA / Sleeps 4

1 Reviews

$195

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Premier Cottage in St. Michaels- In Town Location!

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 1 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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$375

2 BR / 1 BA / Sleeps 6

1 Reviews

$375

Inquire

Cottage 2 at Grandview Pleasure Point

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 1 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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$190

2 BR / 2 BA / Sleeps 5

12 Reviews

$190

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Location Location! St Michaels-- In Town Cottage!

2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 12 Reviews

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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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$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

5 BR / 4 BA / Sleeps 18 | Quick view
“ Excellent ” 2 Reviews

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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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$449

7 BR / 5 BA / Sleeps 18

11 Reviews

$449

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Waterfront Chespeake Bay Retreat

7 BR / 5 BA / Sleeps 18 | Quick view
“ Excellent ” 11 Reviews

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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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$665

4 BR / 3 BA / Sleeps 13

8 Reviews

$665

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Grandview Mainhouse

4 BR / 3 BA / Sleeps 13 | Quick view
“ Excellent ” 8 Reviews

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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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$250

3 BR / 2 BA / Sleeps 6

1 Reviews

$250

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Unique, Affordable Nature-Oriented Getaway Home

3 BR / 2 BA / Sleeps 6 | Quick view
“ Average ” 1 Reviews

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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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    $175

    3 BR / 2 BA / Sleeps 10

    10 Reviews

    $175

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    Ocean City, MD - Time n Tide Unit #1 (OCEAN BLOCK)

    3 BR / 2 BA / Sleeps 10 | Quick view
    “ Excellent ” 10 Reviews

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    Reviews

    (10)

    OCEAN CITY, MARYLAND: 26th St - Steps to beach w/POOL (RENT TO HIGH SCHOOL SENIORS) The Time-n-Tide building is located at the quiet end of the boardwalk in Ocean City, Maryland. Condo has an unblocked southern exposure and the BEACH and BOARDWALK is less than 200 yards from the front door. The complex has a fenced …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (10)

    Great Getaway Place

    Left on Jun 23, 2011 for a stay in May 2011

    We rented the unit for a family re-union. The three bedrooms were spacious and everything in the place was brand new. Of all the places we looked at in OC this one had everything we were looking for. It was only one block to the beach, had ample parking, great front porch with plenty of room to eat outside and the owners couldn't do enough for us. The whole complex with it's pool and fenced in …

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    $280

    3 BR / 3 BA / Sleeps 6

    1 / 9

    $280

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    RESTORED WATERFRONT COTTAGE

    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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    $595

    5 BR / 3 BA / Sleeps 20

    1 / 26

    $595

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    Annapolis Crows Nest Cottage: Chesapeake Bay View

    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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    $800

    3 BR / 3 BA / Sleeps 10

    1 Reviews

    $800

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    Beautifully water front Contemporary Home in Bay Ridge, Annapolis

    3 BR / 3 BA / Sleeps 10 | Quick view
    “ Excellent ” 1 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

    1 BR / 2 BA / Sleeps 3

    1 Reviews

    $250

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    Tilghman Landing

    1 BR / 2 BA / Sleeps 3 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    Watch the dazzling sunsets over the bay. Choose from our one bedroom Waterfront Cottages located on the Chesapeake Bay side of Tilghman Island: It is a beautiful 2-story one bedroom cottage with stunning views of the bay from the 2nd floor bedroom, with hardwood floors throughout, a full kitchen, satellite TV, DVD …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Outdoor Dining Area
    • A/C or climate control
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    Get away weekend with friends

    Left on Jul 17, 2014 for a stay in June 2014

    Have stayed here two times. Once in the 2 bedroom and once in the one bedroom. Both facilities are clean and welcoming. Both properties provide beautiful views and easy access to the docks and bay. The owners are very nice and also host a fun crab feast on Saturday evenings.

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    $250

    2 BR / 1 BA / Sleeps 4

    1 / 12

    $250

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    2 Bedroom Unique Private Waterfront Escape

    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
    • Internet Access
    • Washing Machine
    • Clothes Dryer

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