Search Hotels with Pool in Upperville

  • 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 Pool

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

Our top choices for Upperville hotels with a pool

Indoor pool

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town
2.5 star property
Harpers Ferry
7.8 out of 10, Good, (1,004 reviews)
  • cleanliness
    Scenic indoor pool provides year-round escape for travellers seeking relaxation after park adventures.
The price is ฿3,144
฿3,522 total
includes taxes & fees
17 Jun - 18 Jun
Clarion Inn Harpers Ferry - Charles Town
Indoor pool

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1,001 reviews)
  • cleanliness
    Float in style at this historic Winchester hotel featuring an elegant indoor pool and indulgent spa services.
The price is ฿3,987
฿4,518 total
includes taxes & fees
11 Jun - 12 Jun
The George Washington Hotel, A Wyndham Grand Hotel
Seasonal outdoor pool

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
Winchester
9.2 out of 10, Wonderful, (894 reviews)
  • cleanliness
    Splash into summer with panoramic mountain views from this seasonal outdoor pool experience.
The price is ฿3,506
฿3,972 total
includes taxes & fees
8 Jun - 9 Jun
Hampton Inn Winchester N/Conference Center, VA
Indoor pool

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Dive into relaxation at this mountain hotel's pristine pool, just steps from a 24-hour fitness centre for active travellers.
The price is ฿4,121
฿4,587 total
includes taxes & fees
28 Jun - 29 Jun
Hampton Inn Front Royal
Indoor pool

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,466 reviews)
  • cleanliness
    Make a splash at this Winchester hotel with an indoor pool and fitness centre for all seasons.
The price is ฿3,162
฿3,441 total
includes taxes & fees
2 Jun - 3 Jun
Microtel Inn & Suites by Wyndham Winchester
Indoor pool

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (892 reviews)
  • cleanliness
    Splash into fun at this pet-friendly hotel with a pristine indoor pool and health club.
The price is ฿3,856
฿4,195 total
includes taxes & fees
14 Jun - 15 Jun
TRU By Hilton Winchester
Indoor pool

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (985 reviews)
  • cleanliness
    Experience refreshing swims any season at this indoor pool hotel with comfy beds and on-site dining.
The price is ฿3,492
฿3,799 total
includes taxes & fees
11 Jun - 12 Jun
Courtyard by Marriott Winchester
Outdoor pool

Holiday Inn Express Charles Town by IHG

Holiday Inn Express Charles Town by IHG
2.5 star property
Charles Town
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Dive into summer fun with this hotel's refreshing outdoor pool and complimentary casino shuttle service.
The price is ฿3,427
฿3,872 total
includes taxes & fees
7 Jun - 8 Jun
Holiday Inn Express Charles Town by IHG
Indoor pool

Hampton Inn & Suites Charles Town

Hampton Inn & Suites Charles Town
2.5 star property
Charles Town
9.4 out of 10, Exceptional, (1,000 reviews)
  • cleanliness
    Take a dip in the pristine indoor pool at this Charles Town retreat, where aquatic relaxation meets comfortable luxury.
The price is ฿4,255
฿4,766 total
includes taxes & fees
3 Jun - 4 Jun
Hampton Inn & Suites Charles Town
Indoor pool

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (867 reviews)
  • cleanliness
    Splash into Winchester luxury with an indoor pool retreat in a historical Art Deco hotel.
The price is ฿3,024
฿3,290 total
includes taxes & fees
15 Jun - 16 Jun
Fairfield Inn & Suites by Marriott Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at hotels with a pool in Upperville

Breakfast included
4 stars

Top Upperville Hotel Reviews

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

10/10 Excellent
"With a clean room with two incredibly comfortable beds with super soft pillows, 15 minutes from Shenandoah entrance, close to shopping and stores and plenty of restaurants, the Double Tree was the best spot for a nature weekend. My wife and I loved every bit of it. We loved the free cookies at check in, the beautiful views of rolling hills and the golf course, the location of the hotel and everything they offered. It was a perfect getaway. The beds were clean, the room surprisingly had a good smart TV even though we still used our fire stick, the bathroom was spotless!"
Christian 1-night trip
Posted 11 hours ago
DoubleTree by Hilton Front Royal Blue Ridge Shadows

Frequently asked questions

What are some accommodation options 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 that has an outdoor pool if you're planning to visit Upperville in the hottest months of July, August or June, when the average temperature is 22°C. Accommodation offering an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temperature is 3°C.