Old Town Winchester Hotels near Winchester

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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, (1,001 reviews)
"Location of hotel is great for walking to restaurants and shops. "
United States
Paul
The price is P7,359
P8,337 total
includes taxes & fees
Apr 26 - Apr 27
The George Washington Hotel, A Wyndham Grand Hotel

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, (870 reviews)
"The staff was wonderful! "
United States
Jayne
The price is P6,446
P7,303 total
includes taxes & fees
Apr 18 - Apr 19
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
2.9 km from Old Town Winchester
9.2 out of 10, Wonderful, (2,268 reviews)
"Very nice would stay there again"
United States
John
The price is P6,613
P7,195 total
includes taxes & fees
Apr 5 - Apr 6
La Quinta Inn & Suites by Wyndham Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
7.8 km from Old Town Winchester
9.4 out of 10, Exceptional, (1,097 reviews)
"Overall a pleasant stay!"
United States
Mark
The price is P6,317
P6,873 total
includes taxes & fees
Apr 29 - Apr 30
Comfort Inn & Suites Winchester

Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
2.0 star property
29.7 km from Old Town Winchester
8.6 out of 10, Excellent, (1,004 reviews)
"Clean room, super friendly people, great breakfast, and the shuttle was awesome!"
United States
India
The price is P4,095
P4,627 total
includes taxes & fees
Apr 16 - Apr 17
Rodeway Inn & Suites Charles Town

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
7.0 out of 10, Good, (272 reviews)
"Decent continental breakfast. Night staff is friendly and helpful. Accessible. "
United States
David
The price is P3,840
P4,339 total
includes taxes & fees
Apr 6 - Apr 7
Travelodge By Wyndham Charles Town/Harpers Ferry

Hillbrook Inn

Hillbrook Inn
4.0 star property
21.7 km from Old Town Winchester
8.6 out of 10, Excellent, (676 reviews)
"Wonderful staff, and fall cottage was lovely."
United States
Henrik
The price is P10,781
P13,580 total
includes taxes & fees
Apr 5 - Apr 6
Hillbrook Inn

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
2.9 km from Old Town Winchester
9.0 out of 10, Wonderful, (831 reviews)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is P5,580
P6,071 total
includes taxes & fees
Apr 6 - Apr 7
Fairfield Inn & Suites by Marriott Winchester

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, (829 reviews)
"Beautiful hotel and room. Accessible room was perfect. Staff was friendly right from check-in. Would highly recommend this hotel to anyone who needs an accessible room. "
United States
Andrew
The price is P6,837
P7,439 total
includes taxes & fees
Apr 9 - Apr 10
SpringHill Suites by Marriott Winchester

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, (568 reviews)
"Clean room, friendly and helpful staff, good breakfast, I would stay again."
United States
Catherine
The price is P7,649
P8,557 total
includes taxes & fees
Apr 7 - Apr 8
TownePlace Suites by Marriott Front Royal

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
4.3 km from Old Town Winchester
9.2 out of 10, Wonderful, (1,001 reviews)
"Everything was perfect. Would highly recommend this hotel"
Canada
Phyllis
The price is P5,509
P5,994 total
includes taxes & fees
Apr 19 - Apr 20
Quality Inn Winchester

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
25 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,003 reviews)
"All the staff members were so nice and kind!! The hotel room I booked were very clean and spotless, and the breakfast was even fresh too!"
United States
Kenny
The price is P6,798
P7,566 total
includes taxes & fees
Apr 27 - Apr 28
Hampton Inn Front Royal

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
7.5 km from Old Town Winchester
8.8 out of 10, Excellent, (1,000 reviews)
"Very clean rooms and friendly staff."
United States
Christine
The price is P5,567
P6,057 total
includes taxes & fees
May 3 - May 4
Country Inn & Suites by Radisson, Winchester, VA

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, (950 reviews)
"Great location"
Canada
jim
The price is P6,444
P7,012 total
includes taxes & fees
Apr 20 - Apr 21
Courtyard 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, (262 reviews)
"On my way back from shenendoah and Luray to dc place was fine "
United States
tara
The price is P3,734
P4,156 total
includes taxes & fees
Apr 5 - Apr 6
Relax Inn Motel

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
2 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,000 reviews)
"Nice staff, clean with a convenient location make it a good choice for a stay in Winchester. "
United States
Mira
The price is P5,230
P5,926 total
includes taxes & fees
Apr 19 - Apr 20
Spark by Hilton Winchester

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
27.8 km from Old Town Winchester
8.2 out of 10, Very Good, (548 reviews)
"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 P4,517
P5,028 total
includes taxes & fees
Apr 5 - Apr 6
Twi-Lite Inn

Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry
2.0 star property
29.6 km from Old Town Winchester
8.0 out of 10, Very Good, (1,002 reviews)
"Very accessible to restaurants and stores"
United States
Scott
The price is P4,074
P4,603 total
includes taxes & fees
Apr 27 - Apr 28
Days Inn by Wyndham Charles Town/Harpers Ferry

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
3.0 star property
24.9 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,001 reviews)
"Asked for quiet floor after a long week of travels for work and he put me on the 4th floor Was super quiet , super clean and breakfast was decent,"
United States
angie
The price is P6,806
P7,575 total
includes taxes & fees
Apr 9 - Apr 10
Fairfield Inn & Suites Strasburg Shenandoah Valley

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
4.1 km from Old Town Winchester
9.2 out of 10, Wonderful, (1,460 reviews)
"Everything,room was amazing, staff so friendly, breakfast very good "
United States
Douglas Gary
The price is P5,396
P5,871 total
includes taxes & fees
Apr 26 - Apr 27
Microtel Inn & Suites by Wyndham Winchester
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 12 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 George Washington's Office are some other stops to visit in the neighborhood. A few places to visit in the area around Old Town Winchester include Handley Regional Library, 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.