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 16 - Dec 17
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.

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 22 - Dec 23
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.

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 17 - Dec 18
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.

Red Roof Inn Winchester, VA
991 Millwood Pike Winchester VA
Free Cancellation
Reserve now, pay when you stay
$60 nightly
The price is $66 total per night
$66 total
Jan 1 - Jan 2, 2026
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
$103 nightly
The price is $117 total per night
$117 total
Dec 22 - Dec 23
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
$60 nightly
The price is $67 total per night
$67 total
Dec 16 - Dec 17
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.

Hampton Inn Winchester-University/Mall Area
640 East Jubal Early Drive Winchester VA
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $112 total per night
$112 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.

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 16 - Dec 17
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.

Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $85 total per night
$85 total
Jan 4 - Jan 5, 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
$104 nightly
The price is $113 total per night
$113 total
Dec 18 - Dec 19
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
$73 nightly
The price is $79 total per night
$79 total
Dec 23 - Dec 24
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.

Country Inn & Suites by Radisson, Winchester, VA
141 Kernstown Commons Blvd Winchester VA
Free Cancellation
$84 nightly
The price is $91 total per night
$91 total
Jan 4 - Jan 5, 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.
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 | 2,036 hotels |
|---|---|
Lowest Price | $66 |
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

Microtel Inn & Suites by Wyndham Winchester
5/5 Excellent
"This was either the 3rd or 4th time for me staying at this hotel over the last few years and the hotel pretty much looks the same. Looks clean and doesn't seem to have much normal wear and tear that most hotels have. Looks as new as it did the first time I stayed. "
A verified traveler stayed at Microtel Inn & Suites by Wyndham Winchester
Posted 4 days ago
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