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Find hotels in Old Town Winchester, Winchester from NT$2,153

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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, (1010)
"Great hotel!"
United States
CHARLES
The price is NT$3,951
NT$4,476 total
includes taxes & fees
Dec 21 - Dec 22
The George Washington Hotel, A Wyndham Grand Hotel

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
4.4 km from Old Town Winchester
9.0 out of 10, Wonderful, (767)
"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is NT$2,221
NT$2,416 total
includes taxes & fees
Jan 5 - 2026/1/6
TRU By Hilton 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, (1077)
"Very clean, helpful staff"
United States
Kathleen
The price is NT$3,085
NT$3,357 total
includes taxes & fees
Jan 12 - 2026/1/13
Comfort Inn & Suites Winchester

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, (523)
"Friendly staff, comfortable bed, convenient location "
United States
Kourtney
The price is NT$4,055
NT$4,853 total
includes taxes & fees
Dec 30 - Dec 31
The Inn at Charles Town - Hollywood Casino

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 NT$4,960
NT$6,335 total
includes taxes & fees
Dec 16 - Dec 17
Hillbrook 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, (1003)
"The room is clean. The staff is friendly. The breakfast was good. No-frills hotel, but clean and efficient. "
United States
Kelsey
The price is NT$2,054
NT$2,322 total
includes taxes & fees
Dec 21 - Dec 22
Days Inn by Wyndham Charles Town/Harpers Ferry

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, (1006)
"Certainly will stay again "
United States
philip
The price is NT$1,988
NT$2,247 total
includes taxes & fees
Dec 28 - Dec 29
Rodeway Inn & Suites Charles Town

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, (1380)
"Clean nice room with a hot breakfast, a lot nicer then other places in Winchester especially for the price. Highly recommend "
United States
Curtis
The price is NT$2,321
NT$2,525 total
includes taxes & fees
Dec 31 - 2026/1/1
Microtel Inn & Suites by Wyndham Winchester

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, (2226)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is NT$3,171
NT$3,450 total
includes taxes & fees
Jan 12 - 2026/1/13
La Quinta Inn & Suites by Wyndham Winchester

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
2 km from Old Town Winchester
9.0 out of 10, Wonderful, (1003)
"Great location close to restaurants "
United States
SILVIA
The price is NT$2,346
NT$2,658 total
includes taxes & fees
Jan 4 - 2026/1/5
Spark by Hilton Winchester

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, (1003)
"Have stayed here multiple times -always good"
United States
Robert
The price is NT$2,612
NT$2,841 total
includes taxes & fees
Jan 4 - 2026/1/5
Country Inn & Suites by Radisson, Winchester, VA

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, (1005)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is NT$2,184
NT$2,469 total
includes taxes & fees
Dec 23 - Dec 24
Holiday Inn Winchester Se-Historic Gateway by IHG

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
25 km from Old Town Winchester
9.0 out of 10, Wonderful, (1002)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is NT$3,344
NT$3,722 total
includes taxes & fees
Dec 21 - Dec 22
Hampton Inn Front Royal

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, (780)
"The staff were friendly and knowledgeable . Clean room and breakfast was excellent. Hotel close to restaurants and stores. "
United States
Yolanda
The price is NT$3,341
NT$3,635 total
includes taxes & fees
Dec 21 - Dec 22
SpringHill Suites by Marriott Winchester

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, (439)
"Excellent accommodations and breakfast. "
United States
William
The price is NT$4,043
NT$4,569 total
includes taxes & fees
Dec 29 - Dec 30
The Carriage Inn B&B

Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG
2.5 star property
3.1 km from Old Town Winchester
8.8 out of 10, Excellent, (544)
"Very clean room, excellent staff!!!"
United States
James
The price is NT$2,433
NT$2,647 total
includes taxes & fees
Jan 3 - 2026/1/4
Candlewood Suites Winchester by IHG

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, (1003)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is NT$3,044
NT$3,357 total
includes taxes & fees
Dec 21 - Dec 22
DoubleTree by Hilton Front Royal Blue Ridge Shadows

