Hotels with Swimming Pools in Winchester

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Hotels with Swimming Pools

Tonight
28 Nov - 29 Nov
Tomorrow
29 Nov - 30 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Hotels with Swimming Pools in 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 centre for complete relaxation.
The price is S$105
includes taxes & fees
28 Dec - 29 Dec
Microtel Inn & Suites by Wyndham Winchester
Seasonal outdoor pool, open 9 AM to 10 PM, pool 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, (798)
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.
The price is S$117
includes taxes & fees
10 Dec - 11 Dec
Holiday Inn Express Winchester South-Stephens City by IHG
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, (795)
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 centre, and spacious rooms with plush, comfortable beds for perfect rest.
The price is S$131
includes taxes & fees
1 Dec - 2 Dec
Fairfield Inn & Suites by Marriott Winchester
Indoor pool
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 star property
Winchester
  • Indoor pool
9.0 out of 10, Wonderful, (757)
Swimming enthusiasts savour 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 energises guests for another day of splashing fun.
The price is S$113
includes taxes & fees
29 Dec - 30 Dec
TRU By Hilton Winchester
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, (2238)
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 centre, peaceful atmosphere, and complimentary breakfast buffet.
The price is S$132
includes taxes & fees
16 Dec - 17 Dec
La Quinta Inn & Suites by Wyndham 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, (1003)
Sparkling waters await in the pristine indoor pool, a refreshing retreat after exploring nearby Shenandoah University attractions. Complemented by a 24-hour fitness centre, Kems Restaurant, and spotlessly clean accommodation praised by travellers.
The price is S$110
includes taxes & fees
8 Dec - 9 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
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 Centre, comfortable rooms with pillowtop mattresses, and exceptional breakfast variety.
The price is S$143
includes taxes & fees
28 Dec - 29 Dec
SpringHill Suites by Marriott Winchester
Seasonal outdoor pool
Quality Inn Winchester

Quality Inn Winchester

2.5 star property
Winchester
  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
  • Free WiFi
  • Restaurant
9.2 out of 10, Wonderful, (1006)
Splash into the refreshing seasonal pool after exploring nearby attractions. Modern rooms with comfortable beds await after swimming, while the complimentary continental breakfast earns consistent praise from travellers for its variety and attentive service.
The price is S$107
includes taxes & fees
10 Dec - 11 Dec
Quality Inn Winchester
Indoor pool
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

3.0 star property
Winchester
  • Indoor pool
8.8 out of 10, Excellent, (1011)
Swimming awaits at the immaculate indoor pool, a peaceful retreat after exploring nearby Shenandoah University. Fitness enthusiasts appreciate the well-maintained workout centre, while pet owners enjoy designated pet-friendly rooms and spacious grounds for walking companions.
The price is S$129
includes taxes & fees
14 Dec - 15 Dec
Country Inn & Suites by Radisson, Winchester, VA
Indoor pool
Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 star property
Front Royal
  • Indoor pool
9.0 out of 10, Wonderful, (1008)
Sparkling pool waters await after exploring nearby national parks. Guests consistently praise the spotless facilities, comfortable rooms with modern furnishings, and exceptionally friendly staff who go above and beyond at this peaceful mountain retreat.
The price is S$143
includes taxes & fees
28 Dec - 29 Dec
Hampton Inn Front Royal
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.
View all properties

Black Friday Sale

Save up to 50% on select hotels
Book now

Top Winchester Hotel Reviews

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"Great stay!"
gary 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Winchester, VA

Explore a world of travel with Expedia

Frequently asked questions

What's it like visiting Winchester?
If lounging by a pool is your idea of the perfect getaway, you may want to consider historic Winchester, which offers 6 places to stay with pools. While you're here, you can explore sights such as Bright Box Theater and Shenandoah Valley Discovery Museum, and then unwind poolside at one of the accommodation options in Winchester that guests like for their pools.
What are some hotels with pools in Winchester?
La Quinta Inn & Suites by Wyndham Winchester: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. Microtel Inn & Suites by Wyndham Winchester: Offers daily, an indoor pool and free self parking. Hilton Garden Inn Winchester: Provides a snack bar/deli, a pool and complimentary high-speed (wired) Internet access. Courtyard by Marriott Winchester: Features a snack bar/deli, a pool and complimentary high-speed (wired) Internet access. TownePlace Suites by Marriott Winchester: Offers a snack bar/deli, a pool and daily.
How many hotels with pools should I expect to find in Winchester?
Expedia has 6 hotels in Winchester for your poolside break.
What is there to see and do in Winchester?
Make a point to visit attractions such as Shenandoah Valley Discovery Museum and Rocking S Ranch. During your stay, visit sights such as Bright Box Theater, Patsy Cline Historic House and Museum of the Shenandoah Valley. Winchester appeals to visitors with its array of dining options, interesting historical sites and major shopping area.
When is the best time to book a hotel with a pool in Winchester?
You may want to think about accommodation that has an outdoor pool if you'll be visiting Winchester in the warmest months of July, August or June, when the average temperature is 22°C. Accommodation offering an indoor pool may be what you want if you come to town during the coldest months of January, February or December, when the average temp is 2°C.