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

Upperville 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 Upperville, VA for your upcoming individual or family vacation. We list the best pool equipped, kid friendly Upperville Virginia hotel and motel rooms for children. Review the list of Upperville hotels with indoor or outdoor pools below to find the perfect lodging for you and your kids.

Upperville Hotels with Outdoor or Indoor Pools

Goodstone Inn & Restaurant 36205 Snake Hill Road, Middleburg, VA 20117 +1-888-389-4121 ~7.11 miles east of Upperville
  • 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 18 rooms
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Salamander Resort & Spa 500 North Pendleton Street, Middleburg, VA 20117 +1-888-675-2083 ~7.97 miles east of Upperville
  • Has swimming pool: 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
  • Fitness + Health Center
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Excellent 9.5 /10 Hotel Reviews Call BookMore Details
LAuberge Provencale Inn & Restaurant 13630 Lord Fairfax Hwy, Boyce, VA 22663 +1-800-716-8490 ~12.27 miles west of Upperville
  • Has swimming pool: 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.
  • 4-star hotel
  • 2 floors in hotel
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Excellent 9.8 /10 Review Score Call BookMore Details
DoubleTree by Hilton Front Royal Blue Ridge Shadows 111 Hospitality Drive, Front Royal, VA 22630 +1-800-805-5223 ~15.71 miles west of Upperville
  • Includes a pool: Wheelchair-accessible pool. Pool access available from 7:00 AM to 10:00 PM.
  • 4-star property
  • Hotel has 7 floors
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Excellent 9.0 /10 Review Score Call BookMore Details
TownePlace Suites by Marriott Front Royal 5 Caroline Drive, Front Royal, VA 22630 +1-888-965-1860 ~16.08 miles west of Upperville
  • Pool in hotel: 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.
  • Three Star property
  • Check in: 3:00 PM - 10:00 PM
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Excellent 9.6 /10 Latest Reviews Call BookMore Details
Hampton Inn Front Royal 9800 Winchester Rd, Front Royal, VA 22630 +1-888-788-5576 ~16.53 miles west of Upperville
  • Pool details: Swimming pool, Pool hoist on site, Wheelchair-accessible pool.
  • Three Star property
  • 9 suites in hotel
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Very Good 8.6 /10 Read Reviews Call BookMore Details
Baymont by Wyndham Front Royal Near Shenandoah National Park 10 South Commerce Ave, Front Royal, VA 22630 +1-888-897-9207 ~16.74 miles west of Upperville
  • Includes a pool: 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.
  • Mid-scale hotel
  • Complimentary breakfast is offered
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Average 6.4 /10 Guest Reviews Call BookMore Details
Twi-Lite Inn 53 West 14th Street, Front Royal, VA 22630 +1-888-311-4278 ~16.89 miles west of Upperville
  • Pool available: Outdoor seasonal pool. The seasonal pool will be open from May 30 to September 05.
  • Two-star Motel hotel
  • Check in: 3:00 PM - anytime
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Very Good 8.2 /10 Review Score Call BookMore Details
Airlie Hotel 6809 Airlie Road, Warrenton, VA 20187 +1-888-469-4795 ~16.93 miles south of Upperville
  • Has swimming pool: Swimming pool, Billiards or pool table, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from May 27 to September 01.
  • Midscale property
  • Access to gym on-site
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Very Good 8.6 /10 Review Score Call BookMore Details
La Quinta Inn & Suites by Wyndham Winchester 1055 Millwood Pike Route 50 East, Winchester, VA 22602 +1-888-734-9421 ~18.32 miles northwest of Upperville
  • Pool in hotel: Pool hoist on site, Wheelchair-accessible pool.
  • Three Star hotel
  • 100 rooms in hotel
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Excellent 9.2 /10 Reviews Call BookMore Details
Sleep Inn & Suites Winchester near University 140 Costello Dr, Winchester, VA 22602 +1-888-841-5292 ~18.41 miles northwest of Upperville
  • Has swimming pool: Pool hoist on site, Wheelchair-accessible pool.
  • 3 star hotel
  • Free breakfast available
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Average 7.6 /10 Reviews Call BookMore Details
Holiday Inn Winchester Se-Historic Gateway by IHG 333 Front Royal Pike, Winchester, VA 22602 +1-888-455-5160 ~18.45 miles northwest of Upperville
  • Has swimming pool: Wheelchair-accessible pool.
  • 3-star hotel
  • Check-in time: 3:00 PM - 7:00 AM
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Very Good 8.9 /10 Read Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Winchester 250 Front Royal Pike, Winchester, VA 22601 +1-888-965-8297 ~18.54 miles northwest of Upperville
  • Pool details: Wheelchair-accessible pool.
