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$900

8 BR / 6 BA / Sleeps 16

Maryland Eastern Shore Waterfront Estate - Claiborne 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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$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

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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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$750

6 BR / 5 BA / Sleeps 13

2 Reviews

$750

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Charming and Spacious Annapolis Victorian

6 BR / 5 BA / Sleeps 13 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

The Perfect House for a Navy Football Game Weekend!! This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. With six bedrooms (two queen beds, three fulls and two twins) the house could comfortably sleep up to 12. Additional rooms include a pool table …
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Deck
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

Charming house in a great location! Perfect for larger group!

Left on Aug 11, 2014 for a stay in August 2014

We just returned from our sailing weekend in Annapolis and had an amazing time staying at this lovely house for the weekend. The house was perfect for a larger group. The large deck out back and patio furniture were wonderful for grilling and eating dinner outside. (The outdoor giant Jenga was a hit!) We went with a group of various couples and a couple of our single friends and everyone had …

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$209

2 BR / 1 BA / Sleeps 6

Love Point Bay Vacation Home - Claiborne 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

    3 BR / 3 BA / Sleeps 6

    Annapolis Waterfront South River Chesapeake Bay - Claiborne vacation rentals
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    $300

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    Annapolis Waterfront South River Chesapeake Bay

    3 BR / 3 BA / Sleeps 6 | Quick view

    Details

    You'll love the stunning 180-degree view of the South River, just off the Chesapeake Bay near Annapolis. The location is incredible. Just six miles from Annapolis and the United States Naval Academy. The home is 15 miles from Baltimore/Washington International Airport and 40 minutes to Washington, D.C. (15 miles to …
    • Waterfront
    • Hot Tub/Jacuzzi
    • Internet Access
    • Fireplace
    • Washing Machine
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $222

    4 BR / 3 BA / Sleeps 10

    Marshall Haus - Claiborne vacation rentals
    1 / 22

    $222

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    Marshall Haus

    4 BR / 3 BA / Sleeps 10 | Quick view

    Details

    Marshall Haus Travel to a unique comfortably furnished round house in a secluded Caribbean paradise, featuring excellent snorkeling, fishing, and diving from a mile long white powder sand beach. Located in the vicinity of the quaint settlement of Current, Eleuthera population 130, an ideal getaway from the hustle and …
    • Waterfront
    • Internet Access
    • Washing Machine
    • Parking
    • Grill
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $169

    3 BR / 2 BA / Sleeps 4

    2 Reviews

    $169

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    Spacious, Modern Condo nr. Navy Stadium and Mall

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

    Details

    Reviews

    (2)

    Large, open third floor condominium with cathedral ceilings. Large master bedroom has queen bed. 2nd bedroom has twin beds. Large loft has queen size bed. Although the condo can accommodate 6 for sleeping, I will rent only to parties of 4 or fewer. Dining room can seat 8 + Washer and Dryer, ironing board. Microwave…
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Central heating
    • Pet friendly - ask
    • Suitable for children

    Details

    Reviews

    (2)

    Great place, great location and great price

    Left on Nov 12, 2013 for a stay in November 2013

    My family of four stayed there for the weekend. We were there to watch the Navy-Hawaii football game. We could not find any hotel rooms in/around Annapolis that could host a family of four. We took a chance on this condo and it was awesome. It was less expensive than a hotel room and we each had our own room and could cook our own meals. The location had easy access to the football game, the…

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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

    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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    $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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    $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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    $450

    4 BR / 3 BA / Sleeps 10

    1 / 12

    $450

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    Chesapeake Bay Luxury Vacation Home, 5 Star

    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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    $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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    $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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    $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

    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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    $350

    3 BR / 2 BA / Sleeps 6

    1 / 25

    $350

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    *BOOK NOW* Beautiful Cottage in historic Annapolis

    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. Sun Porch & Plenty of parking. A perfect place to relax and enjoy Annapolis, the property is available all year around with a minimum …
    • Wireless Internet
    • Fireplace
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Suitable for children - ask

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    $1,500

    4 BR / 4 BA / Sleeps 10

    1 / 15

    $1,500

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    1. Private 20 acre waterfront estate - main house

    4 BR / 4 BA / Sleeps 10 | Quick view

    Details

    Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation and building addition with exposed structure and mechanical systems that serves as the architect - owner's live-work getaway. The main house has a 4 stop elevator, 2 car garage, master bdrm and bath suite, 3 additional large bedrooms, and …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible

