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 Rd.
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
36205 Snake Hill Rd., Middleburg, VA 20117 +1-888-389-4121 ~7.37 miles east of Upperville
  • Has swimming pool: Outdoor heated pool. Open seasonally May - September. Pool may be closed due to private events.
  • 3-star Rural hotel
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From$350
Average 3.0 /5 Guest Reviews Call BookMore Details
Sleep Inn & Suites Winchester near University : 140 Costello Dr.
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
140 Costello Dr., Winchester, VA 22602 +1-888-675-2083 ~18.35 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.
  • Cheap Suburban property
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From$60
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Quality Inn Stephens City - Winchester South : 167 Town Run Lane
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
167 Town Run Lane, Stephens City, VA 22655 +1-800-716-8490 ~18.47 miles west of Upperville
  • Includes a pool: The outdoor seasonal pool is open from 9:00am to 9:00pm
  • Three Star Highway property
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From$60
Very Good 4.0 /5 Read Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
250 Front Royal Pike, Winchester, VA 22602 +1-800-805-5223 ~18.50 miles northwest of Upperville
  • Has swimming pool: Indoor Pool 6am - 10pm
  • 3-star Suburban property
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From$85
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express in Stephens City
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
165 Town Run Ln, Stephens City, VA 22655 +1-888-965-1860 ~18.52 miles west of Upperville
  • Has swimming pool
  • Affordable Rural hotel
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From$68
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Travelodge by Wyndham Winchester
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
160 Front Royal Pike, Winchester, VA 22602 +1-888-788-5576 ~18.52 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 property
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From$49
Average 3.0 /5 Reviews Call BookMore Details
Country Inn & Suites
+1-888-897-9207

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141 Kernstown Commons Blvd., Winchester, VA 22602 +1-888-897-9207 ~18.61 miles west of Upperville
  • Has swimming pool: Indoor heated pool & hot tub open daily from 6am-12am (midnight)
  • 3-star Suburban hotel
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Towneplace Suites by Marriott Winchester
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
170 Getty Ln, Winchester, VA 22603 +1-888-311-4278 ~18.75 miles northwest of Upperville
  • We have a pool ready for use
  • Mid-scale Suburban property
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From$74
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Hampton Inn Winchester University / Mall Area - Winchester
+1-888-469-4795

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640 East Jubal Early Dr., Winchester, VA 22601 +1-888-469-4795 ~18.94 miles northwest of Upperville
  • Pool available: Seasonal Outdoor Pool that is open from 8 am to 10 pm
  • Three Star Highway hotel
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From$82
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Baymont Inn & Suites Warrenton - Warrenton
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
7379 Comfort Inn Dr., Warrenton, VA 20187 +1-888-734-9421 ~19.03 miles south of Upperville
  • Has swimming 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.
  • Inexpensive Suburban property
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From$60
Average 3.0 /5 Read Reviews Call BookMore Details
Motel 6 Winchester Va
+1-888-841-5292

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2951 Valley Ave., Winchester, VA 22601 +1-888-841-5292 ~19.36 miles northwest of Upperville
  • With a pool!
  • Low-priced Suburban property
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From$60
Average 3.0 /5 Hotel Reviews Call BookMore Details
Microtel Inn & Suites by Wyndham Winchester - Winchester
+1-888-455-5160

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150 Faraday Plaza, Winchester, VA 22603 +1-888-455-5160 ~19.89 miles northwest of Upperville
  • Pool available: Indoor Pool - 10a-10pm
  • Low-priced Highway hotel
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From$60
Average 3.0 /5 Review Score Call BookMore Details
The George Washington a Wyndham Grand Hotel - Winchester
+1-888-965-8297

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103 East Piccadilly St., Winchester, VA 22601 +1-888-965-8297 ~19.90 miles northwest of Upperville
  • With a pool!
  • Mid-scale Downtown property
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From$99
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Leesburg
+1-888-906-6358

