Historical Hotels in Winchester, VA
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Featured Winchester Historic Hotels

Wayside Inn
7783 Main St, Middletown, VA
$114 nightly
The price is $126 total per night
$126 total
Aug 3 - Aug 4
Total includes 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, a terrace, and a ballroom.
Parking included
Free WiFi

The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
$127 nightly
The price is $144 total per night
$144 total
Jul 31 - Aug 1
Total includes 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 luggage storage, dry cleaning/laundry, and concierge services. 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, wedding services, and a TV in a common area.
Breakfast included
Pet friendly

Fairfield Inn & Suites by Marriott Winchester
250 Front Royal Pike, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$97 nightly
The price is $105 total per night
$105 total
Aug 3 - Aug 4
Total includes 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
$70 nightly
The price is $76 total per night
$76 total
Aug 3 - Aug 4
Total includes 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
$110 nightly
The price is $124 total per night
$124 total
Aug 10 - Aug 11
Total includes 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 luggage storage, tours or tickets, and securing valuables. 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
$65 nightly
The price is $72 total per night
$72 total
Jul 31 - Aug 1
Total includes taxes and fees
Guests staying at Motel 6 Front Royal, VA enjoy free WiFi in public areas, laundry facilities, and a garden. 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 vending machine, a fireplace in the lobby, and a picnic area.
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
$117 nightly
The price is $132 total per night
$132 total
Aug 3 - Aug 4
Total includes 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 luggage storage and dry cleaning/laundry. 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
$64 nightly
The price is $73 total per night
$73 total
Aug 4 - Aug 5
Total includes 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
$94 nightly
The price is $106 total per night
$106 total
Aug 24 - Aug 25
Total includes 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
1601 Martinsburg Pike, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $92 total per night
$92 total
Aug 7 - Aug 8
Total includes 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
$126 nightly
The price is $137 total per night
$137 total
Aug 3 - Aug 4
Total includes 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 dry cleaning/laundry, luggage storage, and securing valuables. 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
$92 nightly
The price is $100 total per night
$100 total
Aug 3 - Aug 4
Total includes 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 luggage storage, dry cleaning/laundry, 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
$95 nightly
The price is $104 total per night
$104 total
Aug 3 - Aug 4
Total includes 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 | 1,994 hotels |
---|---|
Lowest Price | $72 |
Highest Price | $144 |
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, 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

Country Inn & Suites by Radisson, Winchester, VA
5/5 Excellent
"Justin made check in easy and was amenable to moving me up a floor.
He has awesome people skills! Very personable."
A verified traveler stayed at Country Inn & Suites by Radisson, Winchester, VA
Posted 2 days ago
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