Find Hotels with a Pool in Gwynn, VA

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Check availability on Gwynn Hotels with a Pool

Our top choices for Gwynn hotels with a pool

Traditional Room | Free WiFi
Dockside Inn

Dockside Inn

3.0 star property
Deltaville
9.4 out of 10, Exceptional, (44)
"Great stay"
United States
Cynthia
$145 nightly
The price is $160
Dec 10 - Dec 11
Total with taxes and fees
Dockside Inn
Outdoor pool
The Farm Overlook Treehouse At Blanchard Farm

The Farm Overlook Treehouse At Blanchard Farm

Diggs
10.0 out of 10, Exceptional, (1)
$105 nightly
The price is $116
Dec 10 - Dec 11
Total with taxes and fees
The Farm Overlook Treehouse At Blanchard Farm
Indoor pool, open 10 AM to 10 PM, sun loungers
Hampton Inn Gloucester

Hampton Inn Gloucester

2.5 star property
Gloucester
9.2 out of 10, Wonderful, (731)
"Will stay again. "
United States
Jennifer
$95 nightly
The price is $106
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn Gloucester
Outdoor pool
Yurt Campsite @ Blanchard Farm Site 2

Yurt Campsite @ Blanchard Farm Site 2

Diggs
10.0 out of 10, Exceptional, (2)
"This is a fabulous yurt stay! 3 minute drive to the beach/ bay! Very nice just with a full farm! Great for kids! "
United States
Colleen C.
$115 nightly
The price is $127
Dec 10 - Dec 11
Total with taxes and fees
Yurt Campsite @ Blanchard Farm Site 2
Outdoor pool
Best Western Kilmarnock Hotel

Best Western Kilmarnock Hotel

2.5 star property
Kilmarnock
7.6 out of 10, Good, (721)
"Friendly staff, clean property "
United States
etta
$119 nightly
The price is $135
Dec 10 - Dec 11
Total with taxes and fees
Best Western Kilmarnock Hotel
Free daily buffet breakfast
Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

3.5 star property
Gloucester
7.2 out of 10, Good, (662)
"Clean room staff all good"
United States
George
$91 nightly
The price is $101
Dec 15 - Dec 16
Total with taxes and fees
Holiday Inn Express Gloucester by IHG
Property grounds
Campsite #3 At Blanchard Farm

Campsite #3 At Blanchard Farm

Diggs
$40 nightly
The price is $44
Jan 4 - Jan 5, 2026
Total with taxes and fees
Campsite #3 At Blanchard Farm
Outdoor pool
Yurt Campsite At Blanchard Farm

Yurt Campsite At Blanchard Farm

Diggs
$95 nightly
The price is $105
Dec 10 - Dec 11
Total with taxes and fees
Yurt Campsite At Blanchard Farm
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Gwynn Hotel Reviews

Hampton Inn Gloucester

Hampton Inn Gloucester

10/10 Excellent
"The hotel was clean and nicely decorated. Staff was attentive and courteous. "
David 4-night trip
Posted 9 days ago
Hampton Inn Gloucester

Frequently asked questions

What are some accommodations with pools in Gwynn?
Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water: Features buffet, a seasonal outdoor pool, and free self parking. Holiday Inn Express Gloucester by IHG: Offers a snack bar/deli, an indoor pool, and buffet. Hampton Inn Gloucester: Provides full, an outdoor pool, and free self parking. Best Western Kilmarnock Hotel: Offers a private beach, a seasonal outdoor pool, and 2 restaurants. Warner Hall: Provides a private beach, a seasonal outdoor pool, and free water-park access.
What is there to see and do in Gwynn?
Spend some time experiencing the great outdoors at Chesapeake Bay. Discover sights such as Gwynn's Island Musuem during your stay.
When is the best time to book a hotel with a pool in Gwynn?
You may want to consider an accommodation that has an outdoor pool if you will be visiting Gwynn in the hottest months of July, August, or June when the average temp is 76°F. Lodging with an indoor pool may be what you want if you come to town during the coldest months of January, February, or December when the average temperature is 44°F.

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