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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, (1,009 reviews)
" Try nice hotel and a great location. "
United States
Steven
The price is £102
includes taxes & fees
4 Jun - 5 Jun
The George Washington Hotel, A Wyndham Grand Hotel

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
18.9 mi from Old Town Winchester
7.6 out of 10, Good, (1,005 reviews)
"Location is right across the road from Spelunker's, the best casual restaurant in Virginia."
United States
Rachel
The price is £60
includes taxes & fees
11 May - 12 May
Super 8 by Wyndham Front Royal Near Shenandoah National Park

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, (1,032 reviews)
"Great location, clean rooms and friendly staff."
United States
Daniel
The price is £61
includes taxes & fees
31 May - 1 Jun
Spark by Hilton Winchester

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, (176 reviews)
"Everything about this special place is incredible."
United States
James
The price is £174
includes taxes & fees
11 May - 12 May
L'Auberge Provencale Inn & Restaurant

Hillbrook Inn

Hillbrook Inn
4.0 star property
13.5 mi from Old Town Winchester
8.6 out of 10, Excellent, (677 reviews)
"Wonderful staff, and fall cottage was lovely."
United States
Henrik
The price is £149
includes taxes & fees
11 May - 12 May
Hillbrook Inn

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, (1,006 reviews)
"Friendly staff clean and comfy"
United Kingdom
Helen
The price is £100
includes taxes & fees
25 May - 26 May
Hampton Inn Front Royal

Relax Inn Motel

Relax Inn Motel
2.0 star property
17.2 mi from Old Town Winchester
8.2 out of 10, Very good, (271 reviews)
"On my way back from shenendoah and Luray to dc place was fine "
United States
tara
The price is £53
includes taxes & fees
11 May - 12 May
Relax Inn Motel

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
7.0 out of 10, Good, (279 reviews)
"Basic accommodations, clean room, friendly staff, decent continental breakfast options. Overall, a very nice stay for the price range. "
United States
Kevin
The price is £53
includes taxes & fees
11 May - 12 May
Travelodge By Wyndham Charles Town/Harpers Ferry

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, (1,109 reviews)
"Very friendly front desk Quiet surroundings. Great restaurant nearby"
United States
Rosemary
The price is £84
includes taxes & fees
7 Jun - 8 Jun
Comfort Inn & Suites Winchester

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
1.9 mi from Old Town Winchester
9.0 out of 10, Wonderful, (974 reviews)
"Beautiful hotel!"
United States
David
The price is £85
includes taxes & fees
21 May - 22 May
Courtyard by Marriott Winchester

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, (576 reviews)
"Clean"
United States
Padmanabhan
The price is £104
includes taxes & fees
17 May - 18 May
TownePlace Suites by Marriott Front Royal

The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino
3.0 star property
18.7 mi from Old Town Winchester
8.6 out of 10, Excellent, (572 reviews)
"Very friendly staff in a great location and well maintained. Convenient shuttle to the casino. Staff was exceptionally friendly and helpful"
United States
Kevin
The price is £85
includes taxes & fees
13 May - 14 May
The Inn at Charles Town - Hollywood Casino

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
8.0 out of 10, Very good, (1,006 reviews)
"Definitely stay somewhere else"
United States
William
The price is £59
includes taxes & fees
7 Jun - 8 Jun
Days Inn by Wyndham Charles Town/Harpers Ferry

Wayside Inn

Wayside Inn
3.5 star property
12.3 mi from Old Town Winchester
9.2 out of 10, Wonderful, (429 reviews)
"Old building but clean and very comfortable. Perfect spot and price."
United States
Caroline
The price is £106
includes taxes & fees
12 May - 13 May
Wayside Inn

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, (447 reviews)
"Lovely inn with gracious hosts and fabulous breakfast. "
United States
Megan
The price is £128
includes taxes & fees
1 Jun - 2 Jun
The Carriage Inn B&B

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, (888 reviews)
"Location was excellent"
United States
Jennie
The price is £89
includes taxes & fees
17 May - 18 May
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, (2,282 reviews)
"Hotel was clean, staff were attentive and breakfast was good."
Canada
Sandra
The price is £93
includes taxes & fees
13 May - 14 May
La Quinta Inn & Suites by Wyndham Winchester

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
2.7 mi from Old Town Winchester
9.0 out of 10, Wonderful, (846 reviews)
"I'd vouch for them as if it was my Hotel, Very nice place to stay."
United States
Jhoan
The price is £90
includes taxes & fees
17 May - 18 May
TRU By Hilton Winchester

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
2.7 mi from Old Town Winchester
9.2 out of 10, Wonderful, (1,006 reviews)
"Great breakfast. Very clean. Parking was safe and easy. Staff was excellent!"
United States
Diane
The price is £71
includes taxes & fees
25 May - 26 May
Quality Inn 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, (1,007 reviews)
"Clean room, friendly staff. Fair breakfast…the bagels and muffins were old."
United States
Barbara
The price is £63
includes taxes & fees
25 May - 26 May
Rodeway Inn & Suites Charles Town
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 Shenandoah Valley Discovery Museum.

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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