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Holiday villas in Sherwood, MD

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All 15 Rentals in the Sherwood Area
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The following rentals are within 15 kilometers of Sherwood, Maryland.

From
€221
Per Night
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1 / 11
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Tilghman
1 Bedroom, 1 Bathroom, Sleeps 3
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From
€399
Per Night
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1 / 13
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St. Michaels
3 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
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From
€155
Per Night
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1 / 20
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Tilghman
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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From
€332
Per Night
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1 / 22
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St. Michaels
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
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From
€66
Per Night
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1 / 21
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Tilghman
2 Bedrooms, 1 Bathroom, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Get away and stay in our cozy cottage that sits on the Knapp's Narrows in Tilghman, MD. Captain's Watch is a Waterfront Cottage which has a screened porch with beautiful sunrise view of Knapps Narrows. It is nestled in a Working Watermens Village, 12 miles from Historic St. Michaels, Maryland on... View all property information
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From
€221
Per Night
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1 / 14
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Oxford
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Beautifully renovated home sleeps 6. Full master suite with sitting area, steam shower & soaking tub. Second bedroom has full-sized bed. Queen sized murphy bed in den. Chef's kitchen with five burner stove & side warming oven and four-person breakfast counter. Wood-burning stove in living room,... View all property information
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From
€1,328
Per Night
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1 / 7
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Oxford
Studio, 4 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Fishing...
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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. View all property information
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From
€672
Per Night
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1 / 38
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St. Michaels
6 Bedrooms, 6 Bathrooms, Sleeps 12
Bookings
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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
€257
Per Night
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1 / 23
St. Michaels
7 Bedrooms, 3 Bathrooms, Sleeps 11
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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
  • ?
  • 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 27 September 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 23 July 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
€142
Per Night
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1 / 13
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 19 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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From
€332
Per Night
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1 / 9
Bozman
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (1) Make Enquiry
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
€589
Per Night
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1 / 7
Bozman
4 Bedrooms, 2 Bathrooms, Sleeps 13
Details Reviews (8) Make Enquiry
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
€133
Per Night
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1 / 20
St. Michaels
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Reviews (12) Make Enquiry
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 22 August 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 20 July 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
€221
Per Night
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1 / 11
Claiborne
3 Bedrooms, 4 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
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 11 October 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
€248
Per Night
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1 / 9
St. Michaels
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
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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Suitability

  • Wheelchair access (1)
  • Elder access (6)
  • Suitable for children (0)
  • Pet friendly (6)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (14)
  • Internet (14)
  • Grill (13)
  • Other outdoor space (13)
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