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Search results; Over 1,000 homes in Sherwood

Top guest favourite
Home in Sherwood
Time Stands Still, While Memories Are Made.
6 bedrooms, 8 beds, 4.5 private bathrooms
4–9 Oct
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4.97 out of 5 average rating, 35 reviews
Guest favourite
Home in Sherwood
Paradise Found - Duck Duck Goose on Waterhole Cove
7 bedrooms, 8 beds, 7 bathrooms
15–20 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Sherwood
Punch Point boasts a sandy beach w/ pool and pier
5 bedrooms, 5 beds, 4.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 24 reviews
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, 80 reviews
Home in Sherwood
Private Retreat with BIG Water Views!
6 bedrooms, 10 beds, 3 bathrooms
22–27 Sept
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Cottage in Wittman
"Wittman Cottage"
3 bedrooms, 3 beds, 2 bathrooms
22–27 Nov
4.9 out of 5 average rating, 199 reviews
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, 18 reviews
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
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, 98 reviews
Top guest favourite
Home in Easton
Newly Renovated Modern Waterfront Home
5 bedrooms, 13 beds, 5.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Stevensville
Wildbluesea Retreat
4 bedrooms, 6 beds, 3.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 50 reviews
Guest favourite
Home in Shady Side
Waterfront Coastal Retreat w/ Beach Access
3 bedrooms, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 13 reviews
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
Top guest favourite
Home in Stevensville
Bayview Bungalow - Water view, EV charging station
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Home in St. Michaels
Grace Cottage, Saint Michaels Walk to everything!
2 bedrooms, 2 king beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in St. Michaels
Ahoy St. Michaels! - A Historic Retreat
2 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Cottage in St. Michaels
The Little Anchor Cottage, St. Michaels, MD
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 303 reviews
Guest favourite
Cottage in St. Michaels
Cottage #8 Shoreline Retreat Cottage
2 bedrooms, 2 beds, 1 bathroom
23–28 Sept
4.85 out of 5 average rating, 34 reviews
Top guest favourite
Home in Shady Side
Waterfront Sanctuary only 50 Min. From DC/Balt.
5 bedrooms, 12 beds, 4 bathrooms
29 Sept – 4 Oct
4.97 out of 5 average rating, 112 reviews