Photo by Michael Gibson

Search Hotels with Pool in Upperville

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Tonight
28 Dec - 29 Dec
Tomorrow
29 Dec - 30 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Upperville hotels with a pool

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool loungers
Goodstone Inn & Restaurant

Goodstone Inn & Restaurant

Goodstone Inn & Restaurant
4.0 star property
Middleburg
9.6 out of 10, Exceptional, (48)
"It was a delightful quaint exclusive country inn - a real treat to stay. "
United States
Amanda
The price is Rp6.346.355
Rp8.723.810 total
includes taxes & fees
29 Dec - 30 Dec
Goodstone Inn & Restaurant
Couples treatment room(s), sauna, hot tub, steam room
Salamander Resort And Spa

Salamander Resort And Spa

Salamander Resort And Spa
5.0 star property
Middleburg
9.2 out of 10, Wonderful, (376)
"Staff was very helpful and pleasant. "
United States
Cheryl A.
The price is Rp8.523.205
Rp10.586.188 total
includes taxes & fees
7 Jan - 8 Jan 2026
Salamander Resort And Spa
Seasonal outdoor pool
Twi-Lite Inn

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
Front Royal
8.2 out of 10, Very good, (541)
"Clean, comfortable room. Staff was nice and I really enjoyed my stay. Motel was in a high traffic area, but still a quiet stay"
United States
Daniel
The price is Rp1.038.190
Rp1.155.572 total
includes taxes & fees
29 Dec - 30 Dec
Twi-Lite Inn
Free daily full breakfast
Inn at Evergreen

Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.4 out of 10, Exceptional, (133)
"Very nice cozy place and the breakfast was included and very delicious. Only issue I had was the footsteps of upstairs guests came through."
United States
Chiharu
Inn at Evergreen
Indoor pool
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1001)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is Rp1.633.977
Rp1.802.277 total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Seasonal outdoor pool, open 9 AM to 10 PM, pool loungers
Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
Stephens City
8.2 out of 10, Very good, (807)
"Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. "
United States
Rose
The price is Rp1.239.130
Rp1.348.174 total
includes taxes & fees
30 Dec - 31 Dec
Holiday Inn Express Winchester South-Stephens City by IHG
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.6 out of 10, Exceptional, (175)
"This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. "
United States
DONNA
The price is Rp3.834.605
Rp4.229.569 total
includes taxes & fees
4 Jan - 5 Jan 2026
L'Auberge Provencale Inn & Restaurant
Indoor pool, seasonal outdoor pool
Lansdowne Resort and Spa

Lansdowne Resort and Spa

Lansdowne Resort and Spa
4.0 star property
Leesburg
8.8 out of 10, Excellent, (1001)
"Great place"
United States
Joyce
The price is Rp3.006.565
Rp4.048.941 total
includes taxes & fees
30 Dec - 31 Dec
Lansdowne Resort and Spa
Seasonal outdoor pool
Glen Gordon Manor

Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (95)
"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
United States
KYLE
The price is Rp4.839.305
Rp5.289.411 total
includes taxes & fees
20 Jan - 21 Jan 2026
Glen Gordon Manor
Indoor pool
Hampton Inn by Hilton Gainesville-Haymarket

Hampton Inn by Hilton Gainesville-Haymarket

Hampton Inn by Hilton Gainesville-Haymarket
2.5 star property
Gainesville
8.8 out of 10, Excellent, (994)
"Friendly staff, clean room, good breakfast "
United States
Vivian
The price is Rp1.663.281
Rp1.896.141 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn by Hilton Gainesville-Haymarket
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

Top Upperville Hotel Reviews

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Great staff, clean room"
John 1-night trip
Posted 10 days ago
Quality Inn Winchester
Salamander Resort And Spa

Salamander Resort And Spa

10/10 Excellent
"."
Ivanti 2-night trip
Posted 3 weeks ago
Salamander Resort And Spa

Frequently asked questions

What are some accommodation options with pools in Upperville?
Hilton Garden Inn Dulles North: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Lansdowne Resort and Spa: Offers a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Salamander Resort And Spa: Provides a children's pool, a seasonal outdoor pool and 2 restaurants. Microtel Inn & Suites by Wyndham Winchester: Features daily, an indoor pool and free self parking. La Quinta Inn & Suites by Wyndham Winchester: Offers buffet, an indoor pool and complimentary high-speed (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 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.