Find Hotels with a Pool in Gwynn, VA

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Check prices for these dates

Tonight
7 Nov - 8 Nov
Tomorrow
8 Nov - 9 Nov
Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

Our top choices for Gwynn hotels with a pool

A bedroom with a bed, a bedside table, a lamp, a TV, and a window.

1. Dockside Inn

Dockside Inn
3.0 star property
Deltaville
9.4 out of 10, Exceptional, (57 reviews)
  • cleanliness
    Refreshing poolside stays on the bay with nearby outdoor swimming and free bicycles.
The price is AED 703
AED 775 total
includes taxes & fees
15 Nov - 16 Nov
Dockside Inn
An indoor swimming pool with multiple lounge chairs and a tiled floor.

2. Hampton Inn Gloucester

Hampton Inn Gloucester
2.5 star property
Gloucester
9.2 out of 10, Wonderful, (811 reviews)
  • cleanliness
    Dive into refreshing comfort at this hotel with an indoor pool, where aquatic relaxation and sun loungers await all day long.
The price is AED 372
AED 414 total
includes taxes & fees
15 Nov - 16 Nov
Hampton Inn Gloucester
A Holiday Inn Express & Suites building with a covered entrance and a brick facade.

3. Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG
3.5 star property
Gloucester
7.2 out of 10, Good, (759 reviews)
  • cleanliness
    Dive into summer splashing at this refreshing seasonal outdoor pool, perfect for cooling off during hot Virginia days.
The price is AED 312
AED 347 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Gloucester by IHG
A hotel room with two beds, a desk, a chair, and a television.

4. Quality Inn Kilmarnock

Quality Inn Kilmarnock
2.5 star property
Kilmarnock
7.6 out of 10, Good, (795 reviews)
  • cleanliness
    Sunlit poolside escape awaits at this city center hotel with hydromassage showers.
The price is AED 380
AED 431 total
includes taxes & fees
12 Nov - 13 Nov
Quality Inn Kilmarnock
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a building with a sloped roof.

5. The Tides Inn

The Tides Inn
4.0 star property
Irvington
9.0 out of 10, Wonderful, (187 reviews)
  • cleanliness
    Seaside oasis dazzles with private beach, seasonal pool, and poolside bar perfect for sun-soaked relaxation.
The price is AED 915
AED 1,165 total
includes taxes & fees
29 Nov - 30 Nov
The Tides Inn
A forest trail with a clear path, surrounded by tall trees and dense underbrush.

6. Campsite #3 At Blanchard Farm

Campsite #3 At Blanchard Farm
Diggs
  • cleanliness
    Savor poolside bliss at this rural retreat with a crystal-clear outdoor pool perfect for sun-soaked summer afternoons.
The price is AED 66
AED 122 total
includes taxes & fees
14 Nov - 15 Nov
Campsite #3 At Blanchard Farm
A covered outdoor area with a pool, wicker furniture, and large windows offering a view of the outdoors.

7. The Bungalow, Pool, Dock, Kayaks, & Game Room

The Bungalow, Pool, Dock, Kayaks, & Game Room
Topping
The price is AED 617
AED 1,224 total
includes taxes & fees
8 Nov - 9 Nov
The Bungalow, Pool, Dock, Kayaks, & Game Room
A swimming pool with a tiled edge, surrounded by a patio area with white metal chairs and a table.

8. Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden

Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden
Locust Hill
10.0 out of 10, Exceptional, (41 reviews)
The price is AED 984
AED 1,888 total
includes taxes & fees
8 Nov - 9 Nov
Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden
A swimming pool with a wooden deck and a view of a lake.

9. Nassawadox Creek Waterfront Home with Private Pool

Nassawadox Creek Waterfront Home with Private Pool
Exmore
10.0 out of 10, Exceptional, (79 reviews)
The price is AED 661
AED 1,578 total
includes taxes & fees
1 Dec - 2 Dec
Nassawadox Creek Waterfront Home with Private Pool
A covered patio with a pool, outdoor furniture, and a view of the ocean.

10. Waterfront Home with pool, dock, gameroom, and kayaks!

Waterfront Home with pool, dock, gameroom, and kayaks!
Topping
10.0 out of 10, Exceptional, (1 review)
The price is AED 2,468
AED 4,091 total
includes taxes & fees
21 Nov - 22 Nov
Waterfront Home with pool, dock, gameroom, and kayaks!
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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Choose what matters most at hotels with a pool in Gwynn

Breakfast included
4 stars

Top Gwynn Hotel Reviews

An indoor swimming pool with multiple lounge chairs and a tiled floor.
Hampton Inn Gloucester

Hampton Inn Gloucester

Hampton Inn Gloucester
Gloucester

10/10 Excellent

Fantastic
United States
Joseph
Reviewed July 31, 2025
Hampton Inn Gloucester

Frequently Asked Questions

What are some accommodations with pools in Gwynn?

Waterfront Cottage w Private Beach on Chesapeake Bay!: Offers a private beach, a seasonal outdoor pool, and 2 restaurants. Gwynn's Island Gem | Private Beach & Bay Views: Provides a snack bar/deli, an indoor pool, and buffet. The Tides Inn: Features full, an outdoor pool, and free self parking. Hampton Inn Gloucester: Offers buffet, a seasonal outdoor pool, and free self parking. Quality Inn Kilmarnock: Features 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 Museum 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.