Old Town Winchester Hotels near Winchester

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

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, (1004)
"Great hotel!"
United States
CHARLES
The price is P7,450
P8,441 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The George Washington Hotel, A Wyndham Grand Hotel

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
21.9 km from Old Town Winchester
9.0 out of 10, Wonderful, (1000)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is P5,740
P6,331 total
includes taxes & fees
Jan 6 - Jan 7, 2026
DoubleTree by Hilton Front Royal Blue Ridge Shadows

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
25 km from Old Town Winchester
9.0 out of 10, Wonderful, (1005)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is P6,705
P7,462 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hampton Inn Front Royal

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
29.3 km from Old Town Winchester
9.6 out of 10, Exceptional, (440)
"Excellent accommodations and breakfast. "
United States
William
The price is P9,911
P11,199 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Carriage Inn B&B

The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino
3.0 star property
30 km from Old Town Winchester
8.6 out of 10, Excellent, (530)
"Friendly staff, comfortable bed, convenient location "
United States
Kourtney
The price is P7,058
P8,494 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Inn at Charles Town - Hollywood Casino

TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
24.4 km from Old Town Winchester
9.6 out of 10, Exceptional, (558)
"Excellent staff, clean rooms, convenient location right next to grocery stores and restaurants. "
United States
Carla
The price is P6,941
P7,774 total
includes taxes & fees
Jan 4 - Jan 5, 2026
TownePlace Suites by Marriott Front Royal

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
2.9 km from Old Town Winchester
9.2 out of 10, Wonderful, (2242)
"Staff is very pleasant and personable. "
United States
Julie
The price is P5,804
P6,315 total
includes taxes & fees
Jan 5 - Jan 6, 2026
La Quinta Inn & Suites by Wyndham Winchester

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
14.1 km from Old Town Winchester
9.6 out of 10, Exceptional, (175)
"This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. "
United States
DONNA
The price is P13,471
P14,858 total
includes taxes & fees
Jan 4 - Jan 5, 2026
L'Auberge Provencale Inn & Restaurant

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
5.3 km from Old Town Winchester
9.4 out of 10, Exceptional, (789)
"Great staff, very clean room with a good breakfast "
United States
Jim
The price is P6,300
P6,854 total
includes taxes & fees
Jan 5 - Jan 6, 2026
SpringHill Suites by Marriott Winchester

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
2.1 km from Old Town Winchester
8.8 out of 10, Excellent, (514)
"Great hotel"
United States
DONNA D
The price is P5,934
P6,723 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hilton Garden Inn Winchester

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
2.9 km from Old Town Winchester
9.0 out of 10, Wonderful, (807)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is P5,443
P5,922 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Fairfield Inn & Suites by Marriott Winchester

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
3.1 km from Old Town Winchester
9.0 out of 10, Wonderful, (923)
"Easy check in, friendly staff, clean and quiet room. Location convenient to store."
United States
Brenda
The price is P6,286
P6,839 total
includes taxes & fees
Jan 30 - Jan 31, 2026
Courtyard by Marriott Winchester

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
2.1 km from Old Town Winchester
9.2 out of 10, Wonderful, (852)
"The room was clean, and the breakfast was plentiful. The staff was very friendly and helpful. This was the quietest stay I've had on my trips to Wincheater."
United States
Jay
The price is P6,214
P7,041 total
includes taxes & fees
Jan 30 - Jan 31, 2026
Hampton Inn Winchester N/Conference Center, VA

Hillbrook Inn

Hillbrook Inn
4.0 star property
21.7 km from Old Town Winchester
8.6 out of 10, Excellent, (671)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
United States
Nataliya
The price is P9,353
P11,946 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hillbrook Inn

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
27.8 km from Old Town Winchester
8.2 out of 10, Very Good, (542)
"Clean, comfortable room. Staff was nice and I really enjoyed my stay. Motel was in a high traffic area, but still a quiet stay"
United States
Daniel
The price is P3,647
P4,059 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Twi-Lite Inn

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
12.4 km from Old Town Winchester
8.2 out of 10, Very Good, (808)
"Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. "
United States
Rose
The price is P4,353
P4,736 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express Winchester South-Stephens City by IHG