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117 Fort Evans Rd. Ne, Leesburg, VA 20176 +1-888-906-6358 ~20.23 miles east of Upperville
  • Pool available: Indoor Heated Pool 524 square feet 3-5ft Deep Open 6am-10pm
  • Affordable Suburban hotel
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From$80
Average 3.0 /5 Reviews Call BookMore Details
Homewood Suites by Hilton Leesburg Va in Leesburg
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
115 Fort Evans Rd. Ne, Leesburg, VA 20176 +1-888-749-6785 ~20.24 miles east of Upperville
  • Pool available: Outdoor Pool Open from 8:00 AM to 10:00 PM Pool open every year from Memorial Day to Labor Day
  • Three Star Downtown hotel
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From$119
Very Good 4.0 /5 Reviews Call BookMore Details
Quality Inn Winchester - Winchester
+1-888-878-9982

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1601 Martinsburg Pike, Winchester, VA 22603 +1-888-878-9982 ~20.58 miles northwest of Upperville
  • Pool in hotel: Our Seasonal Outdoor Pool hours are 9AM-10PM.
  • Two-star Highway property
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From$77
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Clarion Hotel & Conference Center Leesburg : 1500 East Market St.
+1-888-389-4485

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1500 East Market St., Leesburg, VA 20176 +1-888-389-4485 ~20.87 miles east of Upperville
  • Pool available: Very Large outdoor pool with Furniture to go all around
  • Mid-scale Suburban property
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From$75
Poor 2.0 /5 Reviews Call BookMore Details
Home 2 Chantilly - Chantilly
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
43340 Defender Dr., Chantilly, VA 20152 +1-888-389-4121 ~21.27 miles east of Upperville
  • Includes a pool: • INDOOR SWIMMING POOL is available 6 AM to 10 PM
  • Expensive Airport property
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From$109
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express & Suites
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
142 Fox Ridge Lane, Winchester, VA 22603 +1-888-675-2083 ~21.49 miles northwest of Upperville
  • Pool in hotel: 9am-10pm Indoor with Jacuzzi
  • Affordable Rural property
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From$75
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Courtyard by Marriott Winchester Medical Center in Winchester
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
300 Marriott Dr., Winchester, VA 22603 +1-800-716-8490 ~21.73 miles northwest of Upperville
  • Includes a pool: Indoor Pool and Whirlpool (Heated) Hours are 6:00 am - 11:00 pm
  • 3 star Suburban hotel
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From$89
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Charles Town by Ihg in Ranson
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
681 Flowing Springs Rd., Ranson, WV 25438 +1-800-805-5223 ~21.78 miles north of Upperville
  • Has swimming pool: Outdoor, seasonal
  • Affordable Mountain property
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From$80
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Aloft Dulles Airport North - Ashburn
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
22390 Flagstaff Plaza, Ashburn, VA 20148 +1-888-965-1860 ~21.87 miles east of Upperville
  • Pool available: Indoor pool
  • 3 star Airport property
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From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn Dulles North : 22400 Flagstaff Plaza
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
22400 Flagstaff Plaza, Ashburn, VA 20148 +1-888-788-5576 ~21.91 miles east of Upperville
  • Pool details: Indoor Pool
  • Three Star Suburban property
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From$64
Very Good 4.0 /5 Review Score Call BookMore Details
Embassy Suites by Hilton Dulles North Loudoun in Ashburn
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
44610 Waxpool Rd., Ashburn, VA 20147 +1-888-897-9207 ~23.02 miles east of Upperville
  • Pool available: Indoor/Outdoor Swimming pool
  • 3-star Airport property
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Homewood Suites by Hilton Dulles-North/Loudoun
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
44620 Waxpool Rd., Dulles, VA 20147 +1-888-311-4278 ~23.02 miles east of Upperville
  • Has swimming pool: Indoor/Outdoor Swimming pool
  • Midscale Airport property
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From$95
Average 3.0 /5 Guest Reviews Call BookMore Details
Clarion Inn Harpers Ferry Charles Town in Harpers Ferry
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
4328 William L Wilson Fwy, Harpers Ferry, WV 25425 +1-888-469-4795 ~23.45 miles north of Upperville
  • Includes a pool: 10am-10pm indoor
  • Midscale Mountain hotel
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From$72
Very Good 4.0 /5 Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Manassas Battlefield in Manassas
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
6950 Nova Way Manassas Va 20109, Manassas, VA 20109 +1-888-734-9421 ~23.63 miles southeast of Upperville
  • Pool available: 6am to 10pm Indoor
  • Affordable Suburban hotel
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Courtyard by Marriott Manassas Battlefield Park : 10701 Battleview Pkwy.
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
10701 Battleview Pkwy., Manassas, VA 20109 +1-888-841-5292 ~23.73 miles southeast of Upperville
  • Pool details: Indoor pool, open weekdays 5PM-10PM and weekends/holidays 10AM-10PM. Depth from 3 to 5 foot.
  • Affordable Suburban hotel
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From$70
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Washington Dulles Airport Marriott
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
45020 Aviation Dr., Dulles, VA 20166 +1-888-455-5160 ~23.78 miles east of Upperville
  • Has swimming pool: Indoor Pool: Everday from 6AM to 10PM Outdoor Pool: Seasonal
  • 3 star Airport property
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Manassas : 7001 Infantry Ridge Rd.
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
7001 Infantry Ridge Rd., Manassas, VA 20109 +1-888-965-8297 ~23.80 miles southeast of Upperville
  • Includes a pool: Indoor Pool
  • Mid-scale property
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From$90
Average 3.0 /5 Reviews Call BookMore Details
Wyndham Garden Manassas
+1-888-906-6358

