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Upperville Hotels with Outdoor or Indoor Pools

Hampton Inn in Front Royal +1-800-230-4134 9800 Winchester Rd., Front Royal, VA 22630 ~16.61 miles west of Upperville
  • Has a pool!
  • Mid-scale Suburban hotel
From$89
Very Good 4.5 /5 Read Reviews
Quality Inn Skyline Drive : 10 South Commerce Ave. +1-800-997-5148 10 South Commerce Ave., Front Royal, VA 22630 ~16.71 miles west of Upperville
  • Includes a pool: Outdoor pool Open 10:00 a.m. to 10:00 p.m. End of May to First of September
  • Economical Downtown property
From$58
Average 3.0 /5 Guest Reviews
Holiday Inn Hotel & Suites Front Royal Blue Ridge +1-888-205-8144 111 Hospitality Dr., Front Royal, VA 22630 ~17.37 miles west of Upperville
  • Pool in hotel: Heated Indoor Pool and Hot Tub 7:30am - 10:00 pm
  • Midscale Suburban property
From$83
Very Good 4.5 /5 Hotel Reviews
Sleep Inn & Suites : 140 Costello Dr. +1-800-997-5149 140 Costello Dr., Winchester, VA 22602 ~18.37 miles northwest of Upperville
  • Pool available: 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.
  • Economy Suburban property
From$60
Very Good 4.0 /5 Reviews
Holiday Inn Winchester Se Historic Gateway in Winchester +1-800-230-4134 333 Front Royal Pike, Winchester, VA 22602 ~18.46 miles northwest of Upperville
  • Has swimming pool
  • Midscale Suburban hotel
From$74
Very Good 4.5 /5 Recent Reviews
Fairfield & Suites by Marriott Winchester +1-800-997-5148 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
  • Mid-scale Suburban hotel
From$80
Very Good 4.0 /5 Latest Reviews
Holiday Inn Express Winchester South / Stephens Ci +1-888-205-8144 165 Town Run Lane, Stephens City, VA 22655 ~18.50 miles west of Upperville
  • Includes a swimming pool
  • Three Star Rural property
From$62
Very Good 4.0 /5 Read Reviews
Travelodge Winchester in Winchester +1-800-997-5149 160 Front Royal Pike, Winchester, VA 22602 ~18.54 miles northwest of Upperville
  • Includes a 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.
  • 2 star Suburban hotel
From$38
Average 3.0 /5 Review Score
Country Inn & Suites by Carlson Winchester Va in Winchester +1-800-230-4134 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)
  • Affordable Mountain property
From$72
Very Good 4.5 /5 Review Score
Best Western Lee Jackson Inn in Winchester +1-800-997-5148 711 Millwood Ave., Winchester, VA 22601 ~18.78 miles northwest of Upperville
  • Has swimming pool: Labor day to Memorial Day Outdoor
  • 2 star Highway hotel
From$49
Very Good 4.0 /5 Guest Reviews
Hampton Inn Winchester University / Mall Area - Winchester +1-888-205-8144 640 East Jubal Early Dr., Winchester, VA 22601 ~18.96 miles northwest of Upperville
  • Pool in hotel: Seasonal Outdoor Pool that is open from 8 am to 10 pm
  • 3-star Highway hotel
From$60
Very Good 4.0 /5 Recent Reviews
Baymont Inn & Suites : 7379 Comfort Inn Dr. +1-800-997-5149 7379 Comfort Inn Dr., Warrenton, VA 20187 ~18.97 miles south of Upperville
  • Pool available: 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.
  • Economy Suburban property
From$50
Poor 2.5 /5 Recent Reviews
Hampton Inn & Conference Center in Winchester +1-800-230-4134 1204 Berryville Ave., Winchester, VA 22601 ~18.98 miles northwest of Upperville
  • Includes a pool: 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$70
Very Good 4.5 /5 Latest Reviews
Wingate by Wyndham in Winchester +1-800-997-5148 150 Wingate Dr., Winchester, VA 22601 ~19.15 miles northwest of Upperville
  • Has swimming pool
  • Three Star Downtown property
From$78
Very Good 4.0 /5 Reviews
Hilton Garden Inn in Winchester +1-888-205-8144 120 Wingate Dr., Winchester, VA 22601 ~19.21 miles northwest of Upperville
  • Pool details: Indoor Pool and Whirlpool. Open 5AM - 10PM.
  • 3 star Highway hotel
From$83
Very Good 4.5 /5 Review Score
Holiday Inn Express Hotel & Suites +1-800-997-5149 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 hotel
From$85
Very Good 4.0 /5 Guest Reviews
Comfort Suites Leesburg +1-800-230-4134 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.
  • 3 star property
From$95
Very Good 4.5 /5 Guest Reviews
Best Western Leesburg Hotel - Leesburg +1-800-997-5148 726 East Market St., Leesburg, VA 20176 ~20.03 miles east of Upperville
  • Our hotel comes with a pool
  • 3 star Suburban property
From$80
Very Good 4.0 /5 Latest Reviews
Homewood Suites by Hilton Leesburg Va : 115 Fort Evans Rd. Ne +1-888-205-8144 115 Fort Evans Rd. Ne, Leesburg, VA 20176 ~20.25 miles east of Upperville
  • Pool in hotel: Outdoor Pool Open from 8:00 AM to 10:00 PM Pool open every year from Memorial Day to Labor Day
  • Three Star Downtown property
From$90
Very Good 4.5 /5 Reviews
Hampton Inn & Suites Leesburg Va : 117 Fort Evans Rd. Ne +1-800-997-5149 117 Fort Evans Rd. Ne, Leesburg, VA 20176 ~20.26 miles east of Upperville
  • Pool details: Indoor Heated Pool 524 square feet 3-5ft Deep Open 6am-10pm
  • 2 star Suburban hotel
From$84
Very Good 4.0 /5 Guest Reviews
Hampton Inn Gainesville / Haymarket +1-800-230-4134 7300 Atlas Walk Way, Gainesville, VA 20155 ~20.29 miles southeast of Upperville
  • We have a pool
  • Three Star Rural hotel
From$99
Very Good 4.5 /5 Hotel Reviews
Comfort Inn in Winchester +1-800-997-5148 1601 Martinsburg Pike, Winchester, VA 22603 ~20.59 miles northwest of Upperville
  • Includes a pool
  • Cheap Highway property
From$65
Very Good 4.5 /5 Review Score
Clarion Inn Leesburg +1-888-205-8144 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
  • Three Star Highway hotel
From$79
Average 3.5 /5 Hotel Reviews
Holiday Inn Express & Suites +1-800-997-5149 142 Fox Ridge Lane, Winchester, VA 22603 ~21.51 miles northwest of Upperville
  • Has swimming pool: 9am-10pm Indoor with Jacuzzi
  • Midscale Rural property
From$70
Very Good 4.0 /5 Read Reviews
Courtyard by Marriott Winchester Medical Center +1-800-230-4134 300 Marriott Dr., Winchester, VA 22603 ~21.74 miles northwest of Upperville
  • Pool details: Indoor Pool Hours are 6:00 am - 11:00 pm
  • Three Star Suburban hotel
From$89
Very Good 4.0 /5 Reviews
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