Find hotels with pools in Old Town Winchester, Winchester from $78

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Check availability on Old Town Winchester Hotels with a Pool

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Nov 30 - Dec 1
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Dec 1 - Dec 2
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Dec 5 - Dec 7
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Dec 12 - Dec 14

Top Old Town Winchester Hotels with a Pool

Indoor pool
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
Old Town Winchester
  • Indoor pool
  • Full-service spa
9.4 out of 10, Exceptional, (1007)
Swimming enthusiasts revel in the refreshing indoor pool, a serene oasis within this Georgian-style landmark. After invigorating laps, guests explore nearby hiking trails or pamper themselves with professional massage treatments at the on-site spa.
$127 nightly
The price is $144
Dec 1 - Dec 2
Total with taxes and fees
The George Washington Hotel, A Wyndham Grand Hotel
Indoor pool
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3.0 star property
Winchester
  • Indoor pool
9.2 out of 10, Wonderful, (2240)
Modern swimmers appreciate the immaculately maintained indoor pool, perfect for year-round enjoyment regardless of weather. The hotel complements aquatic recreation with a well-equipped fitness center, peaceful atmosphere, and complimentary breakfast buffet.
$95 nightly
The price is $104
Dec 14 - Dec 15
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester
Indoor pool
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 star property
Winchester
  • Indoor pool
9.2 out of 10, Wonderful, (1372)
Sparkling clean water welcomes swimmers to the indoor pool, accessible from 7:00 AM until 11:00 PM. Located near the Shenandoah Valley Museum, this peaceful hotel offers immaculate rooms and a fitness center for complete relaxation.
$72 nightly
The price is $78
Dec 15 - Dec 16
Total with taxes and fees
Microtel Inn & Suites by Wyndham Winchester
Indoor pool
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 star property
Winchester
  • Indoor pool
9.4 out of 10, Exceptional, (770)
Crystal-clear waters await in the immaculately maintained indoor pool, perfect for families seeking aquatic fun regardless of weather. Guests appreciate the convenient location near Winchester Medical Center, comfortable rooms with pillowtop mattresses, and exceptional breakfast variety.
$101 nightly
The price is $110
Dec 7 - Dec 8
Total with taxes and fees
SpringHill Suites by Marriott Winchester
Indoor pool
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3.0 star property
Winchester
  • Indoor pool
9.0 out of 10, Wonderful, (1004)
Sparkling waters await in the pristine indoor pool, a refreshing retreat after exploring nearby Shenandoah University attractions. Complemented by a 24-hour fitness center, Kems Restaurant, and spotlessly clean accommodations praised by travelers.
$78 nightly
The price is $85
Dec 8 - Dec 9
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG
Indoor pool
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 star property
Winchester
  • Indoor pool
9.0 out of 10, Wonderful, (758)
Swimming enthusiasts savor the year-round indoor pool complementing a comprehensive health club experience. Clean, comfortable rooms and attentive service await after aquatic adventures, while free continental breakfast energizes guests for another day of splashing fun.
$79 nightly
The price is $86
Dec 10 - Dec 11
Total with taxes and fees
TRU By Hilton Winchester
Seasonal outdoor pool
Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

2.5 star property
Winchester
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
9.2 out of 10, Wonderful, (842)
Poolside serenity awaits at the seasonal summer oasis, perfectly complementing days spent exploring nearby hiking trails or kayaking spots. Impeccably clean facilities, praised by guests, enhance this refreshing retreat after outdoor adventures.
$103 nightly
The price is $117
Dec 7 - Dec 8
Total with taxes and fees
Hampton Inn Winchester N/Conference Center, VA
Indoor pool
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

2.5 star property
Winchester
  • Indoor pool
9.0 out of 10, Wonderful, (796)
Splashing in the pristine indoor pool offers a welcome respite after exploring local trails. Beyond water delights, this Art Deco hotel features continental breakfast, a fitness center, and spacious rooms with plush, comfortable beds for perfect rest.
$93 nightly
The price is $101
Dec 3 - Dec 4
Total with taxes and fees
Fairfield Inn & Suites by Marriott Winchester
Indoor pool
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

4.0 star property
Front Royal
  • Indoor pool
  • Hot tub
9.0 out of 10, Wonderful, (1006)
Sparkling waters await in the pristine indoor pool where relaxation flows naturally into the adjacent hot tub. Beyond aquatic pleasures, this hotel offers an 18-hole golf course, 24-hour fitness center, and on-site dining at Houlihans Restaurant.
$123 nightly
The price is $135
Dec 14 - Dec 15
Total with taxes and fees
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Seasonal outdoor pool, open 9 AM to 10 PM, sun loungers
Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

2.5 star property
Stephens City
  • Pool loungers
8.2 out of 10, Very Good, (799)
Seasonal outdoor pool beckons from 9 AM to 10 PM between June and September, complete with comfortable sun loungers for lazy afternoon relaxation. This quiet, rural hotel complements poolside enjoyment with a hearty free breakfast buffet each morning.
$83 nightly
The price is $91
Dec 3 - Dec 4
Total with taxes and fees
Holiday Inn Express Winchester South-Stephens City by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Old Town Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"It was great"
Lisa 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Winchester

Frequently asked questions

What are some hotels with pools in Old Town Winchester?
The George Washington Hotel, A Wyndham Grand Hotel: Features 2 restaurants, an indoor pool, and a full-service spa. Travelodge by Wyndham Winchester: Provides buffet, an indoor pool, and complimentary wired internet access. La Quinta Inn & Suites by Wyndham Winchester: Offers daily, an indoor pool, and free self parking. Comfort Inn & Suites Winchester: Features buffet, an indoor pool, and complimentary wired internet access. Microtel Inn & Suites by Wyndham Winchester: Offers buffet, a seasonal outdoor pool, and complimentary wired internet access.
What is there to see and do in Old Town Winchester?
Make a point to visit attractions like Shenandoah Valley Discovery Museum. Discover sights such as Bright Box Theater, Old Court House Civil War Museum, and Handley Regional Library during your stay. Old Town Winchester appeals to visitors with its array of dining options and interesting historical sites.
When is the best time to book a hotel with a pool in Old Town Winchester?
You may want to think about a place to stay that has an outdoor pool if you're planning to visit in the warmest months of July, August, or June when the average temperature is 72°F. Lodging offering an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temperature is 36°F.

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