The Best Hotels with a Pool in Upperville, VA from NT$3,161 in 2026

Q: 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.

Welcome sign to Upperville Virginia in Fauquier County.

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Our top choices for Upperville hotels with a pool

Hampton Inn Winchester N/Conference Center, VA

Winchester

Splash into summer with panoramic mountain views from this seasonal outdoor pool experience.

NT$3,817 total

includes taxes & fees

Jun 9 - Jun 10

Holiday Inn Express Charles Town by IHG

Charles Town

Dive into summer fun with this hotel's refreshing outdoor pool and complimentary casino shuttle service.

NT$3,722 total

includes taxes & fees

Jun 29 - Jun 30

The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

Float in style at this historic Winchester hotel featuring an elegant indoor pool and indulgent spa services.

NT$5,294 total

includes taxes & fees

Jun 18 - Jun 19

La Quinta Inn & Suites by Wyndham Winchester

Winchester

Dive into the inviting indoor pool, perfect for year-round swims at this clean, modern hotel.

NT$4,403 total

includes taxes & fees

Jun 3 - Jun 4

Clarion Inn Harpers Ferry - Charles Town

Harpers Ferry

Scenic indoor pool provides year-round escape for travelers seeking relaxation after park adventures.

NT$3,255 total

includes taxes & fees

Jun 30 - Jul 1

Fairfield Inn & Suites by Marriott Winchester

Winchester

Splash into Winchester luxury with an indoor pool retreat in a historical Art Deco hotel.

NT$3,162 total

includes taxes & fees

Jun 14 - Jun 15

TownePlace Suites by Marriott Front Royal

Front Royal

Dive into seasonal splash sessions with 24-hour fitness access at this Front Royal escape.

NT$4,457 total

includes taxes & fees

Jun 7 - Jun 8

Country Inn & Suites by Radisson, Winchester, VA

Winchester

Splash into a year-round swimming oasis with a refreshing indoor pool sanctuary at this Winchester hotel.

NT$3,195 total

includes taxes & fees

Jun 22 - Jun 23

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Choose what matters most at hotels with a pool in Upperville

Breakfast included

4 stars

Top Upperville Hotel Reviews

Spark by Hilton Winchester

8/10 Good

"Staff was very nice"

The George Washington Hotel, A Wyndham Grand Hotel

8/10 Good

"It may have been the number one hotel in town 30 years ago. Today, however, the balance between price and quality has shifted heavily toward the price, while the quality has unfortunately fallen behind. We stayed in a suite directly under the roof, and throughout our entire stay there was a loud banging noise every 35–45 minutes. The hotel was unable to eliminate the problem, which meant we were woken up repeatedly during the night. Not exactly ideal when attending a large family event and trying to get proper rest. It might be a good idea for the hotel to hire a professional to properly repair the issue instead of relying solely on the hotel handyman. I m not a typically complainer, but if you pay the monthly cost of a midclass car leasingrate per hotel night, you might expect, at least to have and undisturbed sleep."

Carradoc Hall Hotel & Conference Center by The Red Collection

4/10 Poor

"This property was supposedly renovated recently. The contractors they had do the job were terrible! There was paint all over the ceiling and the bathtub in the bathroom had old, dried caulking all around the bathtub. When we arrived, we had to ask for toilet paper, soap, a remote control for the TV, and also realized the refrigerator was broken. Also, the restaurant there was closed on the weekends and we were not told that we would have no breakfast on Monday because it was memorial day and they closed the restaurant for that day as well. Pretty sad."

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.

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Our top choices for Upperville hotels with a pool