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

The George Washington Hotel a Wyndham Grand Hotel 103 East Piccadilly St, Winchester, VA 22601
  • Has swimming pool
  • 3-star property
  • Gym / Fitness Center Available
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Excellent 9.4 /10 Reviews Call BookMore Details
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Spark by Hilton Winchester 150 Wingate Dr, Winchester, VA 22601
  • We have a pool
  • 3 star property
  • Gym is available on property
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Excellent 9.2 /10 Recent Reviews Call BookMore Details
Hilton Garden Inn Winchester 120 Wingate Drive, Winchester, VA 22601
  • Includes a pool: Swimming pool, Pool hoist on site, Wheelchair-accessible pool. Pool access available from 10:00 AM to 10 PM.
  • Midscale hotel
  • Gym / Fitness Center Available
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Excellent 9.0 /10 Hotel Reviews Call BookMore Details
Hampton Inn Winchester-University / Mall Area 640 East Jubal Early Drive, Winchester, VA 22601
  • Pool in hotel: Pool hoist on site, Wheelchair-accessible pool, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from May 30 to September 05.
  • 3-star property
  • Check in: 3:00 PM
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Excellent 9.0 /10 Guest Reviews Call BookMore Details
Clarion Inn & Conference Center 711 Millwood Avenue, Winchester, VA 22601
  • Has swimming pool
  • Two star hotel
  • Check in: 3:00 PM
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Fairfield Inn & Suites by Marriott Winchester 250 Front Royal Pike, Winchester, VA 22601
  • Has swimming pool: Wheelchair-accessible pool.
  • 3 star hotel
  • Hotel has 3 floors
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Excellent 9.2 /10 Recent Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Winchester 1055 Millwood Pike Route 50 East, Winchester, VA 22602
  • Has swimming pool: Pool hoist on site, Wheelchair-accessible pool.
  • Three Star hotel
  • Gym is available on property
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Excellent 9.2 /10 Latest Reviews Call BookMore Details
Hampton Inn Winchester N / Conference Center VA 1204 Berryville Avenue, Winchester, VA 22601
  • Pool details: Pool hoist on site, Wheelchair-accessible pool, Outdoor seasonal pool. The seasonal pool will be open from May to August.
  • Three Star hotel
  • Pets Welcome
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Excellent 9.2 /10 Review Score Call BookMore Details
APM Inn & Suites 1347 Berryville Ave, Winchester, VA 22601
  • Has swimming pool
  • Economical property
  • Check-in time: 3:00 PM - 10:00 PM
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Average 7.0 /10 Review Score Call BookMore Details
Sleep Inn & Suites Winchester near University 140 Costello Dr, Winchester, VA 22602
  • Pool in hotel: Pool hoist on site, Wheelchair-accessible pool.
  • 3 star hotel
  • Hotel has 4 floors
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Average 7.6 /10 Hotel Reviews Call BookMore Details
Holiday Inn Winchester Se-Historic Gateway by IHG 333 Front Royal Pike, Winchester, VA 22602
  • Has swimming pool: Wheelchair-accessible pool.
  • 3 star property
  • Hotel has an eco-friendly policy Read more
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Excellent 9.0 /10 Latest Reviews Call BookMore Details
Home2 Suites by Hilton Winchester 240 Crossover Blvd, Winchester, VA 22601
  • Pool in hotel
  • Three Star hotel
  • Check-in time: 15:00:00
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Excellent 9.4 /10 Recent Reviews Call BookMore Details
TownePlace Suites by Marriott Winchester 170 Getty Ln, Winchester, VA 22603
  • Includes a pool: Swimming pool, Wheelchair-accessible pool. Pool access available from 6 AM to 10 PM.
  • 3-star property
  • Hotel has 4 floors
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Very Good 8.8 /10 Review Score Call BookMore Details
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Courtyard by Marriott Winchester 300 Marriott Drive, Winchester, VA 22603
  • Pool available: Swimming pool, Wheelchair-accessible pool. Pool access available from 7:00 AM to 11 PM.
  • 3-star property
  • Fitness center on property
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Excellent 9.0 /10 Read Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites Winchester by IHG 142 Foxridge Ln, Winchester, VA 22603
  • Has swimming pool: Pool access available from 9:00 AM to 10:00 PM.
