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Search results; Over 1,000 homes in Gwynn

Guest favourite
Home in Gwynn
~ Beautiful Gwynn’s Island Waterfront Home ~
4 bedrooms, 6 beds, 2 private bathrooms
1–8 Aug
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5.0 out of 5 average rating, 43 reviews
Top guest favourite
Home in Gwynn
‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 96 reviews
Home in Hudgins
Gwynn's Island Gem | Private Beach & Bay Views
3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Home in Gwynn
Beachfront Oasis
5 bedrooms, 7 beds, 4 bathrooms
12–17 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Gwynn
Mathews Gwynn's Island Chesapeake Bay- Sand Beach!
3 bedrooms, 5 beds, 2 bathrooms
17–22 Aug
4.99 out of 5 average rating, 89 reviews
Guest favourite
Cottage in Gwynn
Sunset Haven
3 bedrooms, 4 beds, 2 bathrooms
18–23 Aug
4.89 out of 5 average rating, 47 reviews
Guest favourite
Home in Gwynn
The Sandbar on Gwynn’s Island
3 bedrooms, 4 beds, 2.5 bathrooms
22–27 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Hudgins
Oyster Haven- private beach front home 3 bedrooms
3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Jul
5.0 out of 5 average rating, 29 reviews
Guest favourite
Cottage in Gwynn
Island Get-A-Way on the Chesapeake Bay with Beach
3 bedrooms, 5 beds, 1 bathroom
16–23 Aug
4.93 out of 5 average rating, 41 reviews
Top guest favourite
Home in Grimstead
Gwynns Island Waterfront Getaway
3 bedrooms, 4 beds, 1 bathroom
11–16 Jul
4.89 out of 5 average rating, 357 reviews
Hotel in Gwynn
Cricket Hill House — Waterfront Suite, 2 East
1 bedroom, 1 king bed, 1 bathroom
5–10 Jul
New place to stay
Guest house in Redart
Tiny Island House
1 bedroom, 1 queen bed, 1 bathroom
18–23 Jul
New place to stay
Guest favourite
Cottage in Gwynn
320 Water View and Access Retreat - Fiddlers Green
2 bedrooms, 4 beds, 2 bathrooms
18–23 Jul
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Home in Mathews County
Oyster Haven on Lanes Creek
2 bedrooms, 2 queen beds, 1 bathroom
27 Jul – 1 Aug
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Home in Gwynn
Island Oasis 4+ acre waterfront house with hot tub
4 bedrooms, 7 beds, 2.5 bathrooms
15–20 Aug
4.98 out of 5 average rating, 46 reviews
Guest favourite
Home in Hudgins
Private Beach Getaway at Finest Chesapeake Bay
3 bedrooms, 7 beds, 2 bathrooms
22–27 Aug
4.96 out of 5 average rating, 28 reviews
Superhost
Home in Cape Charles
Brand new/ Water views/ block to beach!
4 bedrooms, 6 beds, 2.5 bathrooms
6–11 Jul
New place to stay
Guest favourite
Home in Moon
The Retreat at Lilly's Neck
4 bedrooms, 4 beds, 1 bathroom
14–19 Aug
4.92 out of 5 average rating, 66 reviews
Top guest favourite
Flat in Cobbs Creek
Peaceful Private Waterside Apartment
2 bedrooms, 2 queen beds, 1.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 44 reviews