TOP Hotels with Swimming Pool in Upperville, VA for 2026

Q: What are some accommodation options with pools in Upperville?

Spark by Hilton Winchester : Offers a health club, an indoor pool and daily. TRU By Hilton Winchester : Resort located near One Loudoun. Provides a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Lansdowne Resort and Spa : 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. Travelodge by Wyndham Winchester : Provides daily, an indoor pool and free self parking.

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Our top choices for Upperville hotels with a pool

Clarion Inn Harpers Ferry - Charles Town

Harpers Ferry

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

₹10,390 total

includes taxes & fees

1 Jul - 2 Jul

Hampton Inn Winchester N/Conference Center, VA

Winchester

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

₹12,212 total

includes taxes & fees

24 Jun - 25 Jun

TRU By Hilton Winchester

Winchester

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

₹8,059 total

includes taxes & fees

5 Jul - 6 Jul

Seasonal outdoor pool, open 10:00 AM to 10:00 PM, pool umbrellas

Baymont by Wyndham Front Royal Near Shenandoah National Park

Front Royal

Summer bliss awaits at this refreshed hotel with seasonal pool near Shenandoah National Park.

₹6,531 total

includes taxes & fees

29 Jun - 30 Jun

Fairfield Inn & Suites by Marriott Winchester

Winchester

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

₹9,532 total

includes taxes & fees

23 Jun - 24 Jun

Quality Inn Winchester

Winchester

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

₹10,298 total

includes taxes & fees

1 Jul - 2 Jul

Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

Splash into year-round aquatic bliss at this inviting hotel with an indoor pool paradise.

₹9,852 total

includes taxes & fees

28 Jun - 29 Jun

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.

₹13,969 total

includes taxes & fees

1 Jul - 2 Jul

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Choose what matters most at hotels with a pool in Upperville

Breakfast included

4 stars

Top Upperville Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"What a beautiful hotel. This hotel has so much history and charm. The rooms are clean and beautiful. The parking garage is right beside it making it so convenient. The location of the hotel was amazing only one block from restaurant and shops."

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"