A pier extending into calm waters at sunset with a clear sky.

Find Hotels with a Pool in Gwynn, VA

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Check availability on Gwynn Hotels with a Pool

Tonight
Aug 22 - Aug 23
Tomorrow
Aug 23 - Aug 24
Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6

Our top choices for Gwynn hotels with a pool

A bedroom with a bed, a bedside table, a lamp, a TV, and a window.
A small house with a 'Welcome' sign on the side, a porch with two chairs, and a white fence in the background.
A room with a coffee machine, two chairs, a sofa, and a view of a dock and trees.
A row of beachside cabins with individual porches and windows, each with a door number.

1. Dockside Inn

Dockside Inn
Deltaville
  • Refreshing poolside stays on the bay with nearby outdoor swimming and free bicycles.
$165 nightly
$182 total
Aug 23 - Aug 24
Total with taxes and fees
Dockside Inn
An indoor swimming pool with clear water, lounge chairs, and potted plants.
A compact hotel room with a kitchenette, a sink, a microwave, and a small dining area with a chair and a table.
A compact hotel room with a kitchenette, a dining area, a TV, and a sofa.
A hotel room with two beds, a nightstand with a lamp, a dresser, and a TV.

2. Hampton Inn Gloucester

Hampton Inn Gloucester
Gloucester
  • Dive into refreshing comfort at this hotel with an indoor pool, where aquatic relaxation and sun loungers await all day long.
$97 nightly
$108 total
Sep 1 - Sep 2
Total with taxes and fees
Hampton Inn Gloucester
A hotel room with two beds, a desk, a chair, and a television.
A hotel reception area with a counter, a sign reading 'Quality by Chuck Hotel,' a reception desk, a blue wall, and a hallway leading to other rooms.
A living room with a fireplace, a television, and two sofas.
A restaurant with multiple tables and chairs, a kitchen area, and a ceiling with recessed lighting.

3. Quality Inn Kilmarnock

Quality Inn Kilmarnock
Kilmarnock
  • Sunlit poolside escape awaits at this city center hotel with hydromassage showers.
$100 nightly
$113 total
Sep 20 - Sep 21
Total with taxes and fees
Quality Inn Kilmarnock
A Holiday Inn Express & Suites building with a covered entrance and a brick facade.
A modern breakfast area with labeled dispensers for yogurt, eggs, and milk.
A reception area with a modern design, featuring a blue geometric wall, a clock, and a reception desk.
A conference room with a long table, blue chairs, framed artwork on the walls, and a large screen displaying the Holiday Inn Express logo.

4. Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG
Gloucester
  • Dive into summer splashing at this refreshing seasonal outdoor pool, perfect for cooling off during hot Virginia days.
$89 nightly
$99 total
Sep 20 - Sep 21
Total with taxes and fees
Holiday Inn Express Gloucester by IHG
A hammock tied between two trees in a forested area.
A dense forest with snow-covered trees and branches.
A forest trail with a clear path, surrounded by tall trees and dense underbrush.
A forest clearing with tall trees and a metal container on the ground.

5. Campsite #3 At Blanchard Farm

Campsite #3 At Blanchard Farm
Diggs
  • Savor poolside bliss at this rural retreat with a crystal-clear outdoor pool perfect for sun-soaked summer afternoons.
$38 nightly
$42 total
Aug 23 - Aug 24
Total with taxes and fees
Campsite #3 At Blanchard Farm
A restaurant with a boat-shaped counter, wooden ceiling, and large windows.
A balcony with two chairs and a table, overlooking a river with boats and houses in the background.

6. The Tides Inn

The Tides Inn
Irvington
  • Seaside oasis dazzles with private beach, seasonal pool, and poolside bar perfect for sun-soaked relaxation.
$389 nightly
$421 total
Aug 24 - Aug 25
Total with taxes and fees
The Tides Inn
A covered outdoor area with a pool, wicker furniture, and large windows offering a view of the outdoors.
A bedroom with a bed, bedside tables, a window, and a nightstand.
A covered outdoor seating area with a view of a pool and lake.
A spacious living room with a television, seating area, and a view of the ocean.

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

The Bungalow, Pool, Dock, Kayaks, & Game Room
Topping
$464 nightly
$512 total
Aug 23 - Aug 24
Total with taxes and fees
The Bungalow, Pool, Dock, Kayaks, & Game Room
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Choose what matters most at hotels with a pool in Gwynn

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Gwynn Hotel Reviews

Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

10/10 Excellent
"No complaints. Staff was great. Breakfast was great. Great location for our needs."
MELANIE 1-night trip
Posted 11 hours ago
Holiday Inn Express Gloucester by IHG
The Tides Inn

The Tides Inn

10/10 Excellent
"The staff was attentive and very helpful."
Heidi 2-night trip
Posted 9 days ago
The Tides Inn
Whispering Pines by Hotel O Whitestone VA

Whispering Pines by Hotel O Whitestone VA

8/10 Good
"It's not the Ritz Csrlton, but it's clean, friendly staff, comfortable bed, and inexpensive. It was a safe place for me and quiet. They had a little problem with my check out. They thought it was one day earlier but I went to the office and they assured me it's was their mistake. They were very good about it and apologized. Overall I only stayed there to sleep and enjoyed my time there 😊 😃 😀"
David 5-night trip
Posted 11 days ago
Whispering Pines by Hotel O Whitestone VA

Frequently asked questions

What are some accommodations with pools in Gwynn?
Gwynn's Island Gem | Private Beach & Bay Views: Provides buffet, a seasonal outdoor pool, and free self parking. Waterfront Cottage w Private Beach on Chesapeake Bay!: Features a private beach, a seasonal outdoor pool, and 2 restaurants. Holiday Inn Express Gloucester by IHG: Offers full, an outdoor pool, and free self parking. The Tides Inn: Features a snack bar/deli, an indoor pool, and buffet. 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.

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