Beachfront holiday rentals in Gwynn Island
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Top-rated beachfront rentals in Gwynn Island
Guests agree: these beachfront homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for beachfront rentals in Gwynn Island
Pet-friendly beachfront home rentals
Home in Cape Charles
4.95 out of 5 average rating, 119 reviewsHarbor View- (Sun - Sun rental June- Sept)
18–25 Jan
Cottage in Gwynn
4.96 out of 5 average rating, 26 reviewsIsland Get-A-Way on the Chesapeake Bay with Beach
13–20 Oct
Home in Moon
5.0 out of 5 average rating, 15 reviewsThe Retreat at Lilly's Neck
4–11 Oct
Home in Deltaville
4.96 out of 5 average rating, 28 reviewsSunset Pointe
12–19 Nov
Home in White Stone
5.0 out of 5 average rating, 50 reviewsOyster Creek Retreat: Waterfront | Dock | 2 Kings
16–23 Jan
Home in Hampton
4.98 out of 5 average rating, 48 reviewsExclusive Beachfront Home w/ 180° Views & Hot Tub!
26 Sep – 3 Oct
Cottage in White Stone
4.97 out of 5 average rating, 77 reviewsLoveShack Cottage
10–17 May
Home in White Stone
5.0 out of 5 average rating, 24 reviewsWaterfront Retreat w/ Hot Tub, Game Room, Kayaks,
19–26 Jan
Beachfront home rentals with a pool
Flat in Cape Charles
4.98 out of 5 average rating, 183 reviewsCape Charles Plantation Home “Nevill’s Nook Suite”
22–29 Dec
Campervan/Motorhome in White Stone
4.9 out of 5 average rating, 86 reviews“Old Smokey”A cozy, single bedroom, unique getaway
4–11 Dec
Barn in Cobbs Creek
4.95 out of 5 average rating, 94 reviewsThe Barn at Pond Point - Riverfront Home
28 Sep – 5 Oct
Home in Heathsville
4.92 out of 5 average rating, 25 reviewsWeekly discount 10% - cottage with pool and dock!
12–19 Nov
Holiday home in Cape Charles
5.0 out of 5 average rating, 15 reviewsCheerful 3 bedroom Beach House in Cape Charles, VA
30 Sep – 7 Oct
Home in Cape Charles
5.0 out of 5 average rating, 8 reviewsCoastal Soul/spacious/updated/perfect beach escape
12–19 May
Cabin in White Stone
4.85 out of 5 average rating, 113 reviewsTwo Bedroom + Loft Cabin on the Bay
12–19 Jul
Home in Cape Charles
5.0 out of 5 average rating, 3 reviewsHandicap Accesible, with Beach, Pool & Tennis!
27 Dec – 3 Jan
Private beachfront home rentals
Home in North
5.0 out of 5 average rating, 40 reviewsThe Llama House
18–25 Mar
Home in Gwynn
4.98 out of 5 average rating, 61 reviews‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi
8–15 Apr
Treehouse in Machipongo
4.96 out of 5 average rating, 25 reviewsTreehouse Couple's Retreat
30 Jan – 6 Feb
Home in Cobbs Creek
4.98 out of 5 average rating, 45 reviewsThe Gold Coast
26 Feb – 5 Mar
Cottage in Deltaville
5.0 out of 5 average rating, 64 reviewsUnique & bright two-bedroom waterfront cottage
15–22 Feb
Place to stay in Machipongo
5.0 out of 5 average rating, 54 reviewsSmokehouse on the Chesapeake Bay
18–25 Sep
Home in Machipongo
5.0 out of 5 average rating, 33 reviewsPrivate Country Beach Retreat
23–30 Dec
Guest suite in Cape Charles
5.0 out of 5 average rating, 34 reviewsChesapeake Retreat - Bay view
11–18 Oct
Destinations to explore
- Virginia Beach Holiday rentals
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