Winchester Hotels with Pools - Outdoor/Indoor Pools in Winchester VA

Winchester hotels and motels with swimming pools that are perfect for a family are listed below. Search for cheap and discount hotel rates at hotels with a pool in or near Winchester, VA for your upcoming individual or family vacation. We list the best pool equipped, kid friendly Winchester Virginia hotel and motel rooms for children. Review the list of Winchester hotels with indoor or outdoor pools below to find the perfect lodging for you and your kids.
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Winchester Hotels with Outdoor or Indoor Pools

Hampton Inn Winchester University / Mall Area in Winchester 640 East Jubal Early Dr., Winchester, VA 22601 Call
  • Pool in hotel: Seasonal Outdoor Pool that is open from 8 am to 10 pm
  • 3 star Highway property
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From$98 total
Very good 4.0 /5 Latest Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Winchester in Winchester 1055 Millwood Pike, Winchester, VA 22602 Call
  • Has swimming pool: Our Indoor Pool is open 7am-10pm
  • Three Star Suburban property
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From$96 total
Very good 4.0 /5 Reviews Call BookMore Details
Fairfield & Suites by Marriott Winchester 250 Front Royal Pike, Winchester, VA 22602 Call
  • Has swimming pool: Indoor pool open daily from 9:00AM - 10:00PM
  • 3-star Rural hotel
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From$84 total
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Sleep Inn & Suites Winchester Near University 140 Costello Dr., Winchester, VA 22602 Call
  • 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.
  • 2 star Suburban hotel
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From$72 total
Very good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Winchester Se Historic Gateway by IHG 333 Front Royal Pike, Winchester, VA 22602 Call
  • Pool details: Indoor
  • Three Star Suburban hotel
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From$82 total
Very good 4.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express & Suites : 142 Fox Ridge Lane 142 Fox Ridge Lane, Winchester, VA 22603 Call
  • Has swimming pool: Indoor Heated Pool with Jacuzzi- Open 9am-10pm daily
  • Affordable Rural property
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From$90 total
Very good 4.0 /5 Reviews Call BookMore Details
Quality Inn Winchester 1601 Martinsburg Pike, Winchester, VA 22603 Call
  • Pool available: Our Seasonal Outdoor Pool hours are 9AM-10PM.
  • Two-star Highway hotel
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From$92 total
Very good 4.0 /5 Latest Reviews Call BookMore Details
Country Inn & Suites by Radisson Winchester Va in Winchester 141 Kernstown Commons Blvd., Winchester, VA 22602 Call
  • Pool details: Indoor heated pool & hot tub open daily from 6am-12am (midnight)
  • 3-star Suburban property
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From$96 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
The George Washington a Wyndham Grand Hotel : 103 East Piccadilly St. 103 East Piccadilly St., Winchester, VA 22601 Call
  • Our hotel comes with a pool
  • Three Star Downtown property
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From$118 total
Very good 4.0 /5 Guest Reviews Call BookMore Details
Towneplace Suites by Marriott Winchester 170 Getty Ln, Winchester, VA 22603 Call
  • We have a pool
  • Midscale Suburban property
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From$88 total
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Winchester South Stephens City by IHG 165 Town Run Ln, Stephens City, VA 22655 Call ~7.28 miles south of Winchester
  • Has a pool!
  • Three Star Rural property
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From$81 total
Very good 4.0 /5 Recent Reviews Call BookMore Details
Quality Inn Stephens City - Winchester South - Stephens City 167 Town Run Lane, Stephens City, VA 22655 Call ~7.30 miles south of Winchester
  • Pool details: The outdoor seasonal pool is open from 9:00am to 9:00pm
  • Three Star Highway property
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From$72 total
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Front Royal : 9800 Winchester Rd. 9800 Winchester Rd., Front Royal, VA 22630 Call ~15.32 miles south of Winchester
  • Includes a pool: We have an indoor pool which is open from 8am-10pm
  • 3-star Suburban property
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From$128 total
Very good 4.0 /5 Read Reviews Call BookMore Details
Ramada by Wyndham Strasburg : 21 Signal Knob Dr. 21 Signal Knob Dr., Strasburg, VA 22657 Call ~15.50 miles southwest of Winchester
  • Has swimming pool
  • Economical Rural hotel
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From$75 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Charles Town by IHG : 681 Flowing Springs Rd. 681 Flowing Springs Rd., Ranson, WV 25438 Call ~19.37 miles east of Winchester
  • Pool available: Outdoor, seasonal
  • Midscale Mountain property
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From$96 total
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Quality Inn & Suites - Kearneysville 1937 Short Rd., Kearneysville, WV 25430 Call ~20.55 miles northeast of Winchester
  • Includes a pool: Outdoor pool 10:00 am to 11:00PM.