  • Midscale hotel
  • Hotel has 3 floors
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Excellent 9.0 /10 Hotel Reviews Call BookMore Details
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Microtel Inn & Suites by Wyndham Winchester 150 Faraday Plaza, Winchester, VA 22603
  • Pool available: Pool hoist on site, Wheelchair-accessible pool. Pool access available from 7:00 AM to 11:00 PM.
  • Mid-scale property
  • Fitness + Health Center
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Very Good 8.7 /10 Reviews Call BookMore Details
Quality Inn Winchester 1601 Martinsburg Pike, Winchester, VA 22603
  • Includes a pool: Outdoor seasonal pool. The seasonal pool will be open from May to September.
  • 3 star property
  • 2 floors in property
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Excellent 9.4 /10 Guest Reviews Call BookMore Details
TRU by Hilton Winchester 118 Mercedes Court, Winchester, VA 22603
  • Includes a pool: Wheelchair-accessible pool.
  • Mid-scale property
  • Pets Welcome
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Excellent 9.2 /10 Reviews Call BookMore Details
SpringHill Suites by Marriott Winchester 280 MARKET STREET, Winchester, VA 22603
  • Pool details: Wheelchair-accessible pool.
  • Affordable property
  • Hotel has a green policy Learn more
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Excellent 9.4 /10 Hotel Reviews Call BookMore Details
Country Inn & Suites by Radisson Winchester, VA 141 Kernstown Commons Blvd, Winchester, VA 22602
  • Our hotel comes with a pool
  • Three Star hotel
  • Fitness / Gym is on-site
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Very Good 8.8 /10 Reviews Call BookMore Details
Quality Inn Stephens City - Winchester South 167 Town Run Ln, Stephens City, VA 22655 ~7.30 miles south of Winchester
  • Has swimming pool
  • 3-star hotel
  • Pets are Allowed
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Very Good 8.0 /10 Review Score Call BookMore Details
Holiday Inn Express Winchester South-Stephens City by IHG 165 Town Run Ln, Stephens City, VA 22655 ~7.33 miles south of Winchester
  • Has swimming pool: Wheelchair-accessible pool, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from June to September. Pool access available from 9 AM to 10 PM.
  • 3 star property
  • 3 floors in hotel
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Very Good 8.2 /10 Latest Reviews Call BookMore Details
LAuberge Provencale Inn & Restaurant 13630 Lord Fairfax Hwy, Boyce, VA 22663 ~8.39 miles southeast of Winchester
  • Pool in hotel: Pool umbrellas, Outdoor seasonal pool, Pool sun loungers, Access to nearby outdoor pool. The seasonal pool will be open from August to October. Pool access available from 8:00 AM to 8:00 PM.
  • High end property
  • 14 rooms in hotel
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Excellent 9.8 /10 Reviews Call BookMore Details
Econo Lodge Inn & Suites Middletown - Winchester South 91 Reliance Road, Middletown, VA 22645 ~11.62 miles southwest of Winchester
  • With a pool!
  • Economical hotel
  • 3 floors in property
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Poor 5.8 /10 Read Reviews Call BookMore Details
DoubleTree by Hilton Front Royal Blue Ridge Shadows 111 Hospitality Drive, Front Royal, VA 22630 ~13.19 miles south of Winchester
  • Pool details: Wheelchair-accessible pool. Pool access available from 7:00 AM to 10:00 PM.
  • Four-star hotel
  • Check-in time: 3:00 PM - midnight
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Excellent 9.0 /10 Recent Reviews Call BookMore Details
Hampton Inn Martinsburg South-Inwood 4758 Gerrardstown Road, Inwood, WV 25428 ~14.25 miles northeast of Winchester
  • Has swimming pool: Wheelchair-accessible pool, Outdoor seasonal pool, Pool sun loungers, Fence around pool. The seasonal pool will be open from May to September.
  • 3 star property
  • Pets are OK
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Excellent 9.2 /10 Latest Reviews Call BookMore Details
TownePlace Suites by Marriott Front Royal 5 Caroline Drive, Front Royal, VA 22630 ~14.70 miles south of Winchester
  • Includes a pool: Wheelchair-accessible pool, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from June to August. Pool access available from 7:00 AM to 10:00 PM.
