trover photo by Fernando Begay

Winchester, VA Hotels with an Outdoor Pool $49

Search over 1 million properties and 550 airlines worldwide

No Expedia cancellation fee to change or cancel almost any hotel reservation

Search over 1 million flights, hotels, packages, and more

Top Winchester Hotels with an Outdoor Pool

Country Inn & Suites by Radisson, Winchester, VA
3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
Free CancellationReserve now, pay when you stay
$89
per night
Feb 2 - Feb 3
4.5/5Wonderful! (1,744 reviews)

"Excellent property - only negative is noise from the on ramp to the I 95. Ask for a room at the front of the hotel."…"

Reviewed on Jan 22, 2020

Country Inn & Suites by Radisson, Winchester, VA
Twi-Lite Motel
2 out of 5
53 West 14th Street, Front Royal, VA
Free CancellationReserve now, pay when you stay
$55
per night
Jan 27 - Jan 28
3.9/5Very Good! (225 reviews)

"Nice clean, quiet motel for a very reasonable price."…"

Reviewed on Nov 21, 2019

Twi-Lite Motel
The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5
103 E Piccadilly St, Winchester, VA
Free CancellationReserve now, pay when you stay
$93
per night
Feb 2 - Feb 3
4.7/5Exceptional! (1,130 reviews)

"Beautiful old hotel with history galore! Loved our stay! Walking distance to the walking mall was wonderful!"…"

Reviewed on Jan 21, 2020

The George Washington Hotel, A Wyndham Grand Hotel
Travelodge by Wyndham Winchester
2 out of 5
160 Front Royal Pike, Winchester, VA
Free CancellationReserve now, pay when you stay
$49
per night
Feb 2 - Feb 3
3.5/5Good! (1,668 reviews)

"It was fine for the money we paid, and while it was not the RITZ, it was all we required."…"

Reviewed on Jan 12, 2020

Travelodge by Wyndham Winchester
Wingate by Wyndham Winchester
2.5 out of 5
150 Wingate Dr, Winchester, VA
Free CancellationReserve now, pay when you stay
$80
per night
Feb 2 - Feb 3
4.4/5Excellent! (1,145 reviews)

"We loved the spa bath in our King sized room. We'd come back just for that!"…"

Reviewed on Jan 23, 2020

Wingate by Wyndham Winchester
Quality Inn
2.5 out of 5
1601 Martinsburg Pike, Winchester, VA
Free CancellationReserve now, pay when you stay
$76
per night
Jan 28 - Jan 29
4.2/5Excellent! (506 reviews)

"Better than most $100 per night and up hotels that i have stayed in. Can't beat it for the money!"…"

Reviewed on Jan 13, 2020

Quality Inn
Baymont by Wyndham Front Royal Near Shenandoah National Park
2.5 out of 5
10 S Commerce Ave, Front Royal, VA
Free CancellationReserve now, pay when you stay
$59
per night
Feb 1 - Feb 2
3.3/5 (402 reviews)

"Perfect location to start Skyline Drive.. The Thai restaurant adjacent in the same building was awesome."…"

Reviewed on Oct 18, 2018

Baymont by Wyndham Front Royal Near Shenandoah National Park
Hampton Inn Winchester-University/Mall Area
2.5 out of 5
640 East Jubal Early Drive, Winchester, VA
Free CancellationReserve now, pay when you stay
$93
per night
Feb 1 - Feb 2
4.5/5Wonderful! (778 reviews)

"Perfect location, right off 81. Good breakfast! Staff was a little loud early in the morning (we were on the 4th floor), and it was Sunday morning."…"

Reviewed on Dec 3, 2019

Hampton Inn Winchester-University/Mall Area
Holiday Inn Express Winchester South-Stephens City
2.5 out of 5
165 Town Run Ln, Stephens City, VA
Free Cancellation
$75
per night
Feb 6 - Feb 7
4.1/5Very Good! (346 reviews)

"A great place to stay,already booked a room on our trip back north."…"

Reviewed on Jan 13, 2020

Holiday Inn Express Winchester South-Stephens City
La Quinta Inn & Suites by Wyndham Winchester
3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Free CancellationReserve now, pay when you stay
$89
per night
Feb 2 - Feb 3
4.3/5Excellent! (1,668 reviews)