Travelodge By Wyndham Charles Town/Harpers Ferry

Travelodge By Wyndham Charles Town/Harpers Ferry
2.0 star property
29.5 km from Old Town Winchester
6.8 out of 10, (265)
"Room was very clean and quiet!"
United States
Mary ann
The price is P3,750
P4,238 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Travelodge By Wyndham Charles Town/Harpers Ferry

Wayside Inn

Wayside Inn
3.5 star property
19.8 km from Old Town Winchester
9.2 out of 10, Wonderful, (419)
"Historic inn. "
United States
Anonymous traveler
The price is P4,235
P5,259 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Wayside Inn

TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
3.0 star property
3 km from Old Town Winchester
8.8 out of 10, Excellent, (482)
"Nice place to stay. Great staff and breakfast."
United States
Stormy
The price is P6,300
P6,854 total
includes taxes & fees
Dec 31 - Jan 1, 2026
TownePlace Suites by Marriott Winchester

Relax Inn Motel

Relax Inn Motel
2.0 star property
27.6 km from Old Town Winchester
8.2 out of 10, Very Good, (259)
"Clean, and nice rooms, friendly staff"
United States
James
The price is P3,995
P4,446 total
includes taxes & fees
Jan 30 - Jan 31, 2026
Relax Inn Motel
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 and neighborhoods for the activities you enjoy most.

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

Find out more about Old Town Winchester

Top reasons to visit Old Town Winchester

  • Historic Charm: Stroll through Old Town Winchester's picturesque streets, lined with historic buildings and charming shops.
  • Outdoor Adventures: Enjoy scenic experiences in recreational areas and picturesque lakes, perfect for nature enthusiasts.
  • Cultural Experiences: Participate in walking tours to discover the rich history and heritage of the area.
  • Family-Friendly Activities: Find a range of activities suitable for all ages, ensuring a memorable experience for families.
  • Diverse Accommodations: Choose from historic hotels to modern lodgings, catering to various preferences and needs.

Find great hotels near Old Town Winchester

Discover a range of delightful hotel accommodations in Old Town Winchester, Virginia, perfect for your getaway. From historic hotels that capture the area's rich heritage to modern lodgings offering pet-friendly and LGBTQIA-welcoming experiences, there's something for everyone. Whether you seek business-friendly options or charming agritourism properties, Old Town Winchester has it all, including the renowned Wyndham Hotel nearby for a comfortable stay.

  • La Quinta Inn & Suites by Wyndham Winchester: Nestled 3.2km from Old Town Winchester, La Quinta Inn & Suites offers a welcoming atmosphere for all travellers, particularly those seeking an LGBTQIA-friendly environment. This hotel is ideal for business and leisure guests alike, and it proudly caters to pet owners with specific amenities. Enjoy spacious rooms equipped for comfort, alongside pet-friendly policies that allow dogs and cats. Guests can take advantage of complimentary breakfast and Wi-Fi, ensuring a convenient stay that meets both professional and personal needs.
  • Red Roof Inn Winchester, VA: Just 3.2km from the charming streets of Old Town Winchester, Red Roof Inn is a family-friendly haven that embraces an LGBTQIA-welcoming atmosphere. Perfect for families travelling with children, the hotel offers complimentary cribs and other child-friendly amenities. The pet-friendly policy allows guests to bring their furry companions with ease. Expect comfortable rooms and a range of services that cater to both adults and children alike, making it a great choice for those seeking a home-like experience during their stay.
  • Country Inn & Suites by Radisson, Winchester, VA: Situated 8.0km from Old Town Winchester, this 3-star hotel is perfect for families, business travellers, and pet owners. Country Inn & Suites blends comfort and convenience, featuring amenities designed for children, including complimentary cribs. The pet-friendly policy, offering food and water bowls, ensures your furry friends feel at home. Guests can unwind in spacious rooms, enjoy a complimentary breakfast, and take advantage of the business centre, making it a versatile choice for any type of traveller.