  • Affordable property
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From$66 total
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn Martinsburg - Martinsburg 975 Foxcroft Ave., Martinsburg, WV 25401 Call ~20.84 miles northeast of Winchester
  • Pool available: Outdoor pool. Opens Memorial Weekend and closes after Labor Day. Hours: 9 AM to 10 PM
  • 3 star Highway property
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From$96 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Martinsburg 301 Foxroft Ave., Martinsburg, WV 25401 Call ~21.70 miles northeast of Winchester
  • Pool available: The indoor pool is open from 6:00am-11:00pm daily.
  • 3 star Suburban property
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From$133 total
Very good 4.0 /5 Recent Reviews Call BookMore Details
Clarion Inn Harpers Ferry Charles Town in Harpers Ferry 4328 William L Wilson Fwy, Harpers Ferry, WV 25425 Call ~23.42 miles east of Winchester
  • Pool details: 10am-10pm indoor
  • Affordable Mountain hotel
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From$86 total
Very good 4.0 /5 Guest Reviews Call BookMore Details
Salamander Resort And Spa : 500 North Pendelton St. 500 North Pendelton St., Middleburg, VA 20117 Call ~26.68 miles southeast of Winchester
  • Pool details: Chill out. Cool off. Immerse yourself in the great outdoors. This is what summer is all about. Welcome to Splash Pool & Cafe, Salamander Resort & Spa’s new reprieve tucked away in the Virginia countryside. Bring the shades. Lather on the sunscreen. Settle into a comfy lounge chair with a specialty drink and your favorite summer read. At Splash Pool & Cafe, relaxation is key. The intimate surroundings make it easy to lay back and soak up some glorious sunshine. When the sun begins to notch up the temperature, there’s plenty of ways to keep cool. Take a comfortable swim in the pool or make your way over to the two cascading water features where kids (big and small) will undoubtedly find refreshing jets of shooting water endlessly entertaining. Throughout the day, the Splash team will be on hand to offer delicious complimentary frozen berries, grapes and other summer amenities including free sunglass polishing and Evian face misting. Memorial Day through Labor Day Friday & Saturday: 10:00 a.m. - 8:00 p.m.
  • Luxurious 5 Star Resort property
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From$346 total
Very good 4.0 /5 Recent Reviews Call BookMore Details
Hampton Inn & Suites - Woodstock 1150 Motel Dr., Woodstock, VA 22664 Call ~28.86 miles southwest of Winchester
  • Has swimming pool
  • 3 star Highway property
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From$96 total
Average 3.0 /5 Read Reviews Call BookMore Details
SureStay Plus by Best Western Berkeley Springs - Berkeley Springs 1776 Valley Rd., Berkeley Springs, WV 25411 Call ~29.70 miles north of Winchester
  • With a pool!
  • Affordable Resort property
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From$74 total
Very good 4.0 /5 Review Score Call BookMore Details
Holiday Inn Express & Suites Leesburg - Historic District by IHG - Leesburg 80 Prosperity Ave., Leesburg, VA 20175 Call ~33.44 miles east of Winchester
  • Pool details: Indoor Heated Pool with whirlpool. Outdoor patio connects to indoor pool, sun chairs available on the patio.
