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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
  • Pool available: We have an indoor pool which is open from 8am-10pm
  • Three Star Suburban property
From$89
Very Good 4.5 /5Review Score Call
Quality Inn Skyline Drive
+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
  • Two star Downtown property
Aloft Winchester in Winchester 1055 Millwood Pike, Winchester, VA 22602 ~18.29 miles northwest of Upperville
  • Pool details: Splash, our Indoor Pool is open 6am-11pm
  • 3 star Suburban hotel
From$105
Very Good 4.0 /5Read Reviews Call
Sleep Inn & Suites 140 Costello Dr., Winchester, VA 22602 ~18.37 miles northwest of Upperville
  • Has swimming 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 Cost Suburban hotel
Holiday Inn Winchester Se Historic Gateway in Winchester 333 Front Royal Pike, Winchester, VA 22602 ~18.46 miles northwest of Upperville
  • Includes a pool
  • 3 star Suburban property
Fairfield & Suites by Marriott Winchester - Winchester
+1-800-881-1523
250 Front Royal Pike, Winchester, VA 22601 ~18.46 miles northwest of Upperville
  • Includes a pool: Indoor pool open daily from 9:00AM - 10:00PM
  • Three Star Suburban property
From$72
Very Good 4.0 /5Read Reviews Call
Comfort Inn Stephens City 167 Town Run Lane, Stephens City, VA 22655 ~18.49 miles west of Upperville
  • Pool in hotel: The outdoor seasonal pool is open from 9:00am to 9:00pm
  • Midscale 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
  • We have a pool
  • 3-star Rural property
From$60
Very Good 4.0 /5Reviews Call
Travelodge Winchester in 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.
  • Two-star Suburban property
Country Inn & Suites by Carlson Winchester Va 141 Kernstown Commons Blvd., Winchester, VA 22602 ~18.58 miles west of Upperville
  • Includes a pool: Indoor heated pool & hot tub open daily from 6am-12am (midnight)
  • Affordable Mountain property
Towneplace Suites by Marriott Winchester 170 Getty Ln, Winchester, VA 22603 ~18.77 miles northwest of Upperville
  • Pool in hotel
  • 3 star Suburban hotel
Best Western Lee Jackson Inn : 711 Millwood Ave. 711 Millwood Ave., Winchester, VA 22601 ~18.78 miles northwest of Upperville
  • Pool details: Labor day to Memorial DayOutdoor
  • 2 star Highway hotel
From$49
Very Good 4.0 /5Reviews Call
Hampton Inn Winchester University / Mall Area - Winchester 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
  • Midscale Highway property
From$60
Very Good 4.5 /5Read Reviews Call
Baymont Inn & Suites : 7379 Comfort Inn Dr. 7379 Comfort Inn Dr., Warrenton, VA 20187 ~18.97 miles south of Upperville
  • Includes a pool: 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.
  • Low priced 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.
  • Affordable Highway property
From$50
Very Good 4.5 /5Review Score Call
Wingate by Wyndham : 150 Wingate Dr.
+1-800-230-4134
150 Wingate Dr., Winchester, VA 22601 ~19.15 miles northwest of Upperville
  • Our hotel comes with a pool
  • Affordable Downtown property
From$95
Very Good 4.0 /5Reviews Call
Hilton Garden Inn - Winchester 120 Wingate Dr., Winchester, VA 22601 ~19.21 miles northwest of Upperville
  • Includes a pool: Indoor Pool and Whirlpool. Open 5AM - 10PM.
  • 3-star Highway property
From$89
Very Good 4.5 /5Read Reviews Call
Holiday Inn Express Hotel & Suites - Warrenton 410 Holiday Court, Warrenton, VA 20186 ~19.44 miles south of Upperville
  • Pool in hotel: We have an outdoor, seasonal pool that is open between Labor Day and Memorial Day, between the hours of 8:00am and 10:00pm.
  • Midscale Suburban property
Comfort Suites Leesburg - Leesburg 80 Prosperity Ave., Leesburg, VA 20175 ~19.93 miles east of Upperville
  • Pool details: Indoor Heated Pool with whirlpool. Outdoor patio connects to indoor pool, sun chairs available on the patio.
  • Affordable property
From$99
Very Good 4.5 /5Reviews Call
Best Western Leesburg Hotel 726 East Market St., Leesburg, VA 20176 ~20.03 miles east of Upperville
  • Includes a pool: Seasonal outdoor swimming pool open Memorial Day to Labor Day (pool may be opened earlier than Memorial Day and stay open beyond Labor Day if weather allows).
  • Three Star Suburban hotel
Homewood Suites by Hilton Leesburg Va 115 Fort Evans Rd. Ne, Leesburg, VA 20176 ~20.25 miles east of Upperville
  • Has swimming pool: 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 in hotel: Indoor Heated Pool524 square feet 3-5ft DeepOpen 6am-10pm
  • Two-star Suburban property
Hampton Inn Gainesville / Haymarket - Gainesville 7300 Atlas Walk Way, Gainesville, VA 20155 ~20.29 miles southeast of Upperville
  • Includes a pool
  • Three 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 swimming pool
  • Low Cost Highway property
From$65
Very Good 4.0 /5Reviews Call
Clarion Inn Leesburg : 1500 East Market St. 1500 East Market St., Leesburg, VA 20176 ~20.86 miles east of Upperville
  • Includes a pool: Large outdoor pool. Private and intimate seating areas on porches and verandas.9am-10pm Memorial Day to Labor Day
  • 3 star Highway hotel
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