"Staff was great, very pet friendly, great location right off 81 and several restaurants and gas stations, nice little shop for soda or snacks in lobby. Decor is nice, very up to date."…"

Reviewed on Jan 10, 2020

La Quinta Inn & Suites by Wyndham Winchester
Clarion Inn & Conference Center
2.5 out of 5
711 Millwood Ave, Winchester, VA
Free CancellationReserve now, pay when you stay
$51
per night
Feb 8 - Feb 9
3.8/5Good! (877 reviews)

"Smoking rooms clean nice people at the front desk."…"

Reviewed on Jan 20, 2020

Clarion Inn & Conference Center
Holiday Inn & Suites Front Royal Blue Ridge Shadows
3 out of 5
111 Hospitality Drive, Front Royal, VA
Free Cancellation
$99
per night
Jan 28 - Jan 29
4.5/5Wonderful! (605 reviews)

"Closeness to Virginia wineries. Wish there had been breakfast."…"

Reviewed on Nov 26, 2019

Holiday Inn & Suites Front Royal Blue Ridge Shadows
 Quality Inn Stephens City-Winchester South
2.5 out of 5
167 Town Run Ln, Stephens City, VA
Free CancellationReserve now, pay when you stay
$68
per night
Feb 8 - Feb 9
3.9/5Very Good! (292 reviews)

"Great staff and the property is conveniently located just off I-81. Go eat at Paladin, great restaurant about 1/2 mile down the street."…"

Reviewed on Jan 6, 2020

 Quality Inn Stephens City-Winchester South
Hampton Inn Winchester N/Conference Center, VA
2.5 out of 5
1204 Berryville Avenue, Winchester, VA
Free CancellationReserve now, pay when you stay
$89
per night
Feb 1 - Feb 2
4.4/5Excellent! (322 reviews)

"The staff was remarkable. So frriendly and helpful. They seemed to genuinely love their job. They seemed to go the extra milewithout being asked to. The guest was super important"…"

Reviewed on Nov 8, 2019

Hampton Inn Winchester N/Conference Center, VA
L'Auberge Provencale
4 out of 5
13630 Lord Fairfax Hwy, White Post, VA
Free CancellationReserve now, pay when you stay
$149
per night
Jan 27 - Jan 28
4.6/5Wonderful! (48 reviews)

"Awesome romantic place! Very nice very clean staff are amazing. Food is amazing, perfect spot. Highly recommend!!"…"

Reviewed on Nov 24, 2019

L'Auberge Provencale
TownePlace Suites by Marriott Winchester
2.5 out of 5
170 Getty Ln, Winchester, VA
Free CancellationReserve now, pay when you stay
$98
per night
Jan 30 - Jan 31
4.3/5Excellent! (257 reviews)
a great place for a great price

"Great hotel, friendly staff. Clean and comfortable"…"

Reviewed on Aug 22, 2019

TownePlace Suites by Marriott Winchester
Hampton Inn Front Royal
2.5 out of 5
9800 Winchester Rd, Front Royal, VA
Free CancellationReserve now, pay when you stay
$94
per night
Feb 1 - Feb 2
4.3/5Excellent! (747 reviews)

"Convenient acres to highway, clean and quiet and staff was friendly"…"

Reviewed on Nov 12, 2019

Hampton Inn Front Royal
Sleep Inn & Suites
2.5 out of 5
140 Costello Dr, Winchester, VA
Free CancellationReserve now, pay when you stay
$63
per night
Feb 2 - Feb 3
4.2/5Very Good! (504 reviews)

"It was OK! would book again if I take another trip next year"…"

Reviewed on Dec 27, 2019

Sleep Inn & Suites
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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.

Pocket Guide: Hotels with an Outdoor Pool in Winchester

Search for hotels in Winchester on Expedia. You can easily find your hotels in Winchester using one of the methods below:

  • View our selection of featured hotels in Winchester
  • Use the map to find hotels in the Winchester neighborhood you prefer
  • Use the filters to see hotels in a specific area of Winchester, select a specific theme, brand, or hotel class from basic (1 Star) to luxury hotels (5 Stars) in Winchester
  • Enter your travel dates to view the best deals on hotels in Winchester - while they last

More trip options

Recently Booked Hotels with an Outdoor Pool in Winchester

Travelers Loved These Hotels with an Outdoor Pool