Find Hotels with a Pool in Gwynn, VA

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Gwynn Hotels with a Pool

This weekend
Next weekend

Top Gwynn Hotels with a Pool

Dockside Inn
3.0 star property
  • Pool loungers
  • Near the beach
9.4 out of 10, Exceptional, (42)
Poolside relaxation awaits with umbrellas and attentive lifeguards just steps from this charming bayside retreat. Free bicycle rentals invite coastal exploration, while private yard accommodations offer a tranquil haven after sun-soaked adventures.
The price is AED 514
AED 596 total
includes taxes & fees
4 Nov - 5 Nov
Dockside Inn
Yurt Campsite @ Blanchard Farm Site 2
  • Outdoor pool
10.0 out of 10, Exceptional, (2)
Surrounded by nature, the inviting outdoor pool creates a tranquil escape after exploring the grounds. This yurt campsite balances rustic charm with comfort, offering cozy fireplaces, kitchenettes, and scenic porch views.
The price is AED 275
AED 466 total
includes taxes & fees
4 Nov - 5 Nov
Yurt Campsite @ Blanchard Farm Site 2
The Farm Overlook Treehouse At Blanchard Farm
  • Outdoor pool
10.0 out of 10, Exceptional, (1)
Swimming sessions in the outdoor pool create perfect summer memories at this unique treehouse escape. The cabin features cozy fireplaces, fully equipped kitchenettes, and barbecue facilities for delightful outdoor dining experiences.
The price is AED 312
AED 425 total
includes taxes & fees
4 Nov - 5 Nov
The Farm Overlook Treehouse At Blanchard Farm
Best Western Kilmarnock Hotel
2.5 star property
  • Outdoor pool
7.8 out of 10, Good, (706)
Refreshing waters beckon in this hotel's outdoor pool, providing a perfect spot to cool off after exploring the city. Concierge services, laundry facilities, and friendly staff ensure a comfortable stay, while rooms feature hydromassage showers for continued relaxation.
The price is AED 492
AED 558 total
includes taxes & fees
4 Nov - 5 Nov
Best Western Kilmarnock Hotel
Hampton Inn Gloucester
2.5 star property
  • Indoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (722)
Crystal-clear waters of the indoor pool invite leisurely swims from morning until evening. Fitness enthusiasts appreciate the adjacent exercise center, while the Art Deco surroundings, complimentary breakfast buffet, and attentive staff create a refreshing retreat.
The price is AED 407
AED 453 total
includes taxes & fees
23 Nov - 24 Nov
Hampton Inn Gloucester
Campsite #3 At Blanchard Farm
  • Outdoor pool
Poolside relaxation awaits at this charming campsite where the outdoor swimming pool provides a refreshing escape from summer heat. After a dip, guests can gather around their private firepit under starry skies for an authentic countryside experience.
The price is AED 73
AED 162 total
includes taxes & fees
4 Nov - 5 Nov
Campsite #3 At Blanchard Farm
The Tides Inn
4.0 star property
  • Poolside bar
  • On private beach
  • Full-service spa
8.8 out of 10, Excellent, (159)
Marina views complement refreshing dips in the seasonal outdoor pool at this beachfront haven. Guests savor excellent cuisine at the poolside restaurant while enjoying cocktails from the bar, then unwind with soothing spa treatments.
The price is AED 731
AED 964 total
includes taxes & fees
30 Nov - 1 Dec
The Tides Inn
Holiday Inn Express Gloucester by IHG
3.5 star property
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
7.2 out of 10, Good, (654)
Guests rave about this clean, well-maintained seasonal outdoor pool where some even swim with their dogs. The hotel combines aquatic relaxation with 24-hour fitness options and friendly staff service near historical Gloucester attractions.
The price is AED 386
AED 429 total
includes taxes & fees
3 Dec - 4 Dec
Holiday Inn Express Gloucester by IHG
Yurt Campsite At Blanchard Farm
  • Outdoor pool
Refreshing dips await in the outdoor pool at this countryside yurt campsite. Families appreciate the playground, garden spaces, and cozy fireplaces inside each accommodation, creating an ideal blend of rustic charm and modern comfort.
The price is AED 275
AED 385 total
includes taxes & fees
4 Nov - 5 Nov
Yurt Campsite At Blanchard Farm
Deltaville Serene Riverfront Getaway | 4BR
2.0 star property
  • Pool
  • Kitchen
  • Washer
  • Air conditioning
  • Parking available
  • Barbecue grill
9.8 out of 10, Exceptional, (8)
The price is AED 964
AED 2,560 total
includes taxes & fees
4 Dec - 5 Dec
Deltaville Serene Riverfront Getaway | 4BR
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.

Top Gwynn Hotel Reviews

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations with pools in Gwynn?
Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water: Offers buffet, a seasonal outdoor pool, and free self parking. Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!: Provides a snack bar/deli, an indoor pool, and buffet. Holiday Inn Express Gloucester by IHG: Features full, an outdoor pool, and free self parking. Hampton Inn Gloucester: Provides a private beach, a seasonal outdoor pool, and 2 restaurants. Best Western Kilmarnock Hotel: Offers 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.