Where to stay near Old Town Winchester

Old Town Winchester offers a delightful blend of history and charm, perfect for outdoor enthusiasts and families alike. Stroll through its picturesque streets lined with local shops and immerse yourself in the friendly atmosphere. Nearby attractions enhance your experience with stunning scenery and rich historical significance. Whether you're exploring the vibrant urban life or enjoying the serene surroundings, Old Town Winchester promises a memorable vacation for every traveller.

  • Winchester: Nestled in the picturesque Shenandoah Valley, Winchester is a vibrant city rich in history and natural beauty. With Old Town Winchester as its centrepiece, the city offers a blend of outdoor adventures and scenic views. Visitors can explore numerous recreational areas, enjoy educational attractions, and even partake in skiing during the winter months. Notable nearby landmarks include national parks and serene lakes, making Winchester an ideal destination for those seeking both adventure and relaxation.
  • Winchester Historic District: Just 322m from Old Town Winchester, the Historic District is a charming neighbourhood that showcases the city’s rich heritage. The area attracts visitors year-round, particularly during the summer and autumn months. Here, you can indulge in outdoor activities, visit golf courses, and appreciate the local architecture. Proximity to national parks and historic colleges enhances the allure of this district, allowing travellers to immerse themselves in both nature and history.
  • College Park: Located approximately 3.2km from Old Town Winchester, College Park is a quaint village that offers a delightful escape. The area boasts a variety of recreational spaces, shopping centres, and vibrant shopping areas, making it a perfect spot for leisure and exploration. Like its neighbouring areas, College Park sees a steady flow of visitors throughout the year, particularly during the warmer months. With national parks and a visitor centre nearby, it provides an excellent base for those wishing to discover the natural beauty of the region.

Things to do in and around Old Town Winchester

Old Town Winchester offers an array of outdoor adventures and scenic experiences for visitors. Explore historic sites through walking tours, indulge in shopping at local centres, and enjoy recreational areas. For a comprehensive experience, consider a travel itinerary that highlights activities and attractions in Winchester, ensuring you capture the essence of this charming town.

Shopping

Located a mile from Old Town Winchester, Nalls Farm Market offers fresh produce and local goods. Nearby, Apple Valley Square Shopping Center and Northside Station Shopping Center feature a variety of shops, perfect for finding unique gifts in a vibrant, family-friendly atmosphere.

Recreation

At Rock Harbor Golf Course, immerse yourself in outdoor sports just 3.2km from Old Town Winchester, perfect for a refreshing game amidst scenic views. For relaxation, Jim Barnett Park, located 1.4km away, offers tranquil spaces, while Appleland Sports Center, 9.7km away, promotes wellness through various recreational activities.

Adventure

Experience the thrill of racing at Summit Point Motorsports Park, located 17.7km from Old Town Winchester, where adrenaline and speed meet. Alternatively, enjoy a fun-filled day of paintball at North Mountain Paintball, also 17.7km away, perfect for adventure enthusiasts seeking excitement and teamwork.

For a family-oriented outdoor experience, head to Watermelon Park Campground, situated 20.9km from Old Town Winchester, where you can camp under the stars and embrace nature's beauty with loved ones.

Nightlife

Experience the vibrant nightlife in Old Town Winchester by catching a show at Bright Box Theater or Winchester Little Theater, both offering a mix of romance and culture. For a family-friendly outing, consider visiting Morgan County Observatory, where you can enjoy the wonders of the cosmos.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Old Town Winchester

For a budget-friendly visit to Old Town Winchester, consider travelling between January and March when accommodation prices are lower. Tuesdays are generally the cheapest days to stay, while Saturdays tend to be the most costly. Utilise Expedia's search tool to filter options by price and take advantage of package deals that combine hotels, flights, and activities. Additionally, keep an eye out for free activities, beverage discounts, and last-minute deals to further enhance your savings during your trip.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Old Town Winchester are January to March, where the prices are slightly lower. This is in comparison to May to June and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Old Town Winchester is Tuesday. The most expensive day to stay around Old Town Winchester is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia's search tool to refine your choices, taking into account your budget, desired location, and preferred hotel type. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Old Town Winchester with your flights and activities through an Expedia package.

