Hotels with a Pool in Winchester, VA
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Featured Winchester Hotels with Pool

Country Inn & Suites by Radisson, Winchester, VA
141 Kernstown Commons Blvd Winchester VA
Free Cancellation
$83 nightly
The price is $90 total per night
$90 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
At Country Inn & Suites by Radisson, Winchester, VA, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. Free parking is available if you drive. The front desk is staffed 24 hours a day to help with dry cleaning/laundry and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include conference space, a 24-hour business center, and a library.
Pool
Breakfast included

The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $143 total per night
$143 total
Dec 29 - Dec 30
Total with taxes and fees
At The George Washington Hotel, A Wyndham Grand Hotel, guests enjoy a full-service spa, an indoor pool, and a 24-hour gym. Valet parking is available for USD 15 per night. Front-desk staff can answer questions 24/7, and assist with securing valuables, luggage storage, and dry cleaning/laundry. Other amenities at this spa hotel include free WiFi in public areas, conference space, and a business center.
Pool
Spa

Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Free Cancellation
Reserve now, pay when you stay
$77 nightly
The price is $87 total per night
$87 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Spark by Hilton Winchester offers a gym, meeting rooms, and conference space. You can put free parking to good use if you drive. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a business center, express check-out, and laundry facilities.
Breakfast included
Pet friendly

La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $107 total per night
$107 total
Dec 25 - Dec 26
Total with taxes and fees
At La Quinta Inn & Suites by Wyndham Winchester, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. Free parking is included with your stay. The 24-hour front desk has staff standing by to help with dry cleaning/laundry and luggage storage. Additional amenities include meeting rooms, a business center, and express check-out.
Pool
Breakfast included

DoubleTree by Hilton Front Royal Blue Ridge Shadows
111 Hospitality Drive Front Royal VA
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $108 total per night
$108 total
Dec 29 - Dec 30
Total with taxes and fees
At DoubleTree by Hilton Front Royal Blue Ridge Shadows, guests enjoy a golf course, an indoor pool, and a 24-hour gym. Free parking is included with your stay. Multilingual staff at the 24-hour front desk can assist with luggage storage, concierge services, and dry cleaning/laundry. Other amenities at this golf hotel include free WiFi in public areas, a hot tub, and a conference center.
Pool
Hot Tub

Twi-Lite Inn
53 West 14th Street Front Royal VA
Free Cancellation
Reserve now, pay when you stay
$62 nightly
The price is $69 total per night
$69 total
Dec 24 - Dec 25
Total with taxes and fees
Twi-Lite Inn offers free WiFi in public areas and a seasonal outdoor pool. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready.
Pool
Parking included

Hampton Inn Front Royal
9800 Winchester Rd Front Royal VA
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $127 total per night
$127 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Guests staying at Hampton Inn Front Royal enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. You can take advantage of free parking if you drive. The front desk is staffed 24 hours a day to help with luggage storage and securing valuables. Additional amenities include conference space, coffee/tea in a common area, and express check-in.
Pool
Breakfast included

Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Free Cancellation
Reserve now, pay when you stay
$68 nightly
The price is $74 total per night
$74 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
Travelodge by Wyndham Winchester features free WiFi in public areas, coffee in a common area, and express check-out. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to assist with sightseeing, directions, and local dining recommendations. Additional amenities include laundry facilities, an ATM, and a TV in a common area.
Pet friendly
Parking included

Sleep Inn & Suites Winchester near University
140 Costello Dr Winchester VA
Free Cancellation
$62 nightly
The price is $67 total per night
$67 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
At Sleep Inn & Suites Winchester near University, guests have access to a gym, free WiFi in public areas, and meeting rooms. Free parking is included with your stay. The 24-hour front desk has staff standing by to help with dry cleaning/laundry and securing valuables. Additional amenities include a business center, coffee/tea in a common area, and free newspapers.
Breakfast included
Parking included

Hilton Garden Inn Winchester
120 Wingate Drive Winchester VA
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $114 total per night
$114 total
Dec 29 - Dec 30
Total with taxes and fees
Guests of Hilton Garden Inn Winchester have access to an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, dry cleaning/laundry, and luggage storage. Additional amenities include a conference center, a 24-hour business center, and coffee/tea in a common area.
Pool
Pet friendly

Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Free Cancellation
$85 nightly
The price is $92 total per night
$92 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
At Holiday Inn Winchester Se-Historic Gateway by IHG, guests enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, luggage storage, and securing valuables. Additional amenities include meeting rooms, conference space, and a 24-hour business center.
Pool
Parking included

Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $126 total per night
$126 total
Dec 28 - Dec 29
Total with taxes and fees
At Fairfield Inn & Suites Strasburg Shenandoah Valley, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. A stay here includes free parking. The 24-hour front desk has staff standing by to help with securing valuables and dry cleaning/laundry. Additional amenities include a 24-hour business center, coffee/tea in a common area, and express check-out.
Pool
Breakfast included

Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $82 total per night
$82 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Quality Inn Winchester features a gym, free WiFi in public areas, and meeting rooms. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help secure valuables, and answer any questions about the accommodations. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a computer station.
Pool
Breakfast included

Holiday Inn Express Hotel & Suites Winchester by IHG
142 Foxridge Ln Winchester VA
Free Cancellation
$107 nightly
The price is $116 total per night
$116 total
Jan 21 - Jan 22, 2026
Total with taxes and fees
At Holiday Inn Express Hotel & Suites Winchester by IHG, guests enjoy an indoor pool, a gym, and free WiFi in public areas. Free parking is included with your stay. Front-desk staff can answer questions 24/7, and assist with securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include a hot tub, meeting rooms, and a 24-hour business center.
Pool
Hot Tub

Baymont by Wyndham Front Royal Near Shenandoah National Park
10 S Commerce Ave Front Royal VA
Free Cancellation
Reserve now, pay when you stay
$55 nightly
The price is $61 total per night
$61 total
Dec 29 - Dec 30
Total with taxes and fees
Renovated in 2020, Baymont by Wyndham Front Royal Near Shenandoah National Park offers a gym, free WiFi in public areas, and a business center. Free parking is included with your stay. The front desk is staffed 24 hours a day to help with luggage storage and securing valuables. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a computer station.
Pool
Breakfast included
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.
Winchester hotels essential information
Accommodation | 2,026 hotels |
|---|---|
Lowest Price | $61 |
Highest Price | $143 |
Popular hotels | Country Inn & Suites by Radisson, Winchester, VA, The George Washington Hotel, A Wyndham Grand Hotel, Spark by Hilton Winchester, La Quinta Inn & Suites by Wyndham Winchester, DoubleTree by Hilton Front Royal Blue Ridge Shadows, Twi-Lite Inn, Hampton Inn Front Royal, Travelodge by Wyndham Winchester, Sleep Inn & Suites Winchester near University, Hilton Garden Inn Winchester, Holiday Inn Winchester Se-Historic Gateway by IHG, Fairfield Inn & Suites Strasburg Shenandoah Valley, Quality Inn Winchester, Holiday Inn Express Hotel & Suites Winchester by IHG, Baymont by Wyndham Front Royal Near Shenandoah National Park |
Recent Hotels with Pool Reviews

Comfort Inn & Suites Winchester
5/5 Excellent
"We have stayed here many times on our way to Massachusetts and find it perfect every time."
A verified traveler from Gainesville stayed at Comfort Inn & Suites Winchester
Posted 2 days ago
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