  • 3-star hotel
  • Pet-friendly
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Excellent 9.6 /10 Review Score Call BookMore Details
Fairfield Inn & Suites Strasburg Shenandoah Valley 33760 Old Valley Pike, Strasburg, VA 22657 ~15.11 miles southwest of Winchester
  • Pool details: Wheelchair-accessible pool. Pool access available from 6 AM to 11 PM.
  • 3 star property
  • Fitness center on property
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Excellent 9.0 /10 Guest Reviews Call BookMore Details
Hampton Inn Front Royal 9800 Winchester Rd, Front Royal, VA 22630 ~15.13 miles south of Winchester
  • Pool available: Swimming pool, Pool hoist on site, Wheelchair-accessible pool.
  • 3-star property
  • Free breakfast
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Very Good 8.6 /10 Reviews Call BookMore Details
Twi-Lite Inn 53 West 14th Street, Front Royal, VA 22630 ~16.82 miles south of Winchester
  • Has swimming pool: Outdoor seasonal pool. The seasonal pool will be open from May 30 to September 05.
  • Two star Motel property
  • 20 rooms in property
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Very Good 8.2 /10 Read Reviews Call BookMore Details
Baymont by Wyndham Front Royal Near Shenandoah National Park 10 South Commerce Ave, Front Royal, VA 22630 ~18.07 miles south of Winchester
  • Pool details: Pool umbrellas, Swimming pool, Wheelchair-accessible pool, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from May to September. Pool access available from 10:00 AM to 10:00 PM.
  • 3-star hotel
  • 5 suites in hotel
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Average 6.4 /10 Hotel Reviews Call BookMore Details
Home2 Suites by Hilton Charles Town 70 Jefferson Crossing Way, Charles Town, WV 25414 ~19.25 miles east of Winchester
  • Has swimming pool: Swimming pool, Wheelchair-accessible pool. Pool access available from 8:00 AM to 11:00 PM.
  • Mid-scale hotel
  • Pets are Allowed
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Excellent 9.6 /10 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Charles Town 157 Pimlico Dr, Charles Town, WV 25414 ~19.34 miles east of Winchester
  • Has swimming pool: Wheelchair-accessible pool. Pool access available from 8 AM to 11 PM.
  • Affordable hotel
  • 131 rooms in property
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Excellent 9.4 /10 Reviews Call BookMore Details
Holiday Inn Express Charles Town by IHG 681 Flowing Springs Rd, Charles Town, WV 25438 ~19.43 miles east of Winchester
  • Has swimming pool: Pool hoist on site, Wheelchair-accessible pool. Pool access available from 7 AM to 11 PM.
  • Affordable property
  • Free complimentary breakfast
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Excellent 9.2 /10 Recent Reviews Call BookMore Details
Hilton Garden Inn Martinsburg 65 Priority Drive, Martinsburg, WV 25401 ~20.42 miles northeast of Winchester
  • Pool in hotel: Wheelchair-accessible pool.
  • 3-star hotel
  • Hotel has 14 suites
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Excellent 9.4 /10 Review Score Call BookMore Details
Quality Inn & Suites 1937 Short Road, Kearneysville, WV 25430 ~20.59 miles northeast of Winchester
  • Pool details: Outdoor seasonal pool. The seasonal pool will be open from July to September. Pool access available from 10 AM to 10:00 PM.
  • Midscale hotel
  • 71 suites in hotel
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Average 7.2 /10 Review Score Call BookMore Details
Home2 Suites by Hilton Martinsburg WV 820 FOXCROFT AVENUE, Martinsburg, WV 25401 ~21.26 miles northeast of Winchester
  • Pool available: Wheelchair-accessible pool.
  • Midscale hotel
  • Free breakfast
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Excellent 9.8 /10 Reviews Call BookMore Details
Hampton Inn Martinsburg 975 Foxcroft Ave, Martinsburg, WV 25401 ~21.41 miles northeast of Winchester
  • Includes a pool: Wheelchair-accessible pool, Outdoor seasonal pool. The seasonal pool will be open from May to September.
