Historical Hotels in Winchester, VA
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Featured Winchester Historic Hotels

Wayside Inn
7783 Main St Middletown VA
$89 nightly
The price is $98 total per night
$98 total
Dec 24 - Dec 25
Total with taxes and fees
Wayside Inn features free WiFi in public areas, coffee in a common area, and a meeting room. You can take advantage of free parking if you drive. Additional amenities include a library, express check-out, and a terrace.
Parking included
Free WiFi

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 30 - Dec 31
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

Hotel Strasburg
213 S. Holliday Street Strasburg VA
Hotel Strasburg features free WiFi in public areas, conference space, and coffee in a common area. If you drive, put free parking to good use. The 24-hour front desk has multilingual staff ready to help with tours or tickets, and answer any questions about the area. Other amenities at this historic hotel include free newspapers, a TV in a common area, and a garden.
Breakfast included
Pet friendly

Fairfield Inn & Suites by Marriott Winchester
250 Front Royal Pike Winchester VA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $101 total per night
$101 total
Dec 25 - Dec 26
Total with taxes and fees
Guests staying at Fairfield Inn & Suites by Marriott Winchester enjoy an indoor pool, a gym, and free WiFi in public areas. There's free parking and limo/town car service. The 24-hour front desk has staff standing by to help with securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include meeting rooms, conference space, and a 24-hour business center.
Pool
Breakfast included

Red Roof Inn Winchester, VA
991 Millwood Pike Winchester VA
Free Cancellation
Reserve now, pay when you stay
$69 nightly
The price is $75 total per night
$75 total
Dec 28 - Dec 29
Total with taxes and fees
Renovated in 2024, Red Roof Inn Winchester, VA offers free WiFi in public areas, coffee in a common area, and express check-in. 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 express check-out, laundry facilities, and a TV in a common area.
Pet friendly
Parking included

Hampton Inn Winchester N/Conference Center, VA
1204 Berryville Avenue Winchester VA
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $120 total per night
$120 total
Dec 30 - Dec 31
Total with taxes and fees
At Hampton Inn Winchester N/Conference Center, VA, guests have access to a gym, free WiFi in public areas, and meeting rooms. If you drive, put free parking to good use. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, securing valuables, and luggage storage. Additional amenities include a conference center, a 24-hour business center, and a seasonal outdoor pool.
Pool
Breakfast included

Motel 6 Front Royal, VA
141 West 15th Street Front Royal VA
Free Cancellation
Reserve now, pay when you stay
$57 nightly
The price is $63 total per night
$63 total
Dec 24 - Dec 25
Total with taxes and fees
Guests staying at Motel 6 Front Royal, VA enjoy free WiFi in public areas, laundry facilities, and a vending machine. If you plan to drive, free parking is available. The 24-hour front desk has multilingual staff ready to assist with sightseeing, directions, and local dining recommendations. Additional amenities include a TV in a common area, a picnic area, and a garden.
Pet friendly
Parking included

Clarion Inn & Conference Center
711 Millwood Avenue, 711 Winchester VA
Guests of Clarion Inn & Conference Center enjoy a gym, free WiFi in public areas, and meeting rooms. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to assist with sightseeing, directions, and local dining recommendations. Additional amenities include conference space, a business center, and a seasonal outdoor pool.
Pool
Pet friendly

Hampton Inn Winchester-University/Mall Area
640 East Jubal Early Drive Winchester VA
Free Cancellation
Reserve now, pay when you stay
$102 nightly
The price is $115 total per night
$115 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
At Hampton Inn Winchester-University/Mall Area, guests enjoy features like an outdoor pool, a gym, and free WiFi in public areas. If you drive, take advantage of free parking. The 24-hour front desk has staff standing by to help with dry cleaning/laundry and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a 24-hour business center, a seasonal outdoor pool, and coffee/tea in a common area.
Pool
Breakfast included

Motel 6 Winchester, VA
2951 Valley Avenue Winchester VA
Free Cancellation
Reserve now, pay when you stay
$68 nightly
The price is $77 total per night
$77 total
Dec 24 - Dec 25
Total with taxes and fees
Motel 6 Winchester, VA features free WiFi in public areas and a vending machine. You can take advantage of free parking if you drive. The 24-hour front desk has staff always at the ready.
Pet friendly
Parking included

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

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

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

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
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 | $63 |
Highest Price | $143 |
Popular hotels | Wayside Inn, The George Washington Hotel, A Wyndham Grand Hotel, Hotel Strasburg, Fairfield Inn & Suites by Marriott Winchester, Red Roof Inn Winchester, VA, Hampton Inn Winchester N/Conference Center, VA, Motel 6 Front Royal, VA, Clarion Inn & Conference Center, Hampton Inn Winchester-University/Mall Area, Motel 6 Winchester, VA, Spark by Hilton Winchester, Quality Inn Winchester, Holiday Inn Express Hotel & Suites Winchester by IHG, Holiday Inn Winchester Se-Historic Gateway by IHG, Country Inn & Suites by Radisson, Winchester, VA |
Recent Historic Hotels 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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