The Courthouse in Winchester, Virginia.

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Our top choices for Old Town Winchester hotels

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1,000 reviews)
"Clean charming place to stay in the area "
United States
Elizabeth
The price is £105
includes taxes & fees
12 Jul - 13 Jul
The George Washington Hotel, A Wyndham Grand Hotel

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
4.8 mi from Old Town Winchester
9.4 out of 10, Exceptional, (1,122 reviews)
"Decent accommodations, friendly staff."
United States
Juliet
The price is £84
includes taxes & fees
28 Jun - 29 Jun
Comfort Inn & Suites Winchester

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
1.3 mi from Old Town Winchester
9.2 out of 10, Wonderful, (905 reviews)
"The room was very clean and the front desk staffs were very nice."
United States
Angelina
The price is £98
includes taxes & fees
1 Jul - 2 Jul
Hampton Inn Winchester N/Conference Center, VA

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
1.8 mi from Old Town Winchester
9.2 out of 10, Wonderful, (2,270 reviews)
"Breakfast was great and the staff were very nice!"
United States
Madeline
The price is £90
includes taxes & fees
1 Jul - 2 Jul
La Quinta Inn & Suites by Wyndham Winchester

Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
2.0 star property
18.5 mi from Old Town Winchester
8.6 out of 10, Excellent, (1,004 reviews)
"Wonderful place to stay"
United States
Jeremiah
The price is £65
includes taxes & fees
7 Jul - 8 Jul
Rodeway Inn & Suites Charles Town

Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry
2.0 star property
18.4 mi from Old Town Winchester
7.8 out of 10, Good, (1,001 reviews)
"Best breakfast week had all week at a hotel. Friendly staff & clean rooms."
United States
Lauren
The price is £57
includes taxes & fees
7 Jul - 8 Jul
Days Inn by Wyndham Charles Town/Harpers Ferry

Hillbrook Inn

Hillbrook Inn
4.0 star property
13.5 mi from Old Town Winchester
8.6 out of 10, Excellent, (679 reviews)
"Lovely Luxury with a spacious sunset suite. Very comfortable bed and sofa. Wish there were one or more sofa tables. staff were delightful, will definitely come again. Please add a cafe for guests not wanting a large expensive dinner. Breakfast Food was very good. Kitchen well equipped for beverage and snack storage, and very clean."
United States
Margaret
The price is £135
includes taxes & fees
12 Jul - 13 Jul
Hillbrook Inn

Travelodge By Wyndham Charles Town/Harpers Ferry

Travelodge By Wyndham Charles Town/Harpers Ferry
2.0 star property
18.3 mi from Old Town Winchester
7.2 out of 10, Good, (302 reviews)
"Everything was great"
United States
Maurice
The price is £58
includes taxes & fees
28 Jun - 29 Jun
Travelodge By Wyndham Charles Town/Harpers Ferry

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
8.7 mi from Old Town Winchester
9.6 out of 10, Exceptional, (178 reviews)
"Everything about this special place is incredible."
United States
James
The price is £187
includes taxes & fees
28 Jun - 29 Jun
L'Auberge Provencale Inn & Restaurant

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
1.3 mi from Old Town Winchester
9.0 out of 10, Wonderful, (1,004 reviews)
"Excellent hotel, very clean, nice beds."
United States
Sarat
The price is £78
includes taxes & fees
1 Jul - 2 Jul
Spark by Hilton Winchester

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
2.7 mi from Old Town Winchester
9.4 out of 10, Exceptional, (1,004 reviews)
"Clean, quiet, great breakfast! Perfect for our quick stay in Winchester."
United States
Hannah
The price is £83
includes taxes & fees
6 Jul - 7 Jul
Quality Inn Winchester

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
3.3 mi from Old Town Winchester
9.4 out of 10, Exceptional, (863 reviews)
"Staff was very helpful, room was better than expected, pool was fantastic. Nice fitness center too."
United States
Chris
The price is £94
includes taxes & fees
2 Jul - 3 Jul
SpringHill Suites by Marriott Winchester

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
15.6 mi from Old Town Winchester
9.0 out of 10, Wonderful, (1,007 reviews)
"Clean , close to National park"
United States
Robert
The price is £110
includes taxes & fees
6 Jul - 7 Jul
Hampton Inn Front Royal

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
2.6 mi from Old Town Winchester
9.2 out of 10, Wonderful, (1,458 reviews)
"Excellent stay"
United States
Michael
The price is £77
includes taxes & fees
12 Jul - 13 Jul
Microtel Inn & Suites by Wyndham Winchester

Relax Inn Motel

Relax Inn Motel
2.0 star property
17.2 mi from Old Town Winchester
8.4 out of 10, Very good, (283 reviews)
"The owners/managers are delightful. The room was very nice with excellent bedding. I look forward to staying there again "
United States
Sarah
The price is £57
includes taxes & fees
25 Jun - 26 Jun
Relax Inn Motel