Find the best attractions near Old Town Winchester

Old Town Winchester offers a delightful blend of outdoor adventure and historic charm, making it ideal for a scenic vacation. Visitors can explore historic houses, picturesque lakes, and notable historic sites. The area is perfect for those seeking cultural experiences and family-friendly activities. Don't miss the charming old town, vibrant historic downtown, the Old Town Winchester walking mall, and nearby museums for an enriching experience.

  • Abrams Creek Wetlands Preserve: Experience the tranquility of nature at this eco-friendly reserve, where you can explore scenic trails, observe diverse wildlife, and enjoy a peaceful retreat from urban life.
  • Shenandoah University: Immerse yourself in the rich cultural atmosphere of this historic university, renowned for its beautiful architecture and vibrant campus life, offering a glimpse into local educational heritage.
  • Museum of the Shenandoah Valley: Delve into the region's history and art at this captivating museum, which showcases a variety of exhibits, including local artefacts and fine art, all set in a stunning landscape.

Best time to go to Old Town Winchester

The best time to visit Old Town Winchester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.3°F (-0.4°C)Light RainMostly SunnySlightly LowSlightly Low
February34.7°F (1.5°C)Light RainMostly SunnySlightly LowSlightly Low
March42.3°F (5.7°C)Light RainMostly SunnyAverageSlightly Low
April52.9°F (11.6°C)Light RainMostly SunnyAverageAverage
May62.4°F (16.9°C)Light RainMostly SunnyAverageSlightly High
June70.9°F (21.6°C)Light RainMostly SunnyAverageSlightly High
July75.9°F (24.4°C)Light RainMostly SunnySlightly HighAverage
August73.8°F (23.2°C)Light RainMostly SunnySlightly HighAverage
September66.9°F (19.4°C)Light RainMostly SunnyAverageAverage
October55.8°F (13.2°C)Light RainMostly SunnySlightly HighSlightly High
November43.5°F (6.4°C)Light RainMostly SunnyAverageAverage
December36.7°F (2.6°C)Light RainMostly SunnySlightly LowAverage

The nearest major airports for your trip to Old Town Winchester

Accessing Old Town Winchester is convenient via its nearby airports. Washington Dulles International Airport (IAD) is located 67.6km away, with excellent hotels such as the Hyatt Regency Dulles, Hilton Washington Dulles Airport, and The Westin Washington Dulles Airport, all within 3.2km of the airport. Hagerstown Regional Airport (HGR) is 69.2km distant, with options like Springhill Suites by Marriott and Country Inn & Suites, both 9.7km away. For the closest option, Eastern West Virginia Regional Airport (MRB) is just 29.0km away, with comfortable stays available at The Carriage Inn B&B and Home2 Suites by Hilton Martinsburg, both within 6.4km of the airport.

Frequently asked questions

What is Old Town Winchester like?
Old Town Winchester is a historic neighborhood known for its array of dining options. Are you looking for Old Town Winchester travel tips? Be sure to check out Bright Box Theater and Shenandoah Valley Discovery Museum while you're in the neighborhood.
Where is the best place to stay in Old Town Winchester?
Based on Expedia customer reviews, The George Washington Hotel, A Wyndham Grand Hotel is the highest ranked property in Old Town Winchester. This hotel offers a full-service spa and 2 restaurants.
How many hotels can I expect to find in the Old Town Winchester area?
With 11 Expedia hotels and other accommodations in Old Town Winchester to choose from, this is a good starting point for exploring the greater Winchester area.
If I need to cancel my hotel reservation in Old Town Winchester, will I receive a refund?
Yes, most hotel bookings are fully refundable if cancelled prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you booked a non-refundable reservation, it may still be possible to cancel it and get a refund within 24 hours of your booking. Plug in your dates, click on "Search", then filter by "fully refundable" to get top deals in Old Town Winchester.
What is there to do around this Winchester neighborhood?
Sights like Bright Box Theater and Old Court House Civil War Museum can be part of your cultural tour of Old Town Winchester. Shenandoah Valley Discovery Museum and Handley Regional Library are some other stops to visit in the neighborhood. A few places to visit in the area around Old Town Winchester include George Washington's Office, Mt Hebron Cemetery, and Winchester Little Theater. When you're sightseeing in Winchester, Stonewall Jackson's Headquarters and Patsy Cline Historic House are also worth a stop.