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Vacation Rentals in Sherwood, MD and nearby

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    All 23 Rentals in the Sherwood Area
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    The following rentals are within 25 kilometres of Sherwood, Talbot County, Maryland.

    From
    $199
    / Night
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    1 / 17
    4.5 of 5 stars (5) Very good
    North Beach, MD
    1 Bedroom / 1 Bathroom / Sleeps 5
    other travellers have booked this property
    Overview Reviews (5) Make Enquiry
    From
    $331
    / Night
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    1 / 9
    North Beach, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    From
    $232
    / Night
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    1 / 20
    5 of 5 stars (4) Excellent
    Tilghman
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    other travellers have booked this property
    Overview Reviews (4) Make Enquiry
    From
    $166
    / Night
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    1 / 21
    Tilghman
    2 Bedrooms / 1 Bathroom / Sleeps 6
    other traveller has booked this property
    Overview Make Enquiry
    Amenities & Details
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    Tilghman, Talbot County 21671
    From
    $277
    / Night
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    1 / 11
    Stevensville, MD
    2 Bedrooms / 1 Bathroom / Sleeps 6
    other travellers have booked this property
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    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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    Location Information
    Stevensville, Kent Island 21666
    From
    $398
    / Night
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    1 / 20
    5 of 5 stars (1) Excellent
    Easton
    2 Bedrooms / 1 Bathroom / Sleeps 4
    other traveller has booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Water Views
    • Satellite TV
    • Dryer
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • 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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    Location Information
    Easton, Talbot County 21601
    5 of 5 stars Reviewed 25 July 2015
    This was beyond what I could of hoped for in every way. I actually think the photos on the listing do not do it justice. The property was so tranquil and beautiful. The owner is...
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    $331
    / Night
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    1 / 17
    Tilghman
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • There Are Tennis...
    • Ocean Views
    • Wi-Fi
    • Water Views
    • Watersports Nearby
    • Satellite TV
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in the heart of the classic waterman's village of Tilghman Island, this gorgeous Knapps Narrows waterfront home comes complete with a boat slip! Watch the boats stream by, fish, crab or just relax in this 2700 sq ft home. This stunning vacation home boasts an open floor-plan, gourmet... View all property information
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    Location Information
    Tilghman, Talbot County 21671
    From
    $795
    / Night
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    1 / 15
    Easton
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Ocean Views
    • Watersports Nearby
    • Air Conditioning
    • Waterfront
    • Private Outdoor...
    • Water Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    4+ acres on Shipshead Creek off of St. Michaels road. Fully furnished (2 king and 4 twin beds), heated pool, deep water dock, tennis court,and pet friendly. Boat, Jet Ski, Paddle Board, Kayak, Canoe, and Bike rentals can be arranged-Inquire if interested The Space Pet Friendly waterfront... View all property information
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    Location Information
    Easton, Talbot County 21601
    From
    $331
    / Night
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    1 / 11
    Neavitt
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Garden
    • Wi-Fi
    • Grill
    • Linens Provided
    • Towels Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Newly renovated cottage in the village of Neavitt. Neavitt is a great village only 10 minutes away from St. Michaels. The house has waterviews and access to it's own personal dock which is great for fishing, kayaking or paddle boarding. Spend the day out on local waterways and then relax the night... View all property information
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    Location Information
    Neavitt, Talbot County 21652
    From
    $224
    / Night
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    1 / 20
    Deale, MD
    2 Bedrooms / 4 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • TV
    • Housekeeping...
    • Water Park Nearby
    • Air Conditioning
    • Wi-Fi
    • Sauna
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Enjoy the home and studio of local sculptor artist. This apartment includes the second and third floors, approximately 2,300 sf of space. Large and comfortable bedrooms, large bathrooms, showers have double heads, sauna in the main master-bath. We provide linens and towels. This apartment has a... View all property information
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    Location Information
    Deale, Maryland 20751
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    From
    $371
    / Night
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    1 / 21
    5 of 5 stars (2) Excellent
    Chester, MD
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Private Fishing...
