Find Hotels with a Pool in Upperville, VA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Upperville Hotels with a Pool

Next weekend
Jun 5 - Jun 7
In two weeks
Jun 12 - Jun 14

Our top choices for Upperville hotels with a pool

Indoor pool

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (2,267 reviews)
  • cleanliness
    Dive into the inviting indoor pool, perfect for year-round swims at this clean, modern hotel.
The price is ₩183,545
₩199,697 total
includes taxes & fees
May 31 - Jun 1
La Quinta Inn & Suites by Wyndham Winchester
Seasonal outdoor pool

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
Winchester
9.2 out of 10, Wonderful, (895 reviews)
  • cleanliness
    Splash into summer with panoramic mountain views from this seasonal outdoor pool experience.
The price is ₩160,430
₩181,766 total
includes taxes & fees
Jun 10 - Jun 11
Hampton Inn Winchester N/Conference Center, VA
Indoor pool

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town
2.5 star property
Harpers Ferry
7.8 out of 10, Good, (1,001 reviews)
  • cleanliness
    Scenic indoor pool provides year-round escape for travelers seeking relaxation after park adventures.
The price is ₩153,080
₩171,450 total
includes taxes & fees
Jun 21 - Jun 22
Clarion Inn Harpers Ferry - Charles Town
Indoor pool

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,457 reviews)
  • cleanliness
    Make a splash at this Winchester hotel with an indoor pool and fitness center for all seasons.
The price is ₩145,783
₩158,616 total
includes taxes & fees
Jun 2 - Jun 3
Microtel Inn & Suites by Wyndham Winchester
Indoor pool

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (868 reviews)
  • cleanliness
    Splash into Winchester luxury with an indoor pool retreat in a historical Art Deco hotel.
The price is ₩139,389
₩151,655 total
includes taxes & fees
Jun 14 - Jun 15
Fairfield Inn & Suites by Marriott Winchester
Indoor pool

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (897 reviews)
  • cleanliness
    Splash into fun at this pet-friendly hotel with a pristine indoor pool and health club.
The price is ₩162,408
₩176,701 total
includes taxes & fees
Jun 30 - Jul 1
TRU By Hilton Winchester
Lobby

Baymont by Wyndham Warrenton

Baymont by Wyndham Warrenton
2.5 star property
Warrenton
6.4 out of 10, (1,001 reviews)
  • cleanliness
    Splash into summer at this Warrenton motel featuring a seasonal outdoor pool and 24-hour fitness center.
The price is ₩115,002
₩123,397 total
includes taxes & fees
Jun 17 - Jun 18
Baymont by Wyndham Warrenton
Indoor pool

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (986 reviews)
  • cleanliness
    Experience refreshing swims any season at this indoor pool hotel with comfy beds and onsite dining.
The price is ₩160,978
₩175,144 total
includes taxes & fees
Jun 16 - Jun 17
Courtyard by Marriott Winchester
Seasonal outdoor pool

Carradoc Hall Hotel & Conference Center by The Red Collection

Carradoc Hall Hotel & Conference Center by The Red Collection
2.5 star property
Leesburg
6.6 out of 10, (1,000 reviews)
  • cleanliness
    Dive into summer sunshine at this hotel's seasonal outdoor pool, perfect for refreshing vacation memories.
The price is ₩131,426
₩151,139 total
includes taxes & fees
May 31 - Jun 1
Carradoc Hall Hotel & Conference Center by The Red Collection
Indoor pool

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Splash into a year-round swimming oasis with a refreshing indoor pool sanctuary at this Winchester hotel.
The price is ₩140,818
₩153,210 total
includes taxes & fees
Jun 21 - Jun 22
Country Inn & Suites by Radisson, Winchester, VA
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.
View all properties

Choose what matters most at hotels with a pool in Upperville

Breakfast included
4 stars

Top Upperville Hotel Reviews

Lansdowne Resort and Spa

Lansdowne Resort and Spa

8/10 Good
"Food at wedding venue was excellent. Only reason review was not excellent was that the previous occupant of our room evidently had set the alarm clock for 5:30 am on a holiday when we planned to sleep in and it was difficult to turn it off. No apology was offered for not making sure it had been turned off."
Caleb 1-night trip
Posted less than an hour ago
Lansdowne Resort and Spa

Frequently asked questions

What are some accommodations with pools in Upperville?
Spark by Hilton Winchester: Offers a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. Lansdowne Resort and Spa: Provides a children's pool, a seasonal outdoor pool, and 2 restaurants. Salamander Resort And Spa: Features a health club, an indoor pool, and daily. TRU By Hilton Winchester: Offers 2 restaurants, an indoor pool, and a full-service spa. The George Washington Hotel, A Wyndham Grand Hotel: Features daily, an indoor pool, and free self parking.
What is there to see and do in Upperville?
Surround yourself with nature at Upperville Park. Discover sights such as Sky Meadows State Park during your stay.
When is the best time to book a hotel with a pool in Upperville?
You may want to think about a place to stay with an outdoor swimming pool if you will be visiting Upperville in the hottest months of July, August, or June when the average temperature is 72°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temperature is 37°F.