  • Mid-scale hotel
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From$130 total
Very good 4.0 /5 Guest Reviews Call BookMore Details
Homewood Suites by Hilton Leesburg Va 115 Fort Evans Rd. Ne, Leesburg, VA 20176 Call ~33.68 miles east of Winchester
  • Pool in hotel: Outdoor Pool Open from 8:00 AM to 10:00 PM Pool open every year from Memorial Day to Labor Day
  • 3-star Downtown property
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From$142 total
Very good 4.0 /5 Read Reviews Call BookMore Details
Hampton Inn & Suites Leesburg 117 Fort Evans Rd. Ne, Leesburg, VA 20176 Call ~33.71 miles east of Winchester
  • Pool in hotel: Indoor Heated Pool 524 square feet 3-5ft Deep Open 6am-10pm
  • 3 star Suburban property
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From$96 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Carradoc Hall Hotel & Conference Center by The Red Collection in Leesburg 1500 East Market St., Leesburg, VA 20176 Call ~34.97 miles east of Winchester
  • Pool available: Very Large outdoor pool with Furniture to go all around
  • 3 star Suburban hotel
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From$90 total
Poor 2.0 /5 Guest Reviews Call BookMore Details
Country Inn & Suites Hagerstown Maryland 17612 Valley Mall Rd., Hagerstown, MD 21740 Call ~37.22 miles northeast of Winchester
  • Includes a pool: Indoor pool open daily until midnight.
  • Midscale Suburban property
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From$94 total
Very good 4.0 /5 Guest Reviews Call BookMore Details
Baymont Inn & Suites Warrenton 7379 Comfort Inn Dr., Warrenton, VA 20187 Call ~37.41 miles southeast of Winchester
  • 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.
  • Cheap Suburban property
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From$72 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Motel 6 Hagerstown, MD 11321 Massey Blvd., Hagerstown, MD 21740 Call ~37.50 miles northeast of Winchester
  • We have a pool ready for use
  • Cheap property
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From$72 total
Very good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express & Suites Hagerstown by IHG 241 Railway Ln, Hagerstown, MD 21740 Call ~37.56 miles northeast of Winchester
  • Pool available: Indoor Pool Location: Indoor Hours: 6:00 AM to 10:00 PM Heated pool Whirlpool
  • Midscale Highway property
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From$120 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Homewood Suites by Hilton Hagerstown 1650 Pullman Lane, Hagerstown, MD 21740 Call ~37.74 miles northeast of Winchester
  • Pool available: Pool open daily 6am -10pm-
  • Affordable Rural property
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From$136 total
Very good 4.0 /5 Read Reviews Call BookMore Details
Home2 Suites by Hilton Hagerstown - Hagerstown 1661 Pullman Lane, Hagerstown, MD 21740 Call ~37.74 miles northeast of Winchester
  • Pool details: Eco-friendly, chemical-free saline pool (indoor) 6:00am -10:00pm
  • Midscale Suburban hotel
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From$114 total
Very good 4.0 /5 Guest Reviews Call BookMore Details
Aloft by Marriott Dulles Airport North : 22390 Flagstaff Plaza 22390 Flagstaff Plaza, Ashburn, VA 20148 Call ~38.72 miles east of Winchester
  • Pool details: Indoor pool
  • Midscale Airport hotel
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From$96 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Springhill Suites by Marriott Ashburn Dulles North 20065 Lakeview Center Plaza, Ashburn, VA 20147 Call ~39.07 miles east of Winchester
  • Has swimming pool: Indoor pool open from 10am-10pm
  • Affordable Suburban property
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From$94 total
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Embassy Suites by Hilton Dulles North Loudoun 44610 Waxpool Rd., Ashburn, VA 20147 Call ~39.41 miles east of Winchester
  • Pool in hotel: Indoor/Outdoor Swimming pool
  • Four star Airport hotel
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From$150 total
Average 3.0 /5 Latest Reviews Call BookMore Details
Homewood Suites by Hilton Dulles North / Loudoun : 44620 Waxpool Rd. 44620 Waxpool Rd., Dulles, VA 20147 Call ~39.42 miles east of Winchester
  • Has swimming pool: Indoor/Outdoor Swimming pool
  • Affordable Airport hotel
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From$96 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Home 2 Chantilly 43340 Defender Dr., Chantilly, VA 20152 Call ~39.69 miles east of Winchester
  • Pool in hotel: • INDOOR SWIMMING POOL is available 6 AM to 10 PM
  • 4 star Airport property
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From$130 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn by Hilton Gainesville Haymarket in Gainesville 7300 Atlas Walk Way, Gainesville, VA 20155 Call ~39.93 miles southeast of Winchester
  • Includes a swimming pool
  • Midscale Rural property
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From$106 total
Very good 4.0 /5 Recent Reviews Call BookMore Details
DoubleTree by Hilton Sterling - Dulles Airport in Sterling 21611 Atlantic Blvd., Sterling, VA 20166 Call ~41.13 miles east of Winchester
  • Has swimming pool: Heated indoor pool and whirlpool spa open from 5am to 10pm daily.
