Vacation rentals in Sherwood
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Top-rated vacation rentals in Sherwood
Guests agree: these stays are highly rated for location, cleanliness, and more.
Apartment in Stevensville
4.97 out of 5 average rating, 239 reviewsBoutique by the Bay
Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.
Aug 16 – 23
Cottage in Saint Michaels
4.98 out of 5 average rating, 418 reviewsSt. Michaels-Historic Dist. Margaret Wells House
The Margaret Wells House is in the heart of the Historic District between the main street and water. Enjoy a total renovation of this charming home. A short walk to the water's edge, Inn at Perry Cabin, Chesapeake Bay Maritime Museum, restaurants, shops, winery, brewery and local market. A perfect spot for a couple's Shore weekend getaway or attending a wedding, nearby. Our nightly pricing includes coffee, tea, fresh linens on beds, hand-milled natural soap, fresh bath towels and wash cloths.
Mar 19 – 26
Farm stay in Madison
4.98 out of 5 average rating, 159 reviewsMadison Nature Getaway
We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.
Aug 16 – 23
Vacation rentals for every style
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Popular amenities for Sherwood vacation rentals
Other great vacation rentals in Sherwood
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Aug 12 – 19
Home in Saint Michaels
4.91 out of 5 average rating, 151 reviewsSmall Historic House Downtown St Michaels
Dec 21 – 28
Guesthouse in Annapolis
4.9 out of 5 average rating, 202 reviewsCalico Cottage Guest House, king bed, free parking
Nov 14 – 21
Home in Shady Side
5.0 out of 5 average rating, 113 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Mar 18 – 25
Tiny home in Solomons
4.95 out of 5 average rating, 530 reviews“Cabana by the Bay”-tiny home on a pier!
Mar 20 – 27
Home in Cambridge
4.92 out of 5 average rating, 176 reviewsGuest House: Farm homestead
Jul 3 – 10
Bungalow in Deale
4.86 out of 5 average rating, 353 reviewsCozy waterfront getaway on the Bay
Jan 24 – 31
Cottage in North Beach
4.96 out of 5 average rating, 268 reviewsWaterfront Cottage Near Herrington and North Beach
May 1 – 8
Tiny home in Cambridge
4.89 out of 5 average rating, 492 reviewsBlackwater Tiny Cabin on Snakehead Creek
Nov 29 – Dec 6
Home in Annapolis
4.96 out of 5 average rating, 103 reviewsHistoric Downtown in-law suite
Jan 9 – 16
Guesthouse in Annapolis
4.97 out of 5 average rating, 195 reviewsRECENTLY RENOVATED Cottage Near Downtown Annapolis
Oct 18 – 25
Home in Bozman
5.0 out of 5 average rating, 5 reviewsGrace Creek Cottage
May 22 – 29
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