  • 3-star hotel
  • Access to gym on-site
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Excellent 9.2 /10 Hotel Reviews Call BookMore Details
Holiday Inn Express Winchester South-Stephens City by IHG 165 Town Run Ln, Stephens City, VA 22655 +1-888-906-6358 ~18.56 miles west of Upperville
  • 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.
  • Three Star hotel
  • 71 sleeping rooms in hotel
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Very Good 8.2 /10 Review Score Call BookMore Details
Quality Inn Stephens City - Winchester South 167 Town Run Ln, Stephens City, VA 22655 +1-888-749-6785 ~18.57 miles west of Upperville
  • Includes a pool
  • Mid-scale property
  • 2 floors in property
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Very Good 8.0 /10 Hotel Reviews Call BookMore Details
Country Inn & Suites by Radisson Winchester, VA 141 Kernstown Commons Blvd, Winchester, VA 22602 +1-888-878-9982 ~18.67 miles west of Upperville
  • We have a pool ready for use
  • Midscale property
  • Fitness + Health Center
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Very Good 8.4 /10 Recent Reviews Call BookMore Details
Home2 Suites by Hilton Winchester 240 Crossover Blvd, Winchester, VA 22601 +1-888-389-4485 ~18.70 miles northwest of Upperville
  • We have a pool
  • Affordable property
  • Check in: 15:00:00
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Excellent 9.4 /10 Guest Reviews Call BookMore Details
Clarion Inn & Conference Center 711 Millwood Avenue, Winchester, VA 22601 +1-888-389-4121 ~18.78 miles northwest of Upperville
  • Includes a pool
  • Low-priced property
  • 139 rooms in property
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TownePlace Suites by Marriott Winchester 170 Getty Ln, Winchester, VA 22603 +1-888-675-2083 ~18.79 miles northwest of Upperville
  • Includes a pool: Swimming pool, Wheelchair-accessible pool. Pool access available from 6 AM to 10 PM.
  • 3-star property
  • Access to gym on-site
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Very Good 8.8 /10 Read Reviews Call BookMore Details
Hampton Inn Warrenton 501 Blackwell Rd, Warrenton, VA 20186 +1-800-716-8490 ~18.93 miles south of Upperville
  • Includes a pool: Wheelchair-accessible pool.
  • Mid-scale hotel
  • Fitness center on property
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Excellent 9.0 /10 Read Reviews Call BookMore Details
APM Inn & Suites 1347 Berryville Ave, Winchester, VA 22601 +1-800-805-5223 ~18.93 miles northwest of Upperville
  • Pool in hotel
  • Two star property
  • Check in time: 3:00 PM - 10:00 PM
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Average 7.0 /10 Guest Reviews Call BookMore Details
Baymont by Wyndham Warrenton 7379 Comfort Inn Drive, Warrenton, VA 20187 +1-888-965-1860 ~18.94 miles south of Upperville
  • Includes a pool: Wheelchair-accessible pool, Outdoor seasonal pool. The seasonal pool will be open from May 31 to September 01.
  • Affordable Motel property
  • Pets are OK
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Average 6.2 /10 Hotel Reviews Call BookMore Details
Hampton Inn Winchester-University / Mall Area 640 East Jubal Early Drive, Winchester, VA 22601 +1-888-788-5576 ~18.98 miles northwest of Upperville
  • Has swimming pool: 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 hotel
  • Pets Welcome
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Excellent 9.0 /10 Read Reviews Call BookMore Details
Hampton Inn Winchester N / Conference Center VA 1204 Berryville Avenue, Winchester, VA 22601 +1-888-897-9207 ~19.02 miles northwest of Upperville
  • Pool in hotel: Pool hoist on site, Wheelchair-accessible pool, Outdoor seasonal pool. The seasonal pool will be open from May to August.
  • Mid-scale property
  • Check-in: 3:00 PM
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Excellent 9.2 /10 Hotel Reviews Call BookMore Details
Spark by Hilton Winchester 150 Wingate Dr, Winchester, VA 22601 +1-888-311-4278 ~19.15 miles northwest of Upperville
  • Our hotel comes with a pool
  • 3-star property
  • 4 floors in property
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Excellent 9.2 /10 Read Reviews Call BookMore Details
Hilton Garden Inn Winchester 120 Wingate Drive, Winchester, VA 22601 +1-888-469-4795 ~19.24 miles northwest of Upperville
  • Pool in hotel: Swimming pool, Pool hoist on site, Wheelchair-accessible pool. Pool access available from 10:00 AM to 10 PM.
