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Old Town Winchester Hotels near Winchester

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Our top choices for Old Town Winchester hotels

1. 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, (1,005 reviews)
"We love to stay here every time we are in Winchester! Awesome pedestrian zone with lots of restaurants within walking distance. Great hotel."
United States
Elise
The price is P7,508
P8,506 total
includes taxes & fees
Aug 23 - Aug 24
The George Washington Hotel, A Wyndham Grand Hotel

2. 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, (921 reviews)
"The staff were very helpful and plesant Shamoia was great and ready to help with any needs."
United States
Brian
The price is P6,500
P7,365 total
includes taxes & fees
Aug 23 - Aug 24
Hampton Inn Winchester N/Conference Center, VA

3. 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, (2,266 reviews)
"Very nice clean hotel"
United States
chouaib
The price is P6,581
P7,325 total
includes taxes & fees
Aug 18 - Aug 19
La Quinta Inn & Suites by Wyndham Winchester

4. TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
4.4 km from Old Town Winchester
9.2 out of 10, Wonderful, (1,005 reviews)
"Great location and pleasant stay."
United States
Kelly
The price is P5,996
P6,674 total
includes taxes & fees
Aug 23 - Aug 24
TRU By Hilton Winchester

5. 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
7.8 out of 10, Good, (1,002 reviews)
"Dollar for dollar, this is the best hotel value in Charlestown, West Virginia. Conveniently located a short drive to and from Hollywood Casino, plus they have a shuttle back and forth. The rooms are perfectly fine, although still have a 1980’s look and feel. Ample parking. Nice free continental breakfast. This has been become my go-to hotel in Charlestown."
United States
James
The price is P4,156
P4,697 total
includes taxes & fees
Aug 26 - Aug 27
Days Inn by Wyndham Charles Town/Harpers Ferry

6. 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, (608 reviews)
"Will come back again. Very friendly staff"
United States
Christos
The price is P6,390
P7,772 total
includes taxes & fees
Aug 18 - Aug 19
The Inn at Charles Town - Hollywood Casino

7. 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, (1,008 reviews)
"Decent place to stay. Nothing fancy but room was clean and the shuttle to and from the casino was a nice benefit. I would stay here again."
United States
Duane
The price is P4,439
P5,016 total
includes taxes & fees
Sep 6 - Sep 7
Rodeway Inn & Suites Charles Town

8. Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
2 km from Old Town Winchester
9.2 out of 10, Wonderful, (1,007 reviews)
"Such a cute and clean hotel! A great place to stay if you need to go to Shenandoah University. Restaurants were within walking distance. The hotel also has a nice continental breakfast but if you’re wanting more there’s a Waffle House right outside the front door."
United States
Joscelyn
The price is P4,793
P5,430 total
includes taxes & fees
Sep 2 - Sep 3
Spark by Hilton Winchester

9. 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, (318 reviews)
"Worst place I’ve ever stayed!!!"
United States
Mike
The price is P3,917
P4,427 total
includes taxes & fees
Aug 18 - Aug 19
Travelodge By Wyndham Charles Town/Harpers Ferry

10. 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, (453 reviews)
"Amazing place with incredible history!"
United States
Andrea
The price is P10,353
P11,699 total
includes taxes & fees
Aug 18 - Aug 19
The Carriage Inn B&B

11. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
2.9 km from Old Town Winchester
9.2 out of 10, Wonderful, (913 reviews)
"Breakfast was great and very good price.would very much stay again."
United States
george
The price is P5,693
P6,337 total
includes taxes & fees
Aug 20 - Aug 21
Fairfield Inn & Suites by Marriott Winchester

12. Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
2.5 star property
2.1 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,001 reviews)
"We stay here on the way to NY ,great location ,close to I-81,"
United States
John
The price is P6,267
P7,100 total
includes taxes & fees
Aug 23 - Aug 24
Hampton Inn Winchester-University/Mall Area

13. 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, (1,435 reviews)
"Clean, friendly, close to highway, gas & food. Would definitely stay again while traveling through."
United States
Cheryl
The price is P5,408
P6,019 total
includes taxes & fees
Aug 30 - Aug 31
Microtel Inn & Suites by Wyndham Winchester

14. 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, (524 reviews)
"The staff was friendly, the room was clean, amenities were sufficient and comparable to similar hotels. We had a very nice stay here."
United States
Katherine
The price is P6,947
P7,732 total
includes taxes & fees
Aug 23 - Aug 24
TownePlace Suites by Marriott Winchester

15. Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
3.2 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,009 reviews)
"Rooms very clean with comfortable beds after a long day of driving!"
United States
Jennifer
The price is P5,715
P6,545 total
includes taxes & fees
Aug 23 - Aug 24
Holiday Inn Winchester Se-Historic Gateway by IHG

16. 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, (891 reviews)
"Clean, receptive staff, great breakfast."
United States
Michael
The price is P6,976
P7,764 total
includes taxes & fees
Sep 7 - Sep 8
SpringHill Suites by Marriott Winchester

17. Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
2.1 km from Old Town Winchester
9.0 out of 10, Wonderful, (544 reviews)
"Very nice property."
United States
Don
The price is P7,155
P8,107 total
includes taxes & fees
Aug 23 - Aug 24
Hilton Garden Inn Winchester

18. Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
2.9 km from Old Town Winchester
8.6 out of 10, Excellent, (1,073 reviews)
"Great staff, clean rooms and good breakfast."
United States
Jeffrey
The price is P4,240
P4,677 total
includes taxes & fees
Aug 18 - Aug 19
Travelodge by Wyndham Winchester

19. Quality Inn Winchester

Quality Inn Winchester
2.5 star property
4.3 km from Old Town Winchester
9.4 out of 10, Exceptional, (1,004 reviews)
"Nice breakfast, convenient location and helpful staff."
United States
Scott
The price is P5,171
P5,755 total
includes taxes & fees
Aug 23 - Aug 24
Quality Inn Winchester

20. Hillbrook Inn

Hillbrook Inn
4.0 star property
21.7 km from Old Town Winchester
8.6 out of 10, Excellent, (691 reviews)
"It was beautiful location. The staff was amazing and the food was excellent highly recommend."
United States
Cecile
The price is P9,156
P11,791 total
includes taxes & fees
Aug 20 - Aug 21
Hillbrook Inn
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 Shenandoah Valley Discovery Museum and Stonewall Jackson's Headquarters.

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 Shenandoah Valley Discovery Museum and Bright Box Theater while you're in the neighborhood.
Where is the best place to stay in Old Town Winchester?
Based on our traveler data, The George Washington Hotel, A Wyndham Grand Hotel is one of the top choices for your stay 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 13 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.