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

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Check availability on Gwynn Hotels with a Pool

Tonight
Oct 13 - Oct 14
Tomorrow
Oct 14 - Oct 15
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 row of beachside cabins with individual porches and windows, each with a door number.
A small house with a 'Welcome' sign on the side, a porch with two chairs, and a white fence in the background.
A long, covered corridor with a green door marked "110" and a window with a view of the landscape.

1. Dockside Inn

Dockside Inn
Deltaville
  • Refreshing poolside stays on the bay with nearby outdoor swimming and free bicycles.
CA $251
CA $276 total
includes taxes & fees
Oct 14 - Oct 15
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 lobby with a reception desk, chairs, a fruit bowl, framed pictures, and a waste bin.

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.
CA $144
CA $161 total
includes taxes & fees
Nov 3 - Nov 4
Hampton Inn Gloucester
A Holiday Inn Express & Suites building with a covered entrance and a brick facade.
A modern office space with a desk, two chairs, a blue sofa, and three framed artworks on the wall.
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.

3. 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.
CA $126
CA $140 total
includes taxes & fees
Nov 11 - Nov 12
Holiday Inn Express Gloucester by IHG
A hotel room with two beds, a desk, a chair, and a television.
A restaurant with multiple tables and chairs, a kitchen area, and a ceiling with recessed lighting.
A hotel gym with treadmills, an elliptical, a stationary bike, and a rack of dumbbells.
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.

4. Quality Inn Kilmarnock

Quality Inn Kilmarnock
Kilmarnock
  • Sunlit poolside escape awaits at this city centre hotel with hydromassage showers.
CA $143
CA $162 total
includes taxes & fees
Nov 11 - Nov 12
Quality Inn Kilmarnock
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a building with a sloped roof.
A modern bathroom with a glass shower enclosure, a walk-in shower, a double sink vanity, and a large mirror.
A restaurant with a boat-shaped counter, wooden ceiling, and large windows.
A hotel room with a large bed, a desk, a chair, a balcony with a view, and a ceiling fan.

5. The Tides Inn

The Tides Inn
Irvington
  • Seaside oasis dazzles with private beach, seasonal pool, and poolside bar perfect for sun-soaked relaxation.
CA $406
CA $508 total
includes taxes & fees
Nov 11 - Nov 12
The Tides Inn
A hammock tied between two trees in a forested area.
A forest clearing with tall trees and a metal container on the ground.
A forest trail with a clear path, surrounded by tall trees and dense underbrush.
A dense forest with snow-covered trees and branches.

6. Campsite #3 At Blanchard Farm

Campsite #3 At Blanchard Farm
Diggs
  • Savour poolside bliss at this rural retreat with a crystal-clear outdoor pool perfect for sun-soaked summer afternoons.
CA $26
CA $60 total
includes taxes & fees
Oct 20 - Oct 21
Campsite #3 At Blanchard Farm
A covered outdoor area with a pool, wicker furniture, and large windows offering a view of the outdoors.
A dining area with a table, chairs, a window with a view of the outdoors, and a framed picture on the wall.
A bedroom with a bed, bedside tables, a window, and a nightstand.
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
CA $322
CA $607 total
includes taxes & fees
Oct 19 - Oct 20
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.
A wooden picnic table with a pitcher, glasses, and a plate set on a grassy area by a body of water.
A room with wicker furniture, a large mirror, and framed pictures on the wall.
A dining room with a wooden table set for six, surrounded by chairs.

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

Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden
Locust Hill
CA $393
CA $789 total
includes taxes & fees
Oct 20 - Oct 21
Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden
A swimming pool with blue chairs, a wooden deck, and large windows.
A modern kitchen with white cabinetry, stainless steel appliances, and a central island.
A large, two-story house with a wrap-around porch, situated near a lake.
A hot tub on a deck with a view of a lake and sunset.

9. 9BR Waterfront Oasis! Pickleball, Hot tub, Sauna & Theater

9BR Waterfront Oasis! Pickleball, Hot tub, Sauna & Theater
North
CA $1,009
CA $2,157 total
includes taxes & fees
Oct 29 - Oct 30
9BR Waterfront Oasis! Pickleball, Hot tub, Sauna & Theater
A swimming pool with a wooden deck and a view of a lake.
A bedroom with a large window, a bed with a floral bedspread, and a view of a lake and trees.
A kitchen with wooden cabinets, a dining area with a table and chairs, and a view of greenery outside.
A house surrounded by dense greenery and a small dock extending into a body of water.

10. Nassawadox Creek Waterfront Home with Private Pool

Nassawadox Creek Waterfront Home with Private Pool
Exmore
CA $276
CA $667 total
includes taxes & fees
Nov 1 - Nov 2
Nassawadox Creek Waterfront Home with Private Pool
View all properties

Choose what matters most at hotels with a pool in Gwynn

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Gwynn Hotel Reviews

Hampton Inn Gloucester

Hampton Inn Gloucester

10/10 Excellent
"Great hotel. Clean and very accommodating"
Ashlie 1-night trip
Posted 20 hours ago
Hampton Inn Gloucester
Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

8/10 Good
"One of the better breakfasts encountered at such places."
David 2-night trip
Posted 6 days ago
Holiday Inn Express Gloucester by IHG
Whispering Pines by Hotel O Whitestone VA

Whispering Pines by Hotel O Whitestone VA

8/10 Good
"Though it is obvious that money is tight and some maintenance and ambiance needs have been put on hold, the staff couldn’t have been more helpful and pleasant. It was a much lower price than other places to stay, and I enjoyed my time there."
Ellen 3-night trip
Posted 3 weeks ago
Whispering Pines by Hotel O Whitestone VA

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.

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