A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.

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

Tonight
28 Sep - 29 Sep
Tomorrow
29 Sep - 30 Sep
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Upperville hotels with a pool

1. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
Winchester
  • Splash into Winchester luxury with an indoor pool retreat in a historical Art Deco hotel.
AED 340
AED 379 total
includes taxes & fees
5 Oct - 6 Oct
Fairfield Inn & Suites by Marriott Winchester

2. Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
Winchester
  • Splash into summer with panoramic mountain views from this seasonal outdoor pool experience.
AED 352
AED 399 total
includes taxes & fees
19 Oct - 20 Oct
Hampton Inn Winchester N/Conference Center, VA

3. Hampton Inn Front Royal

Hampton Inn Front Royal
Front Royal
  • Dive into relaxation at this mountain hotel's pristine pool, just steps from a 24-hour fitness center for active travelers.
AED 449
AED 499 total
includes taxes & fees
11 Oct - 12 Oct
Hampton Inn Front Royal

4. Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
Winchester
  • Make a splash at this Winchester hotel with an indoor pool and fitness center for all seasons.
AED 373
AED 415 total
includes taxes & fees
25 Oct - 26 Oct
Microtel Inn & Suites by Wyndham Winchester

5. TRU By Hilton Winchester

TRU By Hilton Winchester
Winchester
  • Splash into fun at this pet-friendly hotel with a pristine indoor pool and health club.
AED 358
AED 399 total
includes taxes & fees
4 Oct - 5 Oct
TRU By Hilton Winchester

6. Hampton Inn by Hilton Gainesville-Haymarket

Hampton Inn by Hilton Gainesville-Haymarket
Gainesville
  • Year-round aquatic bliss at this hotel with an indoor pool and fitness options.
AED 387
AED 441 total
includes taxes & fees
18 Oct - 19 Oct
Hampton Inn by Hilton Gainesville-Haymarket

7. L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
Boyce
  • Soak in seasonal sunshine at this serene pool retreat with loungers and garden views.
AED 955
AED 1,054 total
includes taxes & fees
29 Sep - 30 Sep
L'Auberge Provencale Inn & Restaurant

8. SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
Winchester
  • Refresh in the indoor pool at this hotel that offers a firepit and streamlined amenities near top Winchester attractions.
AED 449
AED 500 total
includes taxes & fees
4 Oct - 5 Oct
SpringHill Suites by Marriott Winchester

9. Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
  • Splash into year-round aquatic bliss at this inviting hotel with an indoor pool paradise.
AED 404
AED 461 total
includes taxes & fees
4 Oct - 5 Oct
Holiday Inn Winchester Se-Historic Gateway by IHG

10. Holiday Inn Express Hotel & Suites Warrenton by IHG

Holiday Inn Express Hotel & Suites Warrenton by IHG
Warrenton
  • Soak up the sun at this delightful hotel with a seasonal outdoor pool and fitness center.
AED 511
AED 558 total
includes taxes & fees
4 Oct - 5 Oct
Holiday Inn Express Hotel & Suites Warrenton by IHG
View all properties

Choose what matters most at hotels with a pool in Upperville

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Upperville Hotel Reviews

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

8/10 Good
"It could be a very nice hotel, but it needs some maintenance."
Nancy 2-night trip
Posted 3 hours ago
Clarion Inn Harpers Ferry - Charles Town
Hampton Inn Front Royal

Hampton Inn Front Royal

10/10 Excellent
"Really enjoyed our stay at the Hampton Inn, in Front Royal. My wife and I took a trip to do a hiking weekend in Shenandoah National Park. With the hotel being close to the park, as well as just outside a relatively large town, so we'd have stuff to do in the evenings, the location was great. The room was very comfortable, and staff were extremely friendly and helpful. Everything was clean, and they had a great breakfast (which opened early...key for getting a really early start to the day before we hit the trails) The only downside was, we did pick the hotel based off all those factors, but as well as it having an indoor pool. After a day hiking up and down Old Rag, a late afternoon in the pool to decompress and recover was going to be what we needed...unfortunately we did not find out until after we arrived, the pool was out of service. So that was a little disappointing, but we made the best of it."
Garrett 2-night trip
Posted 7 hours ago
Hampton Inn Front Royal
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

8/10 Good
"The parking lot has no control. Everyone parked how ever they want to park. The some of the trailers parked and blocked 6 parking space"
Suat Serol and Ruya Mahdum 1-night trip
Posted 12 hours ago
La Quinta Inn & Suites by Wyndham Winchester
Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"I brought my wife up here for her birthday weekend. The room we were staying in had a beautiful view of the environment and the mountains. The wait staff was very nice as we did in-room dining for our breakfast and we ate at the Cotton Rye restaurant for dinner. And the food was pretty good. My wife used the massage service and it was very lovely. We both did the Floating Bath service, and that was a pleasant experience. Things can get a little pricey around here. But overall, it was a very good stay. And we would love to come back."
Jamiil 3-night trip
Posted 19 hours ago
Lansdowne Resort and Spa
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"a"
James 2-night trip
Posted 23 hours ago
The George Washington Hotel, A Wyndham Grand Hotel
Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"Very nice and welcoming staff, nice location, pool and included breakfast available!"
carrie 1-night trip
Posted 1 day ago
Spark by Hilton Winchester
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"Good bed, nice size room, desk clerk was very helpful in getting us on the non-highway side of the property (which was then very quiet). Breakfast OK, lots of restaurants around the property and a movie theatre. Good location for Winchester"
Christopher 1-night trip
Posted 3 days ago
Country Inn & Suites by Radisson, Winchester, VA

Frequently asked questions

What are some accommodations with pools in Upperville?
Salamander Resort And Spa: Features a children's pool, a seasonal outdoor pool, and 2 restaurants. The George Washington Hotel, A Wyndham Grand Hotel: Offers 2 restaurants, an indoor pool, and a full-service spa. Lansdowne Resort and Spa: Provides a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. Travelodge by Wyndham Winchester: Offers a health club, an indoor pool, and daily. TRU By Hilton Winchester: Features buffet, an indoor pool, and complimentary wired internet access.
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.