  • Three Star Airport property
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From$70 total
Very good 4.0 /5 Reviews Call BookMore Details
Washington Dulles Airport Marriott : 45020 Aviation Dr. 45020 Aviation Dr., Dulles, VA 20166 Call ~41.34 miles east of Winchester
  • Pool available: Indoor Pool: Everday from 6AM to 10PM Outdoor Pool: Seasonal
  • 3 star Airport property
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From$96 total
Average 3.0 /5 Read Reviews Call BookMore Details
Springhill Suites by Marriott Dulles Airport in Sterling 22595 Shaw Rd., Sterling, VA 20166 Call ~41.52 miles east of Winchester
  • Pool in hotel: Our pool is open from 6am to 10pm daily. It is an indoor pool with a patio connected to go outside when the weather is nice.
  • Affordable Airport hotel
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From$96 total
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn Washington Dulles : 1000 Sully Rd. 1000 Sully Rd., Dulles, VA 20166 Call ~41.66 miles east of Winchester
  • Pool available: We have an indoor junior olympic size swimming pool. The Hours of Operation are 7:30 AM - 10 PM, Saturday 9:30 AM - 10:00PM, and Sunday 10:00AM - 6:00PM
  • Mid-scale Airport hotel
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From$94 total
Very good 4.0 /5 Reviews Call BookMore Details
Hyatt Place Sterling Dulles Airport North : 21481 Ridgetop Circle 21481 Ridgetop Circle, Sterling, VA 20166 Call ~41.90 miles east of Winchester
  • Pool details: Outdoor Pool
  • Mid-scale Airport hotel
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From$70 total
Very good 4.0 /5 Latest Reviews Call BookMore Details
Hyatt House Sterling Dulles Airport North 45520 Dulles Plaza, Sterling, VA 20166 Call ~41.99 miles east of Winchester
  • Pool in hotel: Outdoor seasonal pool open from 10:00 AM - 09:00 PM. 20'x40'. 5' in deepest.
  • Mid-scale Airport property
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From$96 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Best Western Historic Frederick 420 Prospect Blvd., Frederick, MD 21701 Call ~42.38 miles east of Winchester
  • Includes a pool: We have seasonal outdoor pool that is open from 8am until 10pm.
  • Economical Downtown hotel
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From$72 total
Average 3.0 /5 Latest Reviews Call BookMore Details
Hampton Inn Dulles - Cascades 46331 Mcclellan Way, Sterling, VA 20165 Call ~42.39 miles east of Winchester
  • Pool in hotel: 10am-10pm Medium Indoor Pool Max. depth 4 feet
  • Mid-scale Airport hotel
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From$78 total
Very good 4.5 /5 Reviews Call BookMore Details
Towneplace Suites by Marriott Frederick 5050 Westview Dr., Frederick, MD 21703 Call ~42.51 miles east of Winchester
  • We have a pool
  • Three Star property
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From$108 total
Very good 4.0 /5 Reviews Call BookMore Details
Hyatt Regency Dulles : 2300 Dulles Corner Blvd. 2300 Dulles Corner Blvd., Herndon, VA 20171 Call ~42.56 miles east of Winchester
  • Includes a pool: Open from 6a-10p, come enjoy our indoor pool with heated whirlpool.
  • 4 star Airport property
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From$90 total
Very good 4.0 /5 Latest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Frederick : 5220 Westview Dr. 5220 Westview Dr., Frederick, MD 21703 Call ~42.59 miles east of Winchester
  • We have a pool
  • 3 star Suburban property
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From$106 total
Very good 4.0 /5 Recent Reviews Call BookMore Details
Hampton Inn Washington-Dulles Int'l Airport South in Chantilly 4050 Westfax Dr., Chantilly, VA 20151 Call ~42.65 miles east of Winchester
  • We have a pool ready for use
  • Mid-scale Airport property
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From$96 total
Average 3.0 /5 Review Score Call BookMore Details
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