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Hotel Name
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Upperville Hotels with Outdoor or Indoor Pools

Hampton Inn by Hilton : 9800 Winchester Rd. 9800 Winchester Rd., Front Royal, VA 22630 ~16.61 miles west of Upperville
  • Includes a pool: We have an indoor pool which is open from 8am-10pm
  • Three Star Suburban hotel
  • Accessible parking
  • Close to historic sites
Quality Inn Skyline Drive in Front Royal 10 South Commerce Ave., Front Royal, VA 22630 ~16.71 miles west of Upperville
  • Pool details: Outdoor poolOpen 10:00 a.m. to 10:00 p.m. End of May to First of September
  • Good pool
  • Great pool
  • Two star Downtown hotel
From$65
Average 3.0 /5Reviews Call
Aloft Winchester 1055 Millwood Pike, Winchester, VA 22602 ~18.29 miles northwest of Upperville
  • Includes a pool: Splash, our Indoor Pool is open 6am-11pm
  • Pool in need of cleaning
  • Dirty pool, said 67%
  • Mid-scale Suburban property
From$85
Very Good 4.0 /5Review Score Call
Sleep Inn & Suites : 140 Costello Dr. 140 Costello Dr., Winchester, VA 22602 ~18.37 miles northwest of Upperville
  • Pool details: We have indoor heated pool, open all year round. Open 09:00am to 10:00pm. There is a pool lift available with a battery and a remote control.Size: 15 x 28 feet.
  • 2-star Suburban property
From$60
Very Good 4.0 /5Read Reviews Call
Holiday Inn Winchester Se Historic Gateway 333 Front Royal Pike, Winchester, VA 22602 ~18.46 miles northwest of Upperville
  • Has swimming pool
  • Midscale Suburban hotel
From$83
Very Good 4.5 /5Read Reviews Call
Fairfield & Suites by Marriott Winchester
+1-800-881-1523
250 Front Royal Pike, Winchester, VA 22601 ~18.46 miles northwest of Upperville
  • Pool available: Indoor pool open daily from 9:00AM - 10:00PM
  • Horrible pool
  • Pool should be renewed
  • Indoor pool doesn't open
  • Only complaint was the pool
  • 3 star Suburban property
From$93
Very Good 4.0 /5Read Reviews Call
Comfort Inn Stephens City : 167 Town Run Lane 167 Town Run Lane, Stephens City, VA 22655 ~18.49 miles west of Upperville
  • Includes a pool: The outdoor seasonal pool is open from 9:00am to 9:00pm
  • 3-star Highway property
From$60
Average 3.5 /5Reviews Call
Holiday Inn Express Winchester South / Stephens Ci in Stephens City 165 Town Run Lane, Stephens City, VA 22655 ~18.50 miles west of Upperville
  • Pool in hotel
  • 3 star Rural hotel
Travelodge Winchester - Winchester 160 Front Royal Pike, Winchester, VA 22602 ~18.54 miles northwest of Upperville
  • Has swimming pool: Pool is outdoor. It generally opens by middle of May and closes by end of September. Again it depends on weather conditions at that time.
  • Clean pool area
  • Two-star Suburban property
Country Inn & Suites by Carlson Winchester Va 141 Kernstown Commons Blvd., Winchester, VA 22602 ~18.58 miles west of Upperville
  • Pool details: Indoor heated pool & hot tub open daily from 6am-12am (midnight)
  • Pool is good
  • Great pool
  • Nice pool
  • Heated pool
  • Affordable Mountain property
From$65
Very Good 4.5 /5Reviews Call
Towneplace Suites by Marriott Winchester in Winchester 170 Getty Ln, Winchester, VA 22603 ~18.77 miles northwest of Upperville
  • We have a pool
  • 3-star Suburban hotel
Best Western Lee Jackson Inn & Conference Center in Winchester 711 Millwood Ave., Winchester, VA 22601 ~18.78 miles northwest of Upperville
  • Pool details: Labor day to Memorial DayOutdoor
  • Economical Highway hotel
From$49
Very Good 4.0 /5Reviews Call
Hampton Inn Winchester University / Mall Area : 640 East Jubal Early Dr. 640 East Jubal Early Dr., Winchester, VA 22601 ~18.96 miles northwest of Upperville
  • Pool details: Seasonal Outdoor Pool that is open from 8 am to 10 pm
  • Excellent pool
  • Great pool
  • Dip in the pool which was very clean
  • Lovely outdoor pool
  • Nice pool
  • 3-star Highway hotel
Hampton Inn & Conference Center 1204 Berryville Ave., Winchester, VA 22601 ~18.98 miles northwest of Upperville
  • Pool available: We feature a beautiful outdoor pool and sundeck, which is open Memorial Day through Labor Day. The pool is open in season from 9 am - 10 pm.
