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Search results; Over 1,000 homes in Sherwood

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Guest favourite
Home in Sherwood
Punch Point boasts a sandy beach w/ pool and pier
5 bedrooms, 5 beds, 4.5 private bathrooms
1–6 Oct
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5.0 out of 5 average rating, 26 reviews
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Guest favourite
Home in Sherwood
Paradise Found - Duck Duck Goose on Waterhole Cove
7 bedrooms, 8 beds, 7 bathrooms
1–6 Oct
5.0 out of 5 average rating, 7 reviews
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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, 81 reviews
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Top guest favourite
Home in Sherwood
Time Stands Still, While Memories Are Made.
6 bedrooms, 8 beds, 4.5 bathrooms
4–9 Oct
4.97 out of 5 average rating, 35 reviews
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Home in Sherwood
Private Retreat with BIG Water Views!
6 bedrooms, 10 beds, 3 bathrooms
1–6 Oct
4.92 out of 5 average rating, 13 reviews
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Featured hotel
Hotel in St. Michaels
St. Michaels Inn, Standard double room
1 bedroom, 2 double beds, 1 bathroom
4–9 Oct
New place to stay
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Top guest favourite
Home in Tilghman Island
The Getaway
3 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 36 reviews
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Home in Bozman
Brand-New Pool! Waterfront Bozman Village Home
4 bedrooms, 6 beds, 2.5 bathrooms
4–9 Oct
4.82 out of 5 average rating, 17 reviews
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Guest favourite
Home in Royal Oak
Waterfront Farmhouse Retreat on 18 Acres, Pool
8 bedrooms, 10 beds, 7.5 bathrooms
7–12 Oct
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Home in Tilghman Island
Pet-Friendly Summer Retreat on Tilghman
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.76 out of 5 average rating, 17 reviews
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Top guest favourite
Cottage in Wittman
"Wittman Cottage"
3 bedrooms, 3 beds, 2 bathrooms
22–27 Nov
4.9 out of 5 average rating, 200 reviews
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Top guest favourite
Home in Shady Side
Waterfront Coastal Retreat w/ Beach Access
3 bedrooms, 1 bathroom
4–9 Nov
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Home in Wittman
Waterfront cottage in Wittman Maryland
2 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.96 out of 5 average rating, 24 reviews
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Flat in Annapolis
Annapolis Getaway | 2BR Sleeps 6 | Near USNA
3 bedrooms, 2 beds, 2 bathrooms
1–6 Oct
New place to stay
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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
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Top guest favourite
Home in Stevensville
*Waterfront* 5BR w/ Pool + Firepit on Kent Island!
5 bedrooms, 8 beds, 3.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 23 reviews
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Guest favourite
Home in Easton
Waterfront Estate - Riverslie on the Miles River
5 bedrooms, 6 beds, 4 bathrooms
1–6 Oct
4.81 out of 5 average rating, 31 reviews
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Guest favourite
Cottage in St. Michaels
Cottage #8 Shoreline Retreat Cottage
2 bedrooms, 2 beds, 1 bathroom
12–17 Oct
4.85 out of 5 average rating, 34 reviews
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Guest favourite
Home in St. Michaels
St. Michaels Waterfront Retreat | Pet Friendly
3 bedrooms, 4 beds, 3.5 bathrooms
1–6 Oct
4.86 out of 5 average rating, 22 reviews