The Best Upperville Hotels with Pools from $69 - Hotels with indoor pools in Upperville, VA

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

Room, 2 Queen Beds, Non Smoking | Egyptian cotton sheets, premium bedding, desk, blackout drapes

1. La Quinta Inn & Suites by Wyndham Winchester

Winchester

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

$107 nightly

$119 total

Aug 27 - Aug 28

Total with taxes and fees

Select Comfort beds, desk, laptop workspace, blackout drapes

2. Fairfield Inn & Suites by Marriott Winchester

Winchester

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

$93 nightly

$103 total

Aug 20 - Aug 21

Total with taxes and fees

3. DoubleTree by Hilton Front Royal Blue Ridge Shadows

Front Royal

Splash into a refreshing mountain retreat where the indoor pool meets scenic golf views.

$122 nightly

$135 total

Aug 24 - Aug 25

Total with taxes and fees

4. 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.

$122 nightly

$136 total

Aug 23 - Aug 24

Total with taxes and fees

5. TRU By Hilton Winchester

Winchester

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

$98 nightly

$109 total

Aug 23 - Aug 24

Total with taxes and fees

Room, 2 Queen Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

6. Country Inn & Suites by Radisson, Winchester, VA

Winchester

Splash into a year-round swimming oasis with a refreshing indoor pool sanctuary at this Winchester hotel.

$95 nightly

$105 total

Sep 8 - Sep 9

Total with taxes and fees

Seasonal outdoor pool, open 7:00 AM to 10:00 PM, sun loungers

7. TownePlace Suites by Marriott Front Royal

Front Royal

Dive into seasonal splash sessions with 24-hour fitness access at this Front Royal escape.

$141 nightly

$155 total

Sep 1 - Sep 2

Total with taxes and fees

Suite, 1 King Bed (Additional Living Area) | In-room safe, desk, laptop workspace, blackout drapes

8. Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

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

$96 nightly

$107 total

Aug 23 - Aug 24

Total with taxes and fees

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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

"check in was easy, nice staff and the restaurant was good breakfast was a little sparse."

Travelodge by Wyndham Winchester

8/10 Good

"Old facility but clean and nice"

Spark by Hilton Winchester

10/10 Excellent

"Such a cute and clean hotel! A great place to stay if you need to go to Shenandoah University. Restaurants were within walking distance. The hotel also has a nice continental breakfast but if you’re wanting more there’s a Waffle House right outside the front door."

Quality Inn Winchester

10/10 Excellent

"Room was clean and well maintained"

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Amazing stay. The front desk woman was so kind when we walked in!! It was much appreciated after a long day of traveling. Clean room, excellent coffee in the morning and just a really nice stay."

Hampton Inn Front Royal

10/10 Excellent

"This is the 2nd year we have stayed at your hotel. Your location, cleanliness, & service is great for our needs."

Salamander Resort And Spa

8/10 Good

"The property and staff are amazing. Lots to do if you bring the kiddos, the kids camp let's adults relax and enjoy amenities. The one thing the property can work on is the food menu; more variety is needed. The Red Horse Tavern is a 5-minute walk into town and has the best food!! "

Frequently asked questions

What are some accommodations with pools in Upperville?

Lansdowne Resort and Spa: Features a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. Salamander Resort And Spa: Offers a children's pool, a seasonal outdoor pool, and 2 restaurants. Holiday Inn Winchester Se-Historic Gateway by IHG: Provides a snack bar/deli, an indoor pool, and complimentary wired internet access. Silo Tiny House Cabin: Features complimentary wired internet access, an indoor pool, and free self parking. Spark by Hilton Winchester: Offers 2 restaurants, an indoor pool, and a full-service spa.

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. La Quinta Inn & Suites by Wyndham Winchester

2. Fairfield Inn & Suites by Marriott Winchester