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Search results; Over 1,000 homes in Gwynn

Descriptions are based on details hosts provide
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
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
Top guest favourite
Home in Gwynn
Beachfront on the Chesapeake with kayaks
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
Guest house in Redart
Tiny Island House
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Jul
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
Home in Gwynn
Private sandy beach on Chesapeake Bay
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 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
Home in Hudgins
Gwynn's Island Gem | Private Beach & Bay Views
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Cabin in Deltaville
"The Little Red Cabin" aka The Galley
4.97 out of 5 average rating, 344 reviews, 1 bedroom, 2 beds, 1 bathroom
20–25 Sept
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
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
Tiny home in Diggs
Off-grid cabin with a clear roof
4.95 out of 5 average rating, 228 reviews, 1 bedroom, 3 beds, 1 bathroom
27 Jul – 1 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 Mathews
Hot tub and fire pit on Main Street
4.99 out of 5 average rating, 126 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Superhost
Home in Gloucester County
Waterfront cottage with a private dock
3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Tiny home in North
Luxury tiny home on 3 wooded acres
5.0 out of 5 average rating, 8 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug