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Vacation Rentals in Grasonville, MD and nearby

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All 44 Rentals in the Grasonville Area
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From
$450
Per Night
1 / 12
Grasonville
4 Bedrooms, 3 Bathrooms, Sleeps 10
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The following rentals are within 15 miles of Grasonville, Maryland.

From
$750
Per Night
1 / 26
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Annapolis
6 Bedrooms, 5 Bathrooms, Sleeps 13
Bookings
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From
$375
Per Night
1 / 22
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St. Michaels
4 Bedrooms, 3 Bathrooms, Sleeps 10
Booking
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From
$400
Per Night
1 / 30
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Annapolis
4 Bedrooms, 3 Bathrooms, Sleeps 9
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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From
$800
Per Night
1 / 31
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Annapolis
3 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
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From
$759
Per Night
1 / 38
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St. Michaels
6 Bedrooms, 6 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
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... View all property information
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From
$280
Per Night
1 / 3
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Annapolis
4 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Fireplace
  • Garden or Yard
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Unique Bed and Breakfast One of the oldest residences in Annapolis with all modern amenities. Best Breakfast! Perfect for USNA and St. John's families Wonderful hosts! View all property information
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From
$169
Per Night
1 / 4
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Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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,... View all property information
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5 of 5 stars Reviewed June 29, 2014
We really enjoyed our stay at your condo. It was roomy and felt like home. It is in a very nice condo community which was very quiet. It was nice being able to cook and see into...
5 of 5 stars Reviewed November 12, 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...
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From
$300
Per Night
1 / 9
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Annapolis
1 Bedroom, 1 Bathroom, Sleeps 2
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
This is the newly renovated 780 sf studio unit that is on the ground floor of a main house that is similarly titled and on the same property. Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation of the main house with exposed structure and mechanical systems that serves as... View all property information
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From
$1,500
Per Night
1 / 15
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Annapolis
4 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
About this property
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... View all property information
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From
$500
Per Night
1 / 11
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Annapolis
1 Bedroom, 2 Bathrooms, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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... View all property information
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From
$175
Per Night
1 / 14
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Annapolis
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
PLEASE CONTACT US BEFORE BOOKING FOR USNA GRADUATION and BOAT SHOWS (Rates May Vary) PLEASE NOTE WE ARE NOT TAKING RESERVATIONS FOR USNA GRADUATION 2015-2016 Large 1 BR 1 BA apartment with den/study (single pull-out daybed available), large and bright living room with pull-out sofa, and three... View all property information
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From
$295
Per Night
1 / 6
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Annapolis
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
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... View all property information
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From
$450
Per Night
1 / 13
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St. Michaels
3 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
Details Reviews (5) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
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,... View all property information
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5 of 5 stars Reviewed September 9, 2014
The home was absolutely beautiful. Right around the corner from the town. Perfect location! We had been to St. Michaels 3 times before this trip and now we finally found our...
5 of 5 stars Reviewed August 19, 2014
Very comfortable, well furnished and equipped house with both modern and historical features. We took advantage of the great location to walk to tourist sites, restaurants and...
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From
$400
Per Night
1 / 7
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Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
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From
$250
Per Night
1 / 17
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Rock Hall
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This Spacious Home provides 3 Bedrooms and 2 bathrooms. Each room sleeps 2 people comfortably, and an old fashion cot is provided to sleep one more. This home is completely equipped with all the comforts of home. The Central location is in the heart of the Marina district, steps from Waterman’s... View all property information
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From
$250
Per Night
1 / 12
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Easton
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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... View all property information
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From
$695
Per Night
1 / 25
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Annapolis
5 Bedrooms, 3 Bathrooms, Sleeps 20
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Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Private Fishing...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
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... View all property information
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From
$250
Per Night
1 / 15
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Rock Hall
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
The Cottage takes advantage of its unique environment with a large deck overlooking the extensive lawn and the tranquil waters of Spring Cove. The deck includes a dining set and barbeque grill.The first level includes a screened porch accessed through a first floor bedroom The Cottage is oriented... View all property information
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4 of 5 stars Reviewed September 16, 2014
My sisters and mother stayed three nights in this quaint house with great views of one of the marina's and cove area. The downstairs was perfect my mother, with a screened in...
4 of 5 stars Reviewed August 19, 2014
My family was looking for a relaxing getaway that would be an alternative to another week at the beach. We found the perfect spot at this cottage near Rock Hall. We rented with no...
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From
$250
Per Night
1 / 20
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Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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 & 3 blocks from Spa Creek, is this charming, cozy, easy-living place to relax, entertain & enjoy nature. Plenty of free parking- two... View all property information
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5 of 5 stars Reviewed July 15, 2014
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...
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From
$180
Per Night
1 / 12
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Rock Hall
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Enjoy the gentle tidal waters of the Chesapeake Bay and its tributaries from your private overlook. The Captain’s Quarters at Spring Cove is a crisp and contemporary second floor living space with great water views. An exterior stairway leads to an ample deck where you can enjoy breakfast and... View all property information
