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Search results; Over 1,000 homes in Gwynn

Top guest favourite
Home in Gwynn
‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi
3 bedrooms, 5 beds, 2 private bathrooms
20–25 Sept
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4.98 out of 5 average rating, 98 reviews
Room in Gwynn
Cricket Hill House — Waterfront Suite, 2 East
1 king bed
1–6 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Gwynn
Beachfront Oasis
5 bedrooms, 7 beds
23–28 Aug
5.0 out of 5 average rating, 13 reviews
Home in Hudgins
Gwynn's Island Gem | Private Beach & Bay Views
3 bedrooms, 4 beds
17–22 Aug
Top guest favourite
Home in Gwynn
Mathews Gwynn's Island Chesapeake Bay- Sand Beach!
3 bedrooms, 5 beds
20–25 Sept
4.99 out of 5 average rating, 90 reviews
Guest favourite
Cottage in Gwynn
Sunset Haven
3 bedrooms, 4 beds
24–29 Aug
4.9 out of 5 average rating, 49 reviews
Guest favourite
Home in Hudgins
Private Beach Getaway at Finest Chesapeake Bay
3 bedrooms, 7 beds
22–27 Aug
4.97 out of 5 average rating, 31 reviews
Guest favourite
Guest house in Redart
Tiny Island House
1 bedroom, 1 queen bed
24–29 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Hudgins
Oyster Haven- private beach front home 3 bedrooms
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Gwynn
The Sandbar on Gwynn’s Island
3 bedrooms, 4 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Gwynn
Island Oasis 4+ acre waterfront house with hot tub
4 bedrooms, 7 beds
15–20 Aug
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Home in Grimstead
Gwynns Island Waterfront Getaway
3 bedrooms, 4 beds
9–14 Aug
4.89 out of 5 average rating, 358 reviews
Guest favourite
Cottage in Gwynn
Island Get-A-Way on the Chesapeake Bay with Beach
3 bedrooms, 5 beds
23–30 Aug
4.93 out of 5 average rating, 41 reviews
Guest favourite
Home in Gwynn
~ Beautiful Gwynn’s Island Waterfront Home ~
4 bedrooms, 6 beds
8–15 Aug
5.0 out of 5 average rating, 43 reviews
Cottage in Reedville
The Beach Next Door
3 bedrooms, 3 beds
23–28 Aug
New place to stay
Top guest favourite
Home in Mathews
Garden Cottage in Downtown Mathews
1 bedroom, 1 king bed
30 Aug – 4 Sept
4.99 out of 5 average rating, 127 reviews
Superhost
Home in Deltaville
Creekwood Waterfront Retreat on Hunton Creek
3 bedrooms, 5 beds
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in North
Salt & Pine in Mathews, VA
2 bedrooms
9–14 Aug
5.0 out of 5 average rating, 44 reviews
Top guest favourite
Cottage in Gwynn
320 Water View and Access Retreat - Fiddlers Green
2 bedrooms, 4 beds
1–6 Aug
4.93 out of 5 average rating, 15 reviews