The Best Hotels with a Pool in Upperville, VA from AED 379 in 2026

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

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Our top choices for Upperville hotels with a pool

A swimming pool with a tiled deck, lounge chairs, and a sunshade.

A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.

A coffee station with multiple coffee dispensers and a sign above.

1. 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

A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.

A lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.

A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.

A hotel lobby with a reception desk, refrigerated display cases, shelves with snacks, and a trash bin.

2. 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

A swimming pool with clear water, surrounded by large windows offering views of greenery.

A modern dining area with tables and chairs, large windows, and a flat-screen TV on the wall.

A hotel room with a gray sofa, a bed with a blue headboard, a painting of a landscape, and a lamp on the nightstand.

3. 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

An indoor swimming pool with lounge chairs and a lifeguard chair.

A modern lounge area with seating, a TV, and a children's play area.

A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.

A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.

4. 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

An indoor swimming pool with clear lane markings, a lifeguard chair, and a safety ring on the wall.

A modern lounge area with seating arrangements, including sofas and chairs, and a large window providing a view outside.

A self-service beverage station with a refrigerated drink dispenser, a coffee machine, and a variety of snacks.

A modern hotel building with a prominent 'TRU by Hilton' sign, multiple floors, and a parking lot in front.

5. 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

An indoor swimming pool with clear blue water, surrounded by tiled flooring and equipped with a pool ladder.

A spacious living area with a sofa, armchairs, a coffee table, and a dining area with chairs and a table.

A gym with treadmills, exercise balls, and a pool in the background.

A modern kitchen with wooden cabinets, a coffee machine, and a toaster.

6. 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

A two-story house with a swimming pool, outdoor furniture, and a covered patio area.

A dining area with tables set for service, large windows with views of greenery, and a chandelier.

A covered porch with wooden benches and potted plants, a tiled floor, and a view of a grassy yard.

A covered porch with white columns, a bench, and hanging flower baskets.

7. 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

An indoor swimming pool with clear water, metal railings, and lounge chairs.

An outdoor patio with a fire feature, seating, and a covered area.

A modern hotel with a covered entrance, a sign reading "SPRINGHILL SUITES BY MARRIOTT," and a landscaped area with plants.

A modern hotel lobby with a large dining area, wooden accents, and contemporary lighting fixtures.

8. 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

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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

8/10 Good

"It could be a very nice hotel, but it needs some maintenance."

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."

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"

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."

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"a"

Spark by Hilton Winchester

10/10 Excellent

"Very nice and welcoming staff, nice location, pool and included breakfast available!"

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"

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.

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Check availability on Upperville Hotels with a Pool

Our top choices for Upperville hotels with a pool

1. Fairfield Inn & Suites by Marriott Winchester