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
4.3 km from Old Town Winchester
9.2 out of 10, Wonderful, (1003)
"Great stay"
United States
Jaron
The price is NT$2,360
NT$2,568 total
includes taxes & fees
Jan 4 - 2026/1/5
Quality Inn 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, (915)
"comfortable room, amenities and staff"
United States
Prashant
The price is NT$3,338
NT$3,631 total
includes taxes & fees
Dec 21 - Dec 22
Courtyard by Marriott 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, (797)
"Quick check in, clean room, friendly staff."
United States
Darcy
The price is NT$2,890
NT$3,144 total
includes taxes & fees
Dec 17 - Dec 18
Fairfield Inn & Suites by Marriott 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 District: Explore the charming streets filled with historic houses and museums that showcase Winchester's rich heritage.
  • Outdoor Adventures: Enjoy scenic views and recreational activities at nearby lakes and parks, perfect for families and outdoor enthusiasts.
  • Vibrant Downtown: Stroll through the lively downtown area, featuring local shops, cafes, and a friendly atmosphere.
  • Walking Tours: Participate in guided walking tours to uncover the captivating stories behind Old Town's historic landmarks.
  • Diverse Accommodations: Choose from a variety of lodging options, blending historic charm with modern comfort.

Find great hotels near Old Town Winchester

Explore a range of hotel accommodations in Old Town Winchester, Virginia, where historic charm meets modern comfort. From pet-friendly options to LGBTQIA welcoming environments, you'll find a variety of lodging types, including the renowned Wyndham Winchester. Whether you're seeking a cozy hotel near the vibrant heart of Old Town or a unique agritourism property, your perfect getaway awaits in this captivating destination.

  • Travelodge by Wyndham Winchester: Nestled a mere 3.2km from Old Town Winchester, Travelodge by Wyndham Winchester provides a cozy, pet-friendly lodging experience. This motel is perfect for travelers seeking comfort without sacrificing companionship, as it welcomes pets with open arms. Guests can enjoy a range of amenities, including a transparent pet policy that allows for service animals and some pets on-site. With its relaxed atmosphere and accessibility, this property caters to those looking for a straightforward, enjoyable stay while exploring the charming historic district of Winchester.
  • La Quinta Inn & Suites by Wyndham Winchester: A modern hotel located 3.2km from Old Town Winchester, La Quinta Inn & Suites is ideal for both business and leisure travelers. This welcoming property is LGBTQIA-friendly and pet-friendly, making it a great choice for diverse guests. With amenities that include in-room pet accommodations and a supportive environment for LGBTQIA travelers, La Quinta ensures everyone feels at home. The hotel’s convenient location and comfortable rooms make it a fantastic base for exploring the vibrant culture and history of Winchester.
  • Red Roof Inn Winchester, VA: Positioned just 3.2km from Old Town Winchester, Red Roof Inn is a family-oriented hotel that offers a welcoming space for everyone, including pets. This LGBTQIA-friendly establishment provides special amenities for children, such as free cribs, making it a perfect choice for families. Guests can enjoy the comfort of pet-friendly rooms and a commitment to inclusivity. With its prime location and family-focused services, Red Roof Inn is an excellent option for those looking to explore the area while enjoying a warm, accommodating environment.

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 the picturesque streets lined with local shops, cafes, and historical sites, all within walking distance. You'll experience the friendly atmosphere and scenic beauty of this vibrant neighborhood, making it an ideal base for exploring nearby attractions and immersing yourself in the rich culture of Winchester.

  • Winchester: Winchester is a charming city that serves as the heart of the region, with Old Town Winchester nestled within its vibrant streets. Known for its outdoor adventures and picturesque scenery, visitors flock to Winchester year-round, with peak seasons during the summer and fall. Popular activities include hiking in nearby national parks, exploring local lakes, and enjoying the area's rich history. The city boasts a variety of recreational areas and educational venues, making it perfect for nature lovers and history buffs alike.
  • Winchester Historic District: Located just 322m from Old Town Winchester, the Winchester Historic District is a beautifully preserved neighborhood that takes you back in time. Here, outdoor enthusiasts can enjoy the abundant recreational spaces while soaking in the area's historical significance. With golf courses and educational venues nearby, this district offers a perfect mix of adventure and relaxation. The historic college university and national parks in close proximity add to the allure, making it an ideal spot for travelers seeking a scenic and educational experience.
  • College Park: Situated 3.2km away from Old Town Winchester, College Park is a delightful village known for its vibrant community and outdoor activities. Visitors can explore recreational areas, shopping centers, and various shopping districts, making it a perfect destination for both leisure and retail therapy. College Park also benefits from its closeness to national parks and visitor centers, allowing for easy access to nature and local attractions. The area's charm and accessibility make it a great addition to your Winchester exploration.