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10800 Vandor Lane, Manassas, VA 20109 +1-888-906-6358 ~23.83 miles southeast of Upperville
  • Includes a pool: We offer Indoor Heated Pool and Out Door Pool (seasonal)
  • 3 star Suburban hotel
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From$53
Average 3.0 /5 Read Reviews Call BookMore Details
Best Western Battlefield Inn - Manassas
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
10820 Balls Ford Rd., Manassas, VA 20109 Website +1-888-749-6785 ~23.90 miles southeast of Upperville
  • Pool details: Large seasonal outdoor pool open 10am-10pm Patio area with lounging chairs
  • Cheap Suburban hotel
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From$45
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Springhill Suites by Marriott Ashburn Dulles North : 20065 Lakeview Center Plaza
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
20065 Lakeview Center Plaza, Ashburn, VA 20147 +1-888-878-9982 ~23.93 miles east of Upperville
  • Pool details: Indoor pool open from 10am-10pm
  • Affordable Suburban property
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From$79
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Washington-Dulles Int'l Airport South in Chantilly
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
4050 Westfax Dr., Chantilly, VA 20151 +1-888-389-4485 ~24.14 miles east of Upperville
  • Has swimming pool
  • Three Star Airport property
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Comfort Suites Manassas Battlefield Park
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
7350 Williamson Blvd., Manassas, VA 20109 +1-888-389-4121 ~24.23 miles southeast of Upperville
  • Includes a pool: Indoor pool with a Jacuzzi 15X25 Indoor
  • Three Star Highway property
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From$90
Average 3.0 /5 Guest Reviews Call BookMore Details
Ramada by Wyndham Strasburg - Strasburg
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
21 Signal Knob Dr., Strasburg, VA 22657 +1-888-675-2083 ~24.34 miles west of Upperville
  • Pool in hotel
  • Cheap Rural property
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From$63
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn & Suites Washington-Dulles International Airport
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
22700 Holiday Park Dr., Sterling, VA 20166 +1-800-716-8490 ~24.68 miles east of Upperville
  • Has swimming pool: We offer a large indoor swimming pool and hot tub. Both equipped with handicapped lifts for guests who would like it. The pool is open every day from 6am until 11pm. Key card required for entry
  • Three Star Airport property
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From$80
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn Washington Dulles in Dulles
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
1000 Sully Rd., Dulles, VA 20166 +1-800-805-5223 ~24.68 miles east of Upperville
  • Pool details: 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
  • Affordable Airport property
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From$79
Very Good 4.0 /5 Review Score Call BookMore Details
Holiday Inn Washington-Dulles International Airport by IHG
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
45425 Holiday Dr., Sterling, VA 20166 +1-888-965-1860 ~24.78 miles east of Upperville
  • Includes a pool: 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
  • Affordable Airport property
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From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Hyatt House Sterling Dulles Airport North
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
45520 Dulles Plaza, Sterling, VA 20166 +1-888-788-5576 ~24.87 miles east of Upperville
  • Pool available: Outdoor seasonal pool open from 10:00 AM - 09:00 PM. 20'x40'. 5' in deepest.
  • Midscale Airport property
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From$80
Average 3.0 /5 Read Reviews Call BookMore Details
The Westin Washington Dulles Airport in Herndon
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
2520 Wasser Terrace, Herndon, VA 20171 +1-888-897-9207 ~24.90 miles east of Upperville
  • Pool available: Permanently closed.
  • Mid-scale Airport property