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
7.7 mi from Old Town Winchester
8.2 out of 10, Very good, (860 reviews)
" Breakfast was delicious!"
Canada
Betty
The price is £82
includes taxes & fees
28 Jun - 29 Jun
Holiday Inn Express Winchester South-Stephens City by IHG

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
2.7 mi from Old Town Winchester
9.2 out of 10, Wonderful, (981 reviews)
"It was great for a stay."
United States
Sheree
The price is £65
includes taxes & fees
1 Jul - 2 Jul
TRU By Hilton Winchester

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
4.7 mi from Old Town Winchester
8.8 out of 10, Excellent, (1,000 reviews)
"Location is great, near popular restaurants. Bed was so comfortable! Staff was very friendly and helpful."
United States
Brenda
The price is £80
includes taxes & fees
19 Jul - 20 Jul
Country Inn & Suites by Radisson, Winchester, VA

TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
15.1 mi from Old Town Winchester
9.6 out of 10, Exceptional, (584 reviews)
"Great location to explore the Shenandoah mountains . Lots of shops and eateries."
United States
katherine
The price is £118
includes taxes & fees
29 Jun - 30 Jun
TownePlace Suites by Marriott Front Royal

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
18.2 mi from Old Town Winchester
9.6 out of 10, Exceptional, (449 reviews)
"Lovely inn with gracious hosts and fabulous breakfast. "
United States
Megan
The price is £126
includes taxes & fees
30 Jun - 1 Jul
The Carriage Inn B&B
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.

Where to stay in Old Town Winchester

Find the best Old Town Winchester areas for the activities you enjoy most. Learn more about Old Town Winchester
Learn more about Old Town Winchester

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater.

Top Old Town Winchester Hotel Reviews

Frequently asked questions

What are the best hotels in Old Town Winchester that travellers recommend?
For an excellent hotel in Old Town Winchester that travellers consistently recommend, consider The George Washington Hotel, A Wyndham Grand Hotel.

This 3.5-star hotel, with an outstanding 9.4 rating, is praised by guests for its comfortable and clean rooms, as well as its friendly and helpful staff. The hotel offers convenient amenities such as valet parking, an indoor pool, and accessible fitness facilities, some of which are available 24 hours a day or offer discounts at nearby locations. Its location is considered great, and guests appreciate the free and easy parking. The Bright Box Theater is just 0.3 km away, making it an ideal choice for those looking to enjoy local entertainment.
What are the best family hotels in Old Town Winchester?
For family-friendly accommodation in Old Town Winchester, The George Washington Hotel, A Wyndham Grand Hotel, is an excellent choice.

This 3.5-star hotel, with an impressive 9.4 rating, is highly regarded by families. Guests consistently mention the comfortable and clean rooms, along with the friendly and helpful staff. It offers free internet and WiFi, connecting rooms, and complimentary toiletries, which are all convenient for families. The hotel also provides free cribs upon request. Its location is considered great, and parking is free and easy. The George Washington Hotel is conveniently located near Bright Box Theater, just 0.3 km away, and Friendship Park is also within easy reach at 1.2 km.
What are the best spa hotels in Old Town Winchester?
For a highly-rated spa hotel in Old Town Winchester, The George Washington Hotel, A Wyndham Grand Hotel is an excellent choice.

This 3.5-star hotel, with an impressive 9.4 rating, offers a full-service spa with daily treatments and massage services, great for relaxation. Guests frequently praise the comfortable and clean rooms, the friendly and helpful staff, and the convenient location. Additionally, the hotel provides free internet and free WiFi, along with complimentary toiletries and free cribs upon request. Free and easy parking is also a welcome amenity.
When is the best time to go to Old Town Winchester?
The best time to go to Old Town Winchester is during the spring (April to May) or autumn (September to October) when the weather is pleasant and the town is particularly charming.

Spring brings blooming flowers and comfortable temperatures, great for strolling along the historic streets and enjoying outdoor dining. This is also when the famous Shenandoah Apple Blossom Festival takes place, usually in late April or early May, which fills the town with parades, music, and events. Couples often enjoy this time for its romantic feel and the chance to experience a lively local tradition.

Autumn offers crisp air and beautiful fall foliage, especially in late September and October. The cooler temperatures are ideal for exploring the walking mall and visiting nearby orchards for apple picking. Families will find this a lovely time to visit, with plenty of activities like pumpkin patches and corn mazes in the surrounding area, making for memorable day trips.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Old Town Winchester.
How can I save on a Old Town Winchester hotel booking with Expedia?
Members always get our best prices. Find our best Old Town Winchester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Old Town Winchester hotel?
Hotel prices in Old Town Winchester often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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