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From
$700
Per Night
1 / 6
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Annapolis
5 Bedrooms, 6 Bathrooms, Sleeps 12
Booking
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Garden or Yard
  • Grill
  • Housekeeping...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Our home is brand new & only one block from the Naval Academy Stadium on Gibson Rd (you can see the stadium from M. bedroom balcony). With, 4 bedrooms upstairs & 1 bedroom down, all the bedrooms have their own full bath. There is also a family room on the second floor with a mini bar, sink & pull... View all property information
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From
$150
Per Night
1 / 18
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Annapolis
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
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... View all property information
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From
$209
Per Night
1 / 11
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Stevensville
2 Bedrooms, 1 Bathroom, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
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... View all property information
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From
$250
Per Night
1 / 20
Payment Protection
Annapolis
3 Bedrooms, 1 Bathroom, Sleeps 7
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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From
$180
Per Night
1 / 21
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Chester
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
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... View all property information
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5 of 5 stars Reviewed July 29, 2013
First I would like to say thanks, to Harry, and Scott. They were the best host, I've encountered. They have a property, they can be proud of. The house was just excellent. The...
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From
$171
Per Night
1 / 28
Centreville
4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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From
$375
Per Night
1 / 9
Bozman
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Fireplace
  • Grill
  • Internet Access
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
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From
$665
Per Night
1 / 7
Bozman
4 Bedrooms, 2 Bathrooms, Sleeps 13
Details Reviews (8) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
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From
$290
Per Night
1 / 12
St. Michaels
7 Bedrooms, 3 Bathrooms, Sleeps 11
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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5 of 5 stars Reviewed September 27, 2014
Friends and family stayed at the home to watch my nephew get married on 9/20/14. I must say, the house was as much of the event as the wedding celebration. We went from 6 of us...
5 of 5 stars Reviewed July 23, 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...
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From
$150
Per Night
1 / 20
St. Michaels
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Reviews (12) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
The historic Washington Melson House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from all museums, parks, restaurants, churches and shops in St. Michaels. The house was built around 1840 by Washington Melson, a sailor, believed to be one of two individuals in Talbot County... View all property information
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5 of 5 stars Reviewed August 22, 2014
The pictures of this house do not lie. It is that nice. We parked our car and didn't need again until we left. Close to everything. Walk to the water , sit on the bench and...
5 of 5 stars Reviewed July 20, 2014
We fully enjoyed our relaxing stay in the sleepy little town of St. Michaels, and would definitely return when given the chance. The location is perfect - within a one block walk...
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From
$160
Per Night
1 / 7
St. Michaels
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The historic Thomas Blades House is a 2 bedroom, 2 bathroom vacation cottage that is a short walk from all museums, parks, restaurants, churches and shops in St. Michaels. The house was built around 1850 by Thomas Blades, a young sailor. The first floor of the original portion of the Blades... View all property information
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5 of 5 stars Reviewed August 18, 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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From
$250
Per Night
1 / 23
Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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. View all property information
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From
$250
Per Night
1 / 11
Claiborne
3 Bedrooms, 4 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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5 of 5 stars Reviewed October 10, 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...
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From
$850
Per Night
1 / 24
Annapolis
4 Bedrooms, 4 Bathrooms, Sleeps 14
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
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... View all property information
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From
$575
Per Night
1 / 23
Centreville
4 Bedrooms, 4 Bathrooms, Sleeps 14
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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From
$1,429
Per Night
1 / 16
St. Michaels
6 Bedrooms, 7 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Tidewater Vacations Inc on the Eastern Shore presents another luxurious waterfront vacation home. This is where your dreams come true! Your vacation begins with a drive down a country lane surrounded by farmland or perhaps even arriving on your own helicopter. You have entered another world – one... View all property information
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From
$375
Per Night
1 / 37
Chester
4 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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From
$280
Per Night
1 / 9
St. Michaels
3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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From
$1,143
Per Night
1 / 16
St. Michaels
6 Bedrooms, 5 Bathrooms, Sleeps 12
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Tidewater Vacations Inc on the Eastern Shore presents another luxurious waterfront home. Only minutes from the famous historic “Chestertown”, this magnificent 1000 acre estate is both a wildlife sanctuary and arboretum, with hundreds of mature specimen trees and acres of woods and farm fields. The... View all property information
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From
$5,250
Per Week
1 / 16
St. Michaels
5 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Another luxury vacation rental home by Tidewater Vacations Inc on the Eastern Shore. This gorgeous, traditional country home is nestled amongst trees on magnificent grounds overlooking the Wye River.The secluded estate is ideally located close to the historic towns of Easton and St Michaels and... View all property information
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From
$714
Per Night
1 / 11
St. Michaels
5 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Tidewater Vacations in St Michaels is excited to present the Virginia (also known as Duxbury Point Manor as one of our more popular vacation homes on the water near St Michaels This enchanting Manor home overlooking the broad waters of Leadenham Bay, has a pool, a dock and a floating 18ft dock... View all property information
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From
$5,500
Per Week
1 / 16
St. Michaels
5 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Tidewater Vacations of St Michaels presents a historic, charming vacation rental just minutes from Easton and St Michaels. Savanna is truly one of Maryland’s oldest and most picturesque vacation rental homes on the Miles River in Talbot County. Dating from 1659 and throughout the years, Savanna... View all property information
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From
$400
Per Night
1 / 13
Annapolis
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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Suitability

  • Wheelchair access (6)
  • Elder access (13)
  • Suitable for children (8)
  • Pet friendly (16)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (37)
  • Other outdoor space (37)
  • Internet (35)
  • Washer/Dryer (35)
  • Grill (34)
  • View all amenities