  • Mid-scale hotel
  • 99 rooms in hotel
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Very Good 8.8 /10 Hotel Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Martinsburg 451 Foxcroft Avenue, Martinsburg, WV 25401 ~21.68 miles northeast of Winchester
  • Pool in hotel: Pool umbrellas, Wheelchair-accessible pool, Outdoor seasonal pool, Pool sun loungers, Fence around pool. The seasonal pool will be open from May to September.
  • Three Star property
  • Hotel has 4 floors
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Very Good 8.8 /10 Reviews Call BookMore Details
Holiday Inn Martinsburg by IHG 301 Foxcroft Avenue, Martinsburg, WV 25401 ~21.71 miles northeast of Winchester
  • Pool available: Wheelchair-accessible pool, Pool sun loungers.
  • Three Star property
  • 120 sleeping rooms in hotel
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Excellent 9.0 /10 Review Score Call BookMore Details
Clarion Inn Harpers Ferry - Charles Town 4328 William L Wilson Fwy, Harpers Ferry, WV 25425 ~23.55 miles east of Winchester
  • Includes a swimming pool
  • Affordable hotel
  • 6 suites in hotel
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Average 7.8 /10 Recent Reviews Call BookMore Details
Comfort Inn Aikens Center 1872 Edwin Miller Blvd, Martinsburg, WV 25401 ~24.21 miles northeast of Winchester
  • Has swimming pool: Pool hoist on site, Wheelchair-accessible pool, Outdoor seasonal pool. The seasonal pool will be open from May to September.
  • Affordable property
  • 109 rooms in hotel
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Very Good 8.5 /10 Latest Reviews Call BookMore Details
Rodeway Inn 94 McMillan Court, Martinsburg, West Virginia 25401 ~24.24 miles northeast of Winchester
  • Includes a swimming pool
  • Three Star property
  • Check in: 16:00:00
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Average 6.5 /10 Guest Reviews Call BookMore Details
Goodstone Inn & Restaurant 36205 Snake Hill Road, Middleburg, VA 20117 ~25.41 miles southeast of Winchester
  • Has swimming pool: Outdoor seasonal pool, Pool sun loungers, Fence around pool. The seasonal pool will be open from May to October. Pool access available from 9:00 AM to 8:00 PM.
  • 4-star hotel
  • Hotel has 3 floors
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Clarion Hotel & Conference Center 233 Lowe Drive, Shepherdstown, WV 25443 ~25.48 miles northeast of Winchester
  • With a pool!
  • Cheap hotel
  • Check in: 4:00 PM
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Bavarian Inn Resort & Brewing Company 164 Shepherd Grade Rd, Shepherdstown, WV 25443 ~26.33 miles northeast of Winchester
  • Has swimming pool
  • 3-star Resort hotel
  • Check-in time: 4:00 PM - anytime
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Bavarian Inn 164 Shepherd Grade Road, Shepherdstown, WV 25443 ~26.34 miles northeast of Winchester
  • Pool in hotel
  • 3-star property
  • Check in: 16:00:00
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Very Good 8.2 /10 Latest Reviews Call BookMore Details
Salamander Resort & Spa 500 North Pendleton Street, Middleburg, VA 20117 ~26.76 miles southeast of Winchester
  • Pool available: Pool umbrellas, Billiards or pool table, Outdoor seasonal pool, Children's pool, Free pool cabanas. The seasonal pool will be open from April to October.
  • Luxury Five Star Resort hotel
  • Check-in: 4:00 PM - 12:30 AM
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Excellent 9.5 /10 Latest Reviews Call BookMore Details
Coolfont Resort 3621 Cold Run Valley Rd, Berkeley Springs, WV 25411 ~28.13 miles north of Winchester
  • Has a pool!
  • Economical Resort hotel
  • Check-in time: 3:00 PM - 8:00 PM
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Very Good 8.8 /10 Read Reviews Call BookMore Details
Comfort Inn Woodstock Shenandoah 1011 Motel Dr, Woodstock, VA 22664 ~28.55 miles southwest of Winchester
  • Includes a pool: Wheelchair-accessible pool, Outdoor seasonal pool. The seasonal pool will be open from May 24 to September 07.
  • Midscale property
  • Comp. Breakfast
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