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Search results; Over 1,000 homes in Gwynn

Top guest favourite
Cottage in Gwynn
320 Water View and Access Retreat - Fiddlers Green
2 bedrooms, 4 beds, 2 private bathrooms
18–23 Jul
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4.92 out of 5 average rating, 13 reviews
Hotel in Gwynn
Cricket Hill House — Waterfront Suite, 2 East
New place to stay, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Home in Gwynn
‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi
4.98 out of 5 average rating, 96 reviews, 3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Home in Gwynn
Mathews Gwynn's Island Chesapeake Bay- Sand Beach!
4.99 out of 5 average rating, 90 reviews, 3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Home in Gwynn
Beachfront Oasis
5.0 out of 5 average rating, 12 reviews, 5 bedrooms, 7 beds, 4 bathrooms
23–28 Aug
Top guest favourite
Home in Hudgins
Oyster Haven- private beach front home 3 bedrooms
5.0 out of 5 average rating, 30 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Jul
Guest house in Redart
Tiny Island House
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Aug
Home in Hudgins
Gwynn's Island Gem | Private Beach & Bay Views
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
Guest favourite
Cottage in Gwynn
Sunset Haven
4.9 out of 5 average rating, 48 reviews, 3 bedrooms, 4 beds, 2 bathrooms
18–23 Aug
Guest favourite
Cottage in Gwynn
Island Get-A-Way on the Chesapeake Bay with Beach
4.93 out of 5 average rating, 41 reviews, 3 bedrooms, 5 beds, 1 bathroom
16–23 Aug
Guest favourite
Home in Gwynn
The Sandbar on Gwynn’s Island
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Home in Grimstead
Gwynns Island Waterfront Getaway
4.89 out of 5 average rating, 357 reviews, 3 bedrooms, 4 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Gwynn
Island Oasis 4+ acre waterfront house with hot tub
4.98 out of 5 average rating, 46 reviews, 4 bedrooms, 7 beds, 2.5 bathrooms
15–20 Aug
Top guest favourite
Home in Mathews County
Oyster Haven on Lanes Creek
4.94 out of 5 average rating, 16 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Home in Mathews
Garden Cottage in Downtown Mathews
4.99 out of 5 average rating, 126 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Guest favourite
Home in Hudgins
Private Beach Getaway at Finest Chesapeake Bay
4.97 out of 5 average rating, 30 reviews, 3 bedrooms, 7 beds, 2 bathrooms
22–27 Aug
Guest favourite
Home in Gwynn
~ Beautiful Gwynn’s Island Waterfront Home ~
5.0 out of 5 average rating, 43 reviews, 4 bedrooms, 6 beds, 2 bathrooms
1–8 Aug
Superhost
Home in Mathews County
Island Vibes/ Bayfront Retreat w/private beach
New place to stay, 3 bedrooms, 3 beds, 3 bathrooms
3–8 Aug
Superhost
Home in Bavon
Chesapeake Shore Cottage: Private Beach w/Kayaks
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 3 beds, 2 bathrooms
24–29 Aug