  • Mid-scale property
  • Fitness + Health Center
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Excellent 9.0 /10 Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites Warrenton by IHG 410 Holiday Court, Warrenton, VA 20186 +1-888-734-9421 ~19.41 miles south of Upperville
  • Pool details: Outdoor seasonal pool. The seasonal pool will be open from May to September. Pool access available from 8:00 AM to 10 PM.
  • Mid-scale property
  • Gym is available on property
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Very Good 8.8 /10 Latest Reviews Call BookMore Details
The George Washington Hotel a Wyndham Grand Hotel 103 East Piccadilly St, Winchester, VA 22601 +1-888-841-5292 ~19.91 miles northwest of Upperville
  • Our hotel comes with a pool
  • 3-star hotel
  • 90 rooms in hotel
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Excellent 9.1 /10 Recent Reviews Call BookMore Details
Holiday Inn Express & Suites Leesburg - Historic District by IHG 80 Prosperity Ave. Se, Leesburg, VA 20175 +1-888-455-5160 ~19.98 miles east of Upperville
  • Pool details: Pool hoist on site, Wheelchair-accessible pool. Pool access available from 9:00 AM to 10:00 PM.
  • Three Star property
  • Check in time: 3:00 PM - midnight
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Excellent 9.0 /10 Guest Reviews Call BookMore Details
Best Western Leesburg Hotel & Conference Center 726 East Market St, Leesburg, VA 20176 +1-888-965-8297 ~20.16 miles east of Upperville
  • Has swimming pool: Outdoor seasonal pool. The seasonal pool will be open from May to September.
  • Affordable hotel
  • Pets are OK
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Very Good 8.0 /10 Read Reviews Call BookMore Details
Hampton Inn by Hilton Gainesville-Haymarket 7300 Atlas Walk Way, Gainesville, VA 20155 +1-888-906-6358 ~20.29 miles southeast of Upperville
  • Includes a pool: Pool hoist on site, Wheelchair-accessible pool. Pool access available from 8:00 AM to 10:00 PM.
  • 3-star hotel
  • Pet-friendly
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Excellent 9.0 /10 Guest Reviews Call BookMore Details
Hampton Inn & Suites Leesburg 117 Fort Evans Rd, Leesburg, VA 20176 +1-888-749-6785 ~20.31 miles east of Upperville
  • Includes a pool: Wheelchair-accessible pool. Pool access available from 6:00 AM to 10:00 PM.
  • 3-star hotel
  • Complimentary breakfast is offered
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Very Good 8.6 /10 Guest Reviews Call BookMore Details
Homewood Suites by Hilton Leesburg 115 Fort Evans Rd. Ne, Leesburg, VA 20176 +1-888-878-9982 ~20.33 miles east of Upperville
  • Pool details: Wheelchair-accessible pool, Pool sun loungers. Pool access available from 8 AM to 10 PM.
  • 3-star hotel
  • Pets are Welcome
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Excellent 9.0 /10 Hotel Reviews Call BookMore Details
Microtel Inn & Suites by Wyndham Winchester 150 Faraday Plaza, Winchester, VA 22603 +1-888-389-4485 ~20.47 miles northwest of Upperville
  • Pool in hotel: Pool hoist on site, Wheelchair-accessible pool. Pool access available from 7:00 AM to 11:00 PM.
  • 3-star property
  • Check-in time: 3:00 PM
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Very Good 8.7 /10 Reviews Call BookMore Details
Econo Lodge Inn & Suites Middletown - Winchester South 91 Reliance Road, Middletown, VA 22645 +1-888-389-4121 ~20.59 miles west of Upperville
  • Includes a swimming pool
  • Economy hotel
  • 48 sleeping rooms in hotel
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Poor 5.8 /10 Latest Reviews Call BookMore Details
Quality Inn Winchester 1601 Martinsburg Pike, Winchester, VA 22603 +1-888-675-2083 ~20.63 miles northwest of Upperville
  • Pool available: Outdoor seasonal pool. The seasonal pool will be open from May to September.
  • 3 star property
  • 2 floors in hotel
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Excellent 9.4 /10 Guest Reviews Call BookMore Details
SpringHill Suites by Marriott Winchester 280 MARKET STREET, Winchester, VA 22603 +1-800-716-8490 ~20.67 miles northwest of Upperville
  • Has swimming pool: Wheelchair-accessible pool.
  • Mid-scale property
  • 96 suites in property
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Excellent 9.4 /10 Recent Reviews Call BookMore Details
TRU by Hilton Winchester 118 Mercedes Court, Winchester, VA 22603 +1-800-805-5223 ~20.72 miles northwest of Upperville
  • Has swimming pool: Wheelchair-accessible pool.
