filters

Search results; Over 1,000 homes in Sherwood

Photo 1 of 6
Guest favourite
Home in Sherwood
Punch Point boasts a sandy beach w/ pool and pier
5 bedrooms, 5 beds, 4.5 private bathrooms
13–18 Sept
,
5.0 out of 5 average rating, 21 reviews
Photo 1 of 6
Guest favourite
Home in Sherwood
Paradise Found - Duck Duck Goose on Waterhole Cove
7 bedrooms, 8 beds, 7 bathrooms
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Photo 1 of 6
Guest favourite
Home in Sherwood
Chesapeake Mansion-heated pool 30acre waterfront
8 bedrooms, 11 beds, 11 bathrooms
5–10 Oct
4.99 out of 5 average rating, 79 reviews
Photo 1 of 6
Home in Sherwood
Private Retreat with BIG Water Views!
6 bedrooms, 10 beds, 3 bathrooms
5–10 Sept
4.92 out of 5 average rating, 13 reviews
Photo 1 of 6
Top guest favourite
Home in Sherwood
Time Stands Still, While Memories Are Made.
6 bedrooms, 8 beds, 4.5 bathrooms
13–18 Sept
4.97 out of 5 average rating, 34 reviews
Photo 1 of 6
Top guest favourite
Cottage in Wittman
"Wittman Cottage"
3 bedrooms, 3 beds, 2 bathrooms
27 Oct – 1 Nov
4.9 out of 5 average rating, 198 reviews
Photo 1 of 6
Featured hotel
Room in St. Michaels
Standard double room
2 double beds, 1 bathroom
7–12 Sept
New place to stay
Photo 1 of 6
Top guest favourite
Home in Shady Side
Waterfront Coastal Retreat w/ Beach Access
3 bedrooms, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Photo 1 of 6
Top guest favourite
Home in Tilghman Island
The Getaway
3 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 34 reviews
Photo 1 of 6
Home in Bozman
Brand-New Pool! Waterfront Bozman Village Home
4 bedrooms, 6 beds, 2.5 bathrooms
4–9 Oct
4.81 out of 5 average rating, 16 reviews
Photo 1 of 6
Guest favourite
Home in St. Michaels
Cozy, Family-Friendly Log Cabin-St. Michaels
4 bedrooms, 5 beds, 3 bathrooms
19–24 Sept
5.0 out of 5 average rating, 17 reviews
Photo 1 of 6
Top guest favourite
Home in Stevensville
Bayview Bungalow - Water view, EV charging station
3 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 86 reviews
Photo 1 of 6
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
5 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.96 out of 5 average rating, 79 reviews
Photo 1 of 6
Top guest favourite
Home in St. Michaels
Shipwrights Cottage in Town!
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.99 out of 5 average rating, 173 reviews
Photo 1 of 6
Top guest favourite
Home in Shady Side
A Happy Place
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 30 reviews
Photo 1 of 6
Guest favourite
Cottage in St. Michaels
Cottage #8 Shoreline Retreat Cottage
2 bedrooms, 2 beds, 1 bathroom
26 Sept – 1 Oct
4.85 out of 5 average rating, 34 reviews
Photo 1 of 6
Guest favourite
Home in Deale
Franklin At The Bay
4 bedrooms, 9 beds, 2.5 bathrooms
13–18 Sept
4.85 out of 5 average rating, 26 reviews
Photo 1 of 6
Guest favourite
Home in Wittman
Waterfront cottage in Wittman Maryland
2 bedrooms, 3 beds, 1 bathroom
29 Sept – 4 Oct
4.95 out of 5 average rating, 21 reviews
Photo 1 of 6
Top guest favourite
Home in Oxford
Stunning Chesapeake waterfront home
5 bedrooms, 9 beds, 4.5 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 97 reviews