    • Waterfront
    • Air Conditioning
    • Water Views
    • Fireplace
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    Chester, Kent Island 21619
    5 of 5 stars Reviewed 29 July 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
    $497
    / Night
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    1 / 9
    5 of 5 stars (1) Excellent
    Bozman
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Water Views
    • Fireplace
    • Stereo System
    • Boat Available
    • Air Conditioning
    • Waterfront
    • Internet Access
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • 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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    Location Information
    Bozman, Talbot County 21612
    From
    $881
    / Night
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    1 / 7
    5 of 5 stars (9) Excellent
    Bozman
    4 Bedrooms / 2 Bathrooms / Sleeps 13
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Deck
    • Internet Access
    • Boat Available
    • Air Conditioning
    • Washer
    • Water Views
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • 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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    Location Information
    Bozman, Talbot County 21612
    5 of 5 stars Reviewed 9 June 2015
    Perfectly situated on the water. The views are amazing, as is the pool. There is a huge lawn which is perfect for children of all ages. A short drive to St. Michael's, which is a...
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    From
    $729
    / Night
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    1 / 23
    2 of 5 stars (1) Poor
    Stevensville, MD
    4 Bedrooms / 4 Bathrooms / Sleeps 14
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Deck
    • Stereo System
    • Boat Available
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    Stevensville, Kent Island 21666
    2 of 5 stars Reviewed 4 August 2015
    Let me start off by saying the house was very accommodating for a large party. Myself and some friends rented this location for "guys" weekend. Twelve of us stayed at the house...
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    From
    $331
    / Night
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    1 / 11
    Claiborne
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Waterfront
    • Boat Available
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Claiborne, Talbot County 21663
    From
    $497
    / Night
    View Details
    1 / 37
    Chester, MD
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • Internet Access
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Stereo System
    • Deck
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Chester, Kent Island 21619
    From
    $331
    / Night
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    1 / 11
    4.5 of 5 stars (2) Very good
    Claiborne
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Waterfront
    • Private Outdoor...
    • Internet Access
    • Stereo System
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Claiborne, Talbot County 21663
    4 of 5 stars Reviewed 27 June 2015
    We were a group of two couples each with a young child. There was more than enough room for the 6 of us. The home is well located in Claiborne, about 5 min from downtown...
    5 of 5 stars Reviewed 10 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
    $331
    / Night
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    1 / 12
    Deale, MD
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Refrigerator
    • Air Conditioning
    • Waterfront
    • Grill
    • Stereo System
    • DVD Player
    • Deck
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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... View all property information
    Make Enquiry
    Location Information
    Deale, Maryland 20751
    From
    $497
    / Night
    View Details
    1 / 37
    Chester, MD
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Hot Tub
    • Deck
    • Water Views
    • Internet Access
    • Waterfront
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Chester, Kent Island 21619
    From
    $729
    / Night
    View Details
    1 / 23
    Stevensville, MD
    4 Bedrooms / 4 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Internet Access
    • DVD Player
    • Stereo System
    • Deck
    • Satellite TV
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Make Enquiry
    Location Information
    Stevensville, Kent Island 21666
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    From
    $331
    / Night
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    1 / 12
    Deale, MD
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Waterfront
    • DVD Player
    • Stereo System
    • Air Conditioning
    • Deck
    • Grill
    • Satellite TV
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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... View all property information
    Make Enquiry
    Location Information
    Deale, Maryland 20751
    From
    $596
    / Night
    View Details
    1 / 12
    Grasonville, MD
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Hot Tub
    • Boat Available
    • Stereo System
    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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... View all property information
    Make Enquiry
    Location Information
    Grasonville, Maryland 21638
    From
    $596
    / Night
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    1 / 12
    5 of 5 stars (1) Excellent
    Grasonville, MD
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Internet Access
    • Hot Tub
    • Satellite TV
    • Waterfront
    • Boat Available
    • Air Conditioning
    • DVD Player
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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... View all property information
    Make Enquiry
    Location Information
    Grasonville, Maryland 21638
    5 of 5 stars Reviewed 11 August 2015
    Baydreams backs onto a Chesapeake Bay inlet. The view from the back windows is beautiful and tranquil. We were particularly impressed with a close view of ospreys nesting behind a...
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