The Best Hotels with a Pool in Upperville, VA from AED 385 in 2026

Q: What are some accommodations with pools in Upperville?

Lansdowne Resort and Spa : Resort located near One Loudoun. Features a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. Spark by Hilton Winchester : Provides a health club, an indoor pool, and daily. TRU By Hilton Winchester : Features a children's pool, a seasonal outdoor pool, and 2 restaurants. Salamander Resort And Spa : Offers 2 restaurants, an indoor pool, and a full-service spa. Silo Tiny House Cabin : Provides a snack bar/deli, an indoor pool, and complimentary wired internet access.

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Our top choices for Upperville hotels with a pool

TRU By Hilton Winchester

Winchester

Splash into fun at this pet-friendly hotel with a pristine indoor pool and health club.

AED 344 total

includes taxes & fees

5 Jul - 6 Jul

Hampton Inn Winchester N/Conference Center, VA

Winchester

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

AED 474 total

includes taxes & fees

4 Jul - 5 Jul

Clarion Inn Harpers Ferry - Charles Town

Harpers Ferry

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

AED 421 total

includes taxes & fees

28 Jul - 29 Jul

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.

AED 543 total

includes taxes & fees

14 Jul - 15 Jul

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.

AED 436 total

includes taxes & fees

5 Jul - 6 Jul

La Quinta Inn & Suites by Wyndham Winchester

Winchester

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

AED 435 total

includes taxes & fees

1 Jul - 2 Jul

Baymont by Wyndham Warrenton

Warrenton

Splash into summer at this Warrenton motel featuring a seasonal outdoor pool and 24-hour fitness center.

AED 274 total

includes taxes & fees

9 Jul - 10 Jul

Quality Inn Winchester

Winchester

Dive into crystal-clear waters at this well-maintained hotel featuring a seasonal outdoor pool surrounded by pleasant landscaping.

AED 414 total

includes taxes & fees

19 Jul - 20 Jul

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Choose what matters most at hotels with a pool in Upperville

Breakfast included

4 stars

Top Upperville Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Clean room. Excellent overall"

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"This was the neatest place I've stayed at. The building is gorgeous and they've kept the historic aspects of it very nice. Beds were very comfortable. Shower was hot and had good pressure. Staff was all very friendly. There's a nice pub with live music right next door. Lots to do and see in this town. I was very pleased we picked this spot as a halfway point to our destination"

Best Western Leesburg Hotel & Conference Center

8/10 Good

"Clean, decent hotel. Wanted to charge us for an early check-in, which seemed excessive considering that they weren’t full, but in the end we got in an hour early and it was a good stay. Pool area needs improvement, my son’s feet got caught on exposed metal bolts and cut up his feet. Clean rooms."

Spark by Hilton Winchester

8/10 Good

"Overall great experience - with that said their computer system wasnt working right. I was charged for the room twice (over and above the already charged payment from Expedia) and also a $100 security deposit. I brought it up the next day and it was immediately corrected. Nice hotel, good local, and friendly staff."

Baymont by Wyndham Warrenton

10/10 Excellent

"Easy to book online. When i arrived at the site the desk clerk didnt want to check me in. He said that i shouldn't have been able to book a room because he was booked up. I told him that online it said 6 rooms left. He said well someone is not going to have a room because he already had other arrivals. I explain to him what the website said and I had my reservation number, I was an arrival and I needed to be checked in after driving for 12 hours. He finally processed my reservation and I was able to stay. He said it was a miscommunication between your website and his screen. Idk"

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Frequently asked questions

What are some accommodations with pools in Upperville?

Lansdowne Resort and Spa: Resort located near One Loudoun. Features a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. Spark by Hilton Winchester: Provides a health club, an indoor pool, and daily. TRU By Hilton Winchester: Features a children's pool, a seasonal outdoor pool, and 2 restaurants. Salamander Resort And Spa: Offers 2 restaurants, an indoor pool, and a full-service spa. Silo Tiny House Cabin: Provides a snack bar/deli, 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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