  • 3 star property
  • 90 rooms in hotel
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Excellent 9.2 /10 Reviews Call BookMore Details
SpringHill Suites by Marriott Gainesville Haymarket 7921 Gateway Promenade Place, Gainesville, VA 20155 +1-888-965-1860 ~20.77 miles southeast of Upperville
  • Includes a pool: Wheelchair-accessible pool.
  • Affordable property
  • Hotel has 110 rooms
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Excellent 9.4 /10 Read Reviews Call BookMore Details
Home2 Suites by Hilton Leesburg 420 Fort Evans Rd. NE, Leesburg, VA 20176 +1-888-788-5576 ~20.90 miles east of Upperville
  • Has swimming pool: Pool hoist on site, Wheelchair-accessible pool.
  • Mid-scale property
  • Pets Welcome
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Excellent 9.2 /10 Review Score Call BookMore Details
HomeTowne Studios by Red Roof Leesburg 1500 East Market St. Building B, Leesburg, VA 20176 +1-888-897-9207 ~20.90 miles east of Upperville
  • Pool available: Pool hoist on site, Wheelchair-accessible pool.
  • 3-star property
  • Check-in time: 3:00 PM - anytime
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Poor 4.9 /10 Recent Reviews Call BookMore Details
Carradoc Hall Hotel & Conference Center - Leesburg by The Red Collection 1500 East Market St, Leesburg, VA 20176 +1-888-311-4278 ~20.93 miles east of Upperville
  • Includes a pool: Wheelchair-accessible pool.
  • 3 star hotel
  • Access to gym on-site
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Average 6.6 /10 Guest Reviews Call BookMore Details
Home2 Suites by Hilton Chantilly Dulles Airport 43340 Defender Dr, Chantilly, VA 20152 +1-888-469-4795 ~21.30 miles east of Upperville
  • Includes a pool: Wheelchair-accessible pool, Pool sun loungers.
  • Three Star hotel
  • Check-in: 3:00 PM - 11:00 AM
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Very Good 8.8 /10 Reviews Call BookMore Details
Hampton Inn & Suites Charles Town 157 Pimlico Dr, Charles Town, WV 25414 +1-888-734-9421 ~21.49 miles north of Upperville
  • Has swimming pool: Wheelchair-accessible pool. Pool access available from 8 AM to 11 PM.
  • Mid-scale hotel
  • Free comp. breakfast
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Excellent 9.4 /10 Latest Reviews Call BookMore Details
Home2 Suites by Hilton Charles Town 70 Jefferson Crossing Way, Charles Town, WV 25414 +1-888-841-5292 ~21.50 miles north of Upperville
  • Pool details: Swimming pool, Wheelchair-accessible pool. Pool access available from 8:00 AM to 11:00 PM.
  • Affordable hotel
  • Fitness center on property
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Courtyard by Marriott Winchester 300 Marriott Drive, Winchester, VA 22603 +1-888-455-5160 ~21.71 miles northwest of Upperville
  • Pool available: Swimming pool, Wheelchair-accessible pool. Pool access available from 7:00 AM to 11 PM.
  • Three Star hotel
  • Hotel has 136 rooms
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Excellent 9.0 /10 Hotel Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites Winchester by IHG 142 Foxridge Ln, Winchester, VA 22603 +1-888-965-8297 ~21.72 miles northwest of Upperville
  • Pool in hotel: Pool access available from 9:00 AM to 10:00 PM.
  • Midscale hotel
  • 25 suites in hotel
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Excellent 9.0 /10 Read Reviews Call BookMore Details
Holiday Inn Express Charles Town by IHG 681 Flowing Springs Rd, Charles Town, WV 25438 +1-888-906-6358 ~21.77 miles north of Upperville
  • Pool details: Pool hoist on site, Wheelchair-accessible pool. Pool access available from 7 AM to 11 PM.
  • Three Star hotel
  • 145 sleeping rooms in hotel
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Excellent 9.2 /10 Hotel Reviews Call BookMore Details
Aloft by Marriott Dulles Airport North 22390 Flagstaff Plz, Ashburn, VA 20148 +1-888-749-6785 ~21.95 miles east of Upperville
  • Pool available: Pool hoist on site, Wheelchair-accessible pool, Access to nearby indoor pool, Swimming pool. Pool access available from 7:00 AM to 10:00 PM.
  • 3-star property
  • Pets are Allowed
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Very Good 8.4 /10 Recent Reviews Call BookMore Details
Hilton Garden Inn Dulles North 22400 Flagstaff Plaza, Ashburn, VA 20148 +1-888-878-9982 ~22.00 miles east of Upperville
  • Includes a pool: Wheelchair-accessible pool.
  • Affordable property
  • 135 sleeping rooms in hotel
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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863 a service by Reservations.ai
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Very Good 8.4 /10 Reviews Call BookMore Details
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