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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

    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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    $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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    $250

    3 BR / 2 BA / Sleeps 10

    1 / 10

    $250

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    Shelwood Baie

    3 BR / 2 BA / Sleeps 10 | Quick view

    Details

    North Beach, known as "The Jewel of the Chesapeake", is a small bayside town with a village feel. There is a fabulous farmers market on Friday evenings starting in April, shops and restaurants to explore, wine tastings, an art gallery, a boardwalk perfect for a stroll along the beach, bicycles for rent, a …
    • Wireless Internet
    • Outdoor Dining Area
    • A/C or climate control
    • Central heating
    • Balcony or terrace
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly - ask

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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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    $250

    4 BR / 3 BA / Sleeps 10

    1 / 12

    $250

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    Million dollar view on the Chesapeake

    4 BR / 3 BA / Sleeps 10 | Quick view

    Details

    Fredelig sted"(peaceful place) is patterned after a Norwegian cottage with curved roof on the outside and knotty pine and birch wood inside. The bright panoramic view of the Chesapeake from the great room, master bedroom or deck elicits a relaxed, peaceful mood as soon as you arrive. Watch the seagulls or osprey …
    • Waterfront
    • A/C or climate control
    • Porch
    • Parking
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask

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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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    $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 / 2 BA / Sleeps 6

    1 / 9

    $250

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    Renovated Luxury Waterview House

    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    This charming restored cottage has all the luxury upgrades you could want!! Gourmet kitchen with granite counters and double-oven, 5-burner gas cooktop, and plenty of storage. Easy-to-enjoy gas fireplace, and ample space for entertaining and kids to play -- both indoors and out! Convenient to beach, boardwalk, …
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Suitable for children

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    $225

    3 BR / 3 BA / Sleeps 7

    1 / 18

    $225

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    My Seaside Cottage and La Petite Maison

    3 BR / 3 BA / Sleeps 7 | Quick view

    Details

    My Seaside Cottage and La Petite Maison Located on beautiful, secluded North Beach of Current, Eleuthera, our 2-bedroom cottage is situated in the vicinity of the quaint settlement of Current, Eleuthera population 130, an ideal getaway from the hustle and bustle of 21st Century living. A 10 minute drive to the ferry …
    • Waterfront
    • Parking
    • Grill
    • Towels Provided
    • Microwave
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $350

    3 BR / 7 BA / Sleeps 10

    1 / 22

    $350

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    WATERFRONT SUISSE CHALET

    3 BR / 7 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
    • Pet friendly - ask
    • 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

    PreviousNext property

    $100

    1 BR / 1 BA / Sleeps 5

    5 Reviews

    $100

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    1 bedroom cottage near water, dog friendly

    1 BR / 1 BA / Sleeps 5 | Quick view
    “ Excellent ” 5 Reviews

    Details

    Reviews

    (5)

    The Seahorse Guest Cottage is located in North Beach, Maryland, on the western shore of the Chesapeake Bay, within an hour’s drive of Washington, Baltimore, and Annapolis. The fully furnished cottage has a living room with sofabed, bedroom with queen size bed, sunporch with day bed, a full kitchen, and a backyard …
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (5)

    Quiet and peaceful!

    Left on Sep 26, 2011 for a stay in September 2011

    We had a very nice stay at Seahorse cottage. It was on a quiet street, but only a short walk to the boardwalk. The owners are wonderful to talk to. We hope to go back next year for our anniversary.

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    $250

    3 BR / 2 BA / Sleeps 6

    1 / 23

    $250

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    TreeHouse

    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Comfortable Timber Frame deep waterfront home in Annapolis close to USNA. Private wooded setting with wonderful water views. 3 miles to Annapolis Historic district. Easy commute to Washington, DC and Baltimore, MD. Tastefully furnished and equipped.
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Suitable for children - ask
    • Suitable for the elderly - ask

    PreviousNext property

    $425

    4 BR / 3 BA / Sleeps 9

    2 Reviews

    $425

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    Beautiful Murray Hill Home (Annapolis)

    4 BR / 3 BA / Sleeps 9 | Quick view
    “ Excellent ” 2 Reviews

    Details

    Reviews

    (2)

    Our beautifully-appointed home pays homage to the Colonial Period. It comfortably sleeps eight guests with four bedrooms and 2.5 baths. It boasts elegant dining and living rooms. Enjoy the quiet street and an easy stroll to downtown Annapolis. We have taken great care and paid pain-staking attention to detail to …
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (2)

    Comfortable and secure in a great home - almost as good as at ho

    Left on Nov 03, 2013 for a stay in October 2013

    The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town.