  • Mid-scale Highway hotel
From$60
Very Good 4.5 /5Review Score Call
Baymont Inn & Suites 7379 Comfort Inn Dr., Warrenton, VA 20187 ~19.06 miles south of Upperville
  • Pool in hotel: We have a seasonal 15x25ft in ground pool. Plenty of sitting area, umbrellas and lounge chairs. Pool is equipped with a ADA lift for easy access to the pool. open 10am-10pm usually May through September. Complimentary Pool Towels provided.
  • 3 star Suburban hotel
Wingate by Wyndham
+1-800-997-5149
150 Wingate Dr., Winchester, VA 22601 ~19.15 miles northwest of Upperville
  • Includes a pool
  • Excellent pool
  • Great pool
  • Nice pool
  • 3 star Downtown hotel
Hilton Garden Inn 120 Wingate Dr., Winchester, VA 22601 ~19.21 miles northwest of Upperville
  • Pool details: Indoor Pool and Whirlpool. Open 5AM - 10PM.
  • Affordable Highway property
Holiday Inn Express Hotel & Suites in Warrenton 410 Holiday Court, Warrenton, VA 20186 ~19.44 miles south of Upperville
  • Pool details: We have an outdoor, seasonal pool that is open between Labor Day and Memorial Day, between the hours of 8:00am and 10:00pm.
  • Mid-scale Suburban property
Comfort Suites Leesburg 80 Prosperity Ave., Leesburg, VA 20175 ~19.93 miles east of Upperville
  • Pool in hotel: Indoor Heated Pool with whirlpool. Outdoor patio connects to indoor pool, sun chairs available on the patio.
  • 3 star property
From$100
Very Good 4.5 /5Read Reviews Call
Best Western Leesburg Hotel & Conference Center - Leesburg 726 East Market St., Leesburg, VA 20176 ~20.02 miles east of Upperville
  • Pool details: Our lovely seasonal outdoor swimming pool sits in a private courtyard. The pool is open Memorial Day to Labor Day as a minimum; we open prior to Memorial Day and keep the pool beyond Labor Day, weather permitting.
  • Excellent pool
  • Great pool
  • Pool was a joy
  • Lovely pool
  • Midscale Suburban hotel
From$70
Very Good 4.0 /5Reviews Call
Homewood Suites by Hilton Leesburg Va in Leesburg 115 Fort Evans Rd. Ne, Leesburg, VA 20176 ~20.25 miles east of Upperville
  • Pool details: Outdoor PoolOpen from 8:00 AM to 10:00 PMPool open every year from Memorial Day to Labor Day
  • Midscale Downtown hotel
Hampton Inn & Suites Leesburg Va : 117 Fort Evans Rd. Ne 117 Fort Evans Rd. Ne, Leesburg, VA 20176 ~20.26 miles east of Upperville
  • Pool available: Indoor Heated Pool524 square feet 3-5ft DeepOpen 6am-10pm
  • Cheap Suburban property
From$97
Very Good 4.0 /5Read Reviews Call
Comfort Inn : 1601 Martinsburg Pike
+1-888-283-3404
1601 Martinsburg Pike, Winchester, VA 22603 ~20.59 miles northwest of Upperville
  • Includes a pool
  • Excellent pool
  • Great pool
  • Inexpensive Highway hotel
From$65
Very Good 4.0 /5Read Reviews Call
Clarion Inn Leesburg : 1500 East Market St. 1500 East Market St., Leesburg, VA 20176 ~20.86 miles east of Upperville
  • Pool in hotel: Large outdoor pool. Private and intimate seating areas on porches and verandas.9am-10pm Memorial Day to Labor Day
  • Outdoor pool was big and very clean
  • Horrible pool
  • Pool should be renewed
  • No indoor pool
  • Swimming pool closed
  • Pool was not open even
  • Three Star Highway property
Holiday Inn Express & Suites
+1-888-690-5281
142 Fox Ridge Lane, Winchester, VA 22603 ~21.51 miles northwest of Upperville
  • Pool available: 9am-10pmIndoor with Jacuzzi
  • Pool is good
  • Great pool
  • Wonderful swimming pool
  • Nice pool
  • 3 star Rural hotel
From$68
Very Good 4.0 /5Review Score Call
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