Things to do in and around Old Town Winchester

Old Town Winchester offers a delightful blend of outdoor adventures and scenic views, perfect for a vacation. Visitors can enjoy shopping at local centers, explore historic sites with detailed travel itineraries, and participate in walking tours to discover the area's rich heritage. Don't miss the chance to experience the vibrant recreational areas that make Old Town Winchester a charming destination.

Shopping

For a delightful shopping experience in Old Town Winchester, visit Nalls Farm Market for fresh local produce and unique gifts. Apple Valley Square Shopping Center and Northside Station Shopping Center both offer a variety of shops with a friendly atmosphere, perfect for finding souvenirs and enjoying the local vibe.

Recreation

At Rock Harbor Golf Course, enjoy a round of golf surrounded by scenic landscapes, perfect for relaxation and outdoor activity. Jim Barnett Park, a short walk away, offers serene walking trails and picnic spots for wellness. Appleland Sports Center, a bit further out, features recreational facilities promoting health and fitness.

Adventure

Experience thrilling motor racing at Summit Point Motorsports Park, located 17.7km from Old Town Winchester. For a family-friendly outdoor adventure, visit Watermelon Park Campground, 20.9km away. Explore scenic trails at Tuckers Lane Trailhead, situated 32.2km from town, perfect for hiking enthusiasts seeking adventure.

Nightlife

In Old Town Winchester, Bright Box Theater offers a vibrant mix of romance and culture, perfect for an entertaining night out. Nearby, Winchester Little Theater provides an intimate atmosphere for theatrical performances. For a unique experience, head to Morgan County Observatory for family-friendly stargazing just 33.8km away.

*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

To save money during your visit to Old Town Winchester, consider traveling between January and March for lower accommodation rates, especially on Tuesdays, as Saturdays tend to be pricier. Use Expedia's search tool to find budget-friendly options, filtering for Eco-certified hotels and sorting by price. Look for package deals that combine flights, hotels, and activities for additional savings. Don't miss out on free activities like exploring the historic district and local parks. Always check for last-minute deals and beverage discounts to maximize your budget.

  • 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: Utilize Expedia’s search tool to tailor your options based on your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To find the best prices and deals, simply sort 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 deal.

Find the best attractions in and around Old Town Winchester

Old Town Winchester offers a delightful mix of outdoor adventures and rich history, perfect for family experiences. Visitors can explore the historic district, including charming historic houses and museums. Don't miss the scenic lake nearby for relaxation, and take a stroll through the vibrant historic downtown to fully appreciate the area's culture and heritage. Discover the unique attractions that make Old Town Winchester a must-visit destination.

  • Shenandoah University: Located 1.6km from Old Town Winchester, this historic university offers a blend of academic excellence and cultural vibes. Stroll the picturesque campus, enjoy beautiful architecture, and immerse yourself in the dynamic student atmosphere.
  • Museum of the Shenandoah Valley: Just 1.3km away, this art museum showcases regional history and fine art. Explore its diverse collections, beautiful gardens, and engaging exhibitions that highlight the cultural significance of the Shenandoah Valley.
  • Shenandoah Valley Discovery Museum: Situated within Old Town Winchester, this children's museum provides interactive exhibits that engage families. It's a fun place for kids to learn through play, fostering creativity and curiosity in a vibrant cultural setting.

Best time to go to Old Town Winchester

The best time to visit Old Town Winchester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Old Town Winchester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature around Old Town Winchester falls in January, 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

Traveling to Old Town Winchester, Virginia, is convenient with several nearby airports. Washington Dulles International Airport (IAD) is located 67.6km away, with great hotel options like the 4-star Hyatt Regency Dulles and The Westin Washington Dulles Airport, both just 1.6km from the airport. Martinsburg, WV, houses Eastern West Virginia Regional Airport (MRB), situated 29.0km away, with nearby accommodations such as the Hillbrook Inn and the Carriage Inn B&B, both 11.6kms distant. For those considering Hagerstown Regional Airport (HGR), located 69.2km away, options include the 4-star Mercersburg Inn and Courtyard Marriott Hagerstown, just 9.7km from the airport.

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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.
Where can I learn more about changing or cancelling my trip to Old Town Winchester?
For additional details about rescheduling or cancelling your trip to Old Town Winchester, head over to our customer service page.
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.