    We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies.

    We certainly will attempt…

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    $295

    3 BR / 3 BA / Sleeps 8

    3 Reviews

    $295

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    Retreat at a quiet, water front cottage

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

    Details

    Reviews

    (3)

    Located close to both Chestertown (15 minutes) and Rock Hall (30 minutes), MD this quiet, simple but energetic space is an ideal gathering place for families and friends. Stay here and relax the entire visit or explore the many activities, restaurants and cultural venues available in the Kent County area. This south …
    • Waterfront
    • Ocean or water views
    • Wireless Internet
    • Fireplace
    • Washing Machine
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (3)

    Construction in progress and mud everywhere.

    Left on Oct 18, 2014 for a stay in October 2014

    If the unit is under construction, do not rent it. We should have been notified of the construction and given the opportunity to cancel.

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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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    $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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    $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

    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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    $249

    2 BR / 2 BA / Sleeps 5

    1 / 17

    $249

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    Chesapeake Bay House

    2 BR / 2 BA / Sleeps 5 | Quick view

    Details

    Outstandingly beautiful and immaculately maintained light-filled custom-built home with stunning, unobstructed views of the wonderful Chesapeake Bay in the picturesque town of North Beach. Steps away from the boardwalk in front of the bay. Within a 45-min drive from Washington DC (just 33 miles), Baltimore & Annapolis…
    • Waterfront
    • Hot Tub/Jacuzzi
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask

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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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    $350

    4 BR / 2 BA / Sleeps 10

    1 / 21

    $350

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    Easy access to Annapolis, Washington DC, Baltimore

    4 BR / 2 BA / Sleeps 10 | Quick view

    Details

    Clean, comfortable, family-friendly split-level home, fully furnished, washer and dryer, TV, cable, internet, wifi, quiet neighborhood with off-street parking, large shaded fenced back yard with deck for relaxing after a fun-filled day exploring Historic Annapolis, the Baltimore Harbor or our Nation's Capitol. #1BR-…
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible - ask

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      $850

      4 BR / 4 BA / Sleeps 14

      1 / 24

      $850

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      Amazing Waterfront in Annapolis

      4 BR / 4 BA / Sleeps 14 | Quick view

      Details

      A Peaceful Oasis Overlooking Annapolis Waterfront and easy walking distance to downtown. This incredible home has 100’ of floor-to-ceiling windows nestled in the tree canopy for expansive views of Weems Creek. Decks span the entire house 65' above the water. There are 4 full baths and 4 bedrooms with 2 kings, 2 …
      • Waterfront
      • Hot Tub/Jacuzzi
      • Internet Access
      • Fireplace
      • Washing Machine
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible

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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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      $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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      $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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      $360

      7 BR / 4 BA / Sleeps 11

      2 Reviews

      $360

      Inquire

      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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      $500

      1 BR / 2 BA / Sleeps 4

      1 / 11

      $500

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      3. Private 20 acre waterfront estate - live-work

      1 BR / 2 BA / Sleeps 4 | Quick view

      Details

      This is the newly renovated 3-story open plan live-work unit that is connected to the main house that is similarly titled as the main house (1) and the studio apartment (2) - not included with this listing. Striking and dramatic 1500 - 1600 sf contemporary, open plan loft style renovation with a open bridge …
      • Pet friendly - ask
      • Suitable for children - ask

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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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      $375

      2 BR / 1 BA / Sleeps 6

      1 Reviews

      $375

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      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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      $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

      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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      $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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      $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

      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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        $190

        2 BR / 2 BA / Sleeps 5

        12 Reviews

        $190

        Inquire

        Location Location! St Michaels-- In Town Cottage!

        2 BR / 2 BA / Sleeps 5 | Quick view
        “ Excellent ” 12 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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        $449

        7 BR / 5 BA / Sleeps 18

        11 Reviews

        $449

        Inquire

        Waterfront Chespeake Bay Retreat

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