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From$79
Average 3.0 /5 Reviews Call BookMore Details
Doubletree by Hilton Sterling Dulles Airport : 21611 Atlantic Blvd.
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
21611 Atlantic Blvd., Sterling, VA 20166 +1-888-311-4278 ~24.91 miles east of Upperville
  • Includes a pool: Heated indoor pool and whirlpool spa open from 5am to 10pm daily.
  • Mid-scale Airport property
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From$59
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Chantilly
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
4335 Chantilly Shopping Center, Chantilly, VA 20151 +1-888-469-4795 ~25.01 miles east of Upperville
  • Has swimming pool: an Outdoor Pool- opens on Memorial Day Weekend to Labor Day weekend from 10:00am - 8:00pm.
  • 3 star Airport property
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From$57
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hyatt Regency Dulles : 2300 Dulles Corner Blvd.
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
2300 Dulles Corner Blvd., Herndon, VA 20171 +1-888-734-9421 ~25.11 miles east of Upperville
  • Includes a pool: Open from Dawn to Dusk, come enjoy our indoor pool with heated whirlpool.
  • High-end Airport property
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From$75
Very Good 4.0 /5 Reviews Call BookMore Details
Hyatt Place Chantilly / Dulles Airport South
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
4994 Westone Plaza, Chantilly, VA 20151 +1-888-841-5292 ~25.18 miles east of Upperville
  • Includes a pool: Seasonal Outdoor Pool open from Memorial Day Weekend to Labor Day Weekend
  • Affordable Airport hotel
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From$99
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hyatt Place Herndon / Dulles Airport East - Herndon
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
13711 Sayward Blvd., Herndon, VA 20171 +1-888-455-5160 ~25.30 miles east of Upperville
  • Pool details: Swim away a long day of travel or hard work in our heated indoor mineral pool! Guests enjoy our Dulles airport hotel's wide pool and healthy depth range (4ft - 9ft) -- good for getting in some exercise or simply enjoying a dip with friends and family. Towels, pool chairs and chaises are provided. Hours: open daily from 6:00 a.m. - 10:00 p.m.
  • 3 star Airport property
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From$80
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Wingate by Wyndham Chantilly / Dulles Airport in Chantilly
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
3940 Centerview Dr., Chantilly, VA 20151 +1-888-965-8297 ~25.36 miles east of Upperville
  • Has swimming pool: Indoor Heated Pool/Jacuzzi 9 AM to 10 PM daily No Lifeguard on Duty
  • 3-star Airport hotel
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From$80
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Homewood Suites by Hilton Dulles Int'l Airport : 13460 Sunrise Valley Dr.
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
13460 Sunrise Valley Dr., Herndon, VA 20171 +1-888-906-6358 ~25.79 miles east of Upperville
  • Has swimming pool: Indoor Pool
  • Three Star Airport hotel
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From$75
Average 3.0 /5 Review Score Call BookMore Details
Hyatt Place Sterling Dulles Airport North
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
21481 Ridgetop Circle, Sterling, VA 20166 +1-888-749-6785 ~26.01 miles east of Upperville
  • Pool in hotel: Outdoor Pool
  • Midscale Airport hotel
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From$59
Very Good 4.0 /5 Review Score Call BookMore Details
Embassy Suites by Hilton Dulles Airport : 13341 Woodland Park Rd.
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
13341 Woodland Park Rd., Herndon, VA 20171 +1-888-878-9982 ~26.06 miles east of Upperville
  • Includes a pool: Come take a swim in our indoor pool with Jacuzzi. Open from 3pm - 10pm Monday through Thursday, and 9am - 10pm on Friday, Saturday, and Sunday.
  • Four star Airport property
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From$72
Very Good 4.0 /5 Recent Reviews Call BookMore Details
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