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Search results; Over 1,000 homes in Gwynn

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Guest favourite
Home in Gwynn
~ Beautiful Gwynn’s Island Waterfront Home ~
4 bedrooms, 6 beds, 2 private bathrooms
1–6 Oct
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5.0 out of 5 average rating, 47 reviews
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Top guest favourite
Home in Gwynn
‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi
3 bedrooms, 5 beds, 2 bathrooms
11–16 Oct
4.98 out of 5 average rating, 103 reviews
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Top guest favourite
Hotel in Gwynn
Cricket Hill House — Waterfront Suite, 2 East
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 9 reviews
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Guest favourite
Cottage in Gwynn
Sunset Haven
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.9 out of 5 average rating, 52 reviews
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Top guest favourite
Home in Grimstead
Gwynns Island Waterfront Getaway
3 bedrooms, 4 beds, 1 bathroom
10–15 Oct
4.89 out of 5 average rating, 369 reviews
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Cottage in Gwynn
Island Get-A-Way on the Chesapeake Bay with Beach
3 bedrooms, 5 beds, 1 bathroom
4–11 Oct
4.93 out of 5 average rating, 43 reviews
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Top guest favourite
Guest house in Redart
Tiny Island House
1 bedroom, 1 queen bed, WC
12–17 Oct
4.94 out of 5 average rating, 17 reviews
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Top guest favourite
Home in Gwynn
Beachfront Oasis
5 bedrooms, 7 beds, 4 bathrooms
1–6 Oct
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Home in Hudgins
Oyster Haven- private beach front home 3 bedrooms
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 40 reviews
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Top guest favourite
Home in Gwynn
Mathews Gwynn's Island Chesapeake Bay- Sand Beach!
3 bedrooms, 5 beds, 2 bathrooms
13–18 Oct
4.99 out of 5 average rating, 96 reviews
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Guest favourite
Home in Gwynn
The Sandbar on Gwynn’s Island
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 14 reviews
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Home in Hudgins
Gwynn's Island Gem | Private Beach & Bay Views
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 5 reviews
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Home in Hallieford
Cozy getaway down by the Bay "GreenBay"
3 bedrooms, 3 beds, 2 bathrooms
27 Oct – 1 Nov
New place to stay
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Top guest favourite
Home in Cobbs Creek
Blue Heron WaterSide
4 bedrooms, 8 beds, 2 bathrooms
12–17 Oct
4.98 out of 5 average rating, 176 reviews
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Superhost
Cottage in Deltaville
Stunning Beachfront Cottage on the Chesapeake
4 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.77 out of 5 average rating, 168 reviews
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Top guest favourite
Cottage in Gwynn
320 Water View and Access Retreat - Fiddlers Green
2 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.95 out of 5 average rating, 20 reviews
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Top guest favourite
Home in Gwynn
Island Oasis 4+ acre waterfront house with hot tub
4 bedrooms, 7 beds, 2.5 bathrooms
1–6 Oct
4.98 out of 5 average rating, 49 reviews
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Top guest favourite
Cabin in Deltaville
"The Little Red Cabin" aka The Galley
1 bedroom, 2 beds, 1 bathroom
29 Oct – 3 Nov
4.97 out of 5 average rating, 354 reviews
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Top guest favourite
Home in Cobbs Creek
Million $ Views! Pool! Private Hot Tub! EV Charger
3 bedrooms, 4 beds, 1 bathroom
15–20 Nov
4.91 out of 5 average rating, 183 reviews