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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
  • Midscale Suburban hotel
Quality Inn Skyline Drive in Front Royal
+1-800-230-4134
10 South Commerce Ave., Front Royal, VA 22630 ~16.71 miles west of Upperville
  • Pool available: Outdoor poolOpen 10:00 a.m. to 10:00 p.m. End of May to First of September
  • 2-star Downtown hotel
Aloft Winchester - Winchester 1055 Millwood Pike, Winchester, VA 22602 ~18.29 miles northwest of Upperville
  • Pool available: Splash, our Indoor Pool is open 6am-11pm
  • Affordable Suburban property
From$70
Very Good 4.0 /5Read Reviews Call
Sleep Inn & Suites in Winchester 140 Costello Dr., Winchester, VA 22602 ~18.37 miles northwest of Upperville
  • Includes a pool: 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.
  • Low-priced Suburban hotel
From$60
Very Good 4.0 /5Review Score Call
Holiday Inn Winchester Se Historic Gateway - Winchester 333 Front Royal Pike, Winchester, VA 22602 ~18.46 miles northwest of Upperville
  • With a pool!
  • Three Star Suburban property
From$83
Very Good 4.5 /5Review Score 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
  • 3-star Suburban hotel
From$72
Very Good 4.0 /5Reviews Call
Comfort Inn Stephens City 167 Town Run Lane, Stephens City, VA 22655 ~18.49 miles west of Upperville
  • Has swimming pool: The outdoor seasonal pool is open from 9:00am to 9:00pm
  • Mid-scale Highway property
Holiday Inn Express Winchester South / Stephens Ci - Stephens City 165 Town Run Lane, Stephens City, VA 22655 ~18.50 miles west of Upperville
  • Has a pool!
  • Affordable Rural property
Travelodge Winchester 160 Front Royal Pike, Winchester, VA 22602 ~18.54 miles northwest of Upperville
  • Pool details: 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.
  • 2 star Suburban hotel
Country Inn & Suites by Carlson Winchester Va : 141 Kernstown Commons Blvd. 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)
  • Mid-scale Mountain property
From$72
Very Good 4.5 /5Review Score Call
Towneplace Suites by Marriott Winchester in Winchester 170 Getty Ln, Winchester, VA 22603 ~18.77 miles northwest of Upperville
  • We have a pool ready for use
  • 3-star Suburban property
Best Western Lee Jackson Inn - Winchester 711 Millwood Ave., Winchester, VA 22601 ~18.78 miles northwest of Upperville
  • Pool available: Labor day to Memorial DayOutdoor
  • Cheap Highway hotel
From$49
Very Good 4.0 /5Review Score Call
Hampton Inn Winchester University / Mall Area 640 East Jubal Early Dr., Winchester, VA 22601 ~18.96 miles northwest of Upperville
  • Has swimming pool: Seasonal Outdoor Pool that is open from 8 am to 10 pm
  • Mid-scale Highway property
From$60
Very Good 4.5 /5Read Reviews Call
Baymont Inn & Suites - Warrenton 7379 Comfort Inn Dr., Warrenton, VA 20187 ~18.97 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.
  • 2 star Suburban property
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.
  • Midscale Highway property
Wingate by Wyndham : 150 Wingate Dr.
+1-800-230-4134
150 Wingate Dr., Winchester, VA 22601 ~19.15 miles northwest of Upperville
  • Pool in hotel
  • Midscale Downtown hotel
Hilton Garden Inn 120 Wingate Dr., Winchester, VA 22601 ~19.21 miles northwest of Upperville
  • Includes a pool: Indoor Pool and Whirlpool. Open 5AM - 10PM.
  • Affordable Highway hotel
Holiday Inn Express Hotel & Suites - Warrenton 410 Holiday Court, Warrenton, VA 20186 ~19.44 miles south of Upperville
  • Includes a pool: We have an outdoor, seasonal pool that is open between Labor Day and Memorial Day, between the hours of 8:00am and 10:00pm.
  • 3 star Suburban property
From$88
Very Good 4.0 /5Read Reviews Call
Comfort Suites Leesburg - Leesburg 80 Prosperity Ave., Leesburg, VA 20175 ~19.93 miles east of Upperville
  • Pool available: Indoor Heated Pool with whirlpool. Outdoor patio connects to indoor pool, sun chairs available on the patio.
  • Three Star hotel
Best Western Leesburg Hotel : 726 East Market St. 726 East Market St., Leesburg, VA 20176 ~20.03 miles east of Upperville
  • Includes a pool: Seasonal Pool open Memorial Day to Labor Day weather permitting
  • 3-star Suburban property
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
  • Mid-scale Downtown hotel
Hampton Inn & Suites Leesburg Va 117 Fort Evans Rd. Ne, Leesburg, VA 20176 ~20.26 miles east of Upperville
  • Pool in hotel: Indoor Heated Pool524 square feet 3-5ft DeepOpen 6am-10pm
  • Inexpensive Suburban property
Hampton Inn Gainesville / Haymarket 7300 Atlas Walk Way, Gainesville, VA 20155 ~20.29 miles southeast of Upperville
  • Includes a pool
  • 3-star Rural property
Comfort Inn : 1601 Martinsburg Pike
+1-800-997-5148
1601 Martinsburg Pike, Winchester, VA 22603 ~20.59 miles northwest of Upperville
  • Has a pool!
  • Two star Highway hotel
Clarion Inn Leesburg 1500 East Market St., Leesburg, VA 20176 ~20.86 miles east of Upperville
  • Pool available: Large outdoor pool. Private and intimate seating areas on porches and verandas.9am-10pm Memorial Day to Labor Day
  • Affordable Highway hotel
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