Find hotels in Old Town Winchester, Winchester from AED 265

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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 AED 465
AED 527 total
includes taxes & fees
22 Dec - 23 Dec
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, (770)
"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is AED 262
AED 285 total
includes taxes & fees
5 Jan - 6 January 2026
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 AED 363
AED 395 total
includes taxes & fees
12 Jan - 13 January 2026
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 AED 477
AED 571 total
includes taxes & fees
30 Dec - 31 Dec
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 AED 561
AED 720 total
includes taxes & fees
5 Jan - 6 January 2026
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 AED 242
AED 273 total
includes taxes & fees
21 Dec - 22 Dec
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, (1007)
"Certainly will stay again "
United States
philip
The price is AED 234
AED 265 total
includes taxes & fees
4 Jan - 5 January 2026
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, (1381)
"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 AED 273
AED 297 total
includes taxes & fees
31 Dec - 1 January 2026
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 AED 377
AED 410 total
includes taxes & fees
4 Jan - 5 January 2026
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 AED 276
AED 313 total
includes taxes & fees
4 Jan - 5 January 2026
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, (1004)
"Have stayed here multiple times -always good"
United States
Robert
The price is AED 308
AED 335 total
includes taxes & fees
11 Jan - 12 January 2026
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 AED 257
AED 291 total
includes taxes & fees
24 Dec - 25 Dec
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 AED 394
AED 438 total
includes taxes & fees
22 Dec - 23 Dec
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, (782)
"The staff were friendly and knowledgeable . Clean room and breakfast was excellent. Hotel close to restaurants and stores. "
United States
Yolanda
The price is AED 393
AED 428 total
includes taxes & fees
21 Dec - 22 Dec
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 AED 443
AED 500 total
includes taxes & fees
30 Dec - 31 Dec
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 AED 286
AED 312 total
includes taxes & fees
3 Jan - 4 January 2026
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 AED 358
AED 395 total
includes taxes & fees
22 Dec - 23 Dec
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 AED 278
AED 302 total
includes taxes & fees
4 Jan - 5 January 2026
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 AED 393
AED 428 total
includes taxes & fees
22 Dec - 23 Dec
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, (798)
"Quick check in, clean room, friendly staff."
United States
Darcy
The price is AED 340
AED 370 total
includes taxes & fees
18 Dec - 19 Dec
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 of Old Town Winchester, filled with historic landmarks and local shops.
  • Outdoor Adventures: Enjoy scenic views and outdoor activities, perfect for families and nature enthusiasts.
  • Walking Tours: Immerse yourself in the rich history with guided walking tours of the area.
  • Vibrant Atmosphere: Experience a friendly and lively neighborhood, bustling with culture and charm.
  • Diverse Accommodations: Choose from a variety of lodging options, including historic hotels and pet-friendly stays.

Find great hotels near Old Town Winchester

Old Town Winchester offers a variety of lodging options to suit every traveler's needs, from pet-friendly hotels to historic accommodations. Whether you're seeking a Wyndham hotel close to the heart of the town or a unique agritourism experience, you'll find welcoming places perfect for business travelers and LGBTQIA guests alike. Enjoy a memorable stay in this charming destination, where comfort and convenience meet.

  • Travelodge by Wyndham Winchester: Embrace a comfortable and budget-friendly stay at Travelodge by Wyndham Winchester, located a mere 3.2km from the historic charm of Old Town Winchester. This motel-style lodging is perfect for travelers seeking a pet-friendly experience, welcoming pets with open arms. With amenities designed for convenience, such as complimentary Wi-Fi and on-site parking, guests can enjoy a hassle-free stay. The property’s pet policy ensures a warm embrace for your furry companions, offering a unique, family-friendly atmosphere that makes it an excellent choice for pet owners.
  • La Quinta Inn & Suites by Wyndham Winchester: Experience a blend of comfort and inclusivity at La Quinta Inn & Suites by Wyndham Winchester, just 3.2km from the heart of Old Town. This hotel caters to a diverse range of travelers, including LGBTQIA guests, and provides a welcoming environment for all. Business travelers will appreciate the modern amenities, including free Wi-Fi and a business center, while pet owners can bring their dogs and cats along, thanks to the hotel’s pet-friendly policies. Guests rave about the spacious rooms and complimentary breakfast that sets the tone for a positive start to the day.
  • Red Roof Inn Winchester, VA: Discover a family-friendly atmosphere at Red Roof Inn Winchester, VA, located 3.2km from Old Town Winchester. This hotel strikes a perfect balance between comfort and affordability, making it an ideal choice for families, LGBTQIA travelers, and pet owners alike. With amenities for children, including complimentary cribs, the hotel ensures a welcoming environment for guests of all ages. Pets are also warmly accepted, making it easy to include your furry friends in your vacation plans. Enjoy convenient access to local attractions while relaxing in well-appointed rooms that prioritize guest comfort.

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 and historic landmarks, all within walking distance. Experience the friendly atmosphere and scenic views as you explore this vibrant neighborhood. Nearby, you'll find additional attractions that enhance your vacation with a unique mix of urban and historical vibes.

  • Winchester: Nestled in the picturesque Shenandoah Valley, Winchester is a vibrant city that serves as the heart of the region. With its rich history and charming architecture, Old Town Winchester invites visitors to explore its quaint shops and eateries. Outdoor enthusiasts can enjoy nearby national parks and recreational areas, perfect for hiking, biking, and scenic views. The peak travel months from July to August and October highlight the city’s appeal for adventure seekers, while winter months offer a quieter experience. Don’t miss the chance to visit local landmarks like the serene lake and state parks that enhance the area's natural beauty.
  • Winchester Historic District: Located a mere 322m from Old Town Winchester, this charming neighborhood is steeped in history and offers a delightful glimpse into the past. Visitors can stroll along cobblestone streets lined with historic buildings and museums. The area is perfect for outdoor enthusiasts, with access to recreational areas and golf courses. Similar to Winchester, peak visitor numbers occur in July to August and October, making it a bustling destination for those seeking adventure and scenery. The nearby national parks and historic colleges add to the allure, creating a unique blend of education and exploration.
  • Stephens City: Just 11.3km from Old Town Winchester, Stephens City is a quaint town that boasts a friendly atmosphere and numerous outdoor activities. Known for its recreational areas and entertainment facilities, visitors can enjoy everything from arcade adventures to local events. The town's visitor numbers peak in April and June to July, offering a lively ambiance during the warmer months. With proximity to national parks, state parks, and a lovely lake, Stephens City is an excellent choice for those looking to immerse themselves in nature while enjoying small-town charm.

Things to do in and around Old Town Winchester

Discover the charm of Old Town Winchester, Virginia, where outdoor adventures and scenic views await. Enjoy shopping at local malls and recreational areas, and immerse yourself in history with walking tours and a detailed travel itinerary of historic sites. Whether you're exploring the vibrant atmosphere or seeking activities in Winchester, there's something for every traveler to enjoy.

Shopping

Nalls Farm Market, located 1.6km from Old Town Winchester, offers a delightful selection of fresh produce and unique souvenirs. Nearby, Apple Valley Square Shopping Center and Northside Station Shopping Center, both 1.6km away, feature a variety of shops that cater to family and business needs, enhancing your shopping experience.

Recreation

Experience the serene atmosphere at Jim Barnett Park, where you can unwind amidst nature and enjoy leisurely strolls. For golf enthusiasts, Rock Harbor Golf Course offers a scenic outdoor experience just 3.2km away, while Appleland Sports Center invites you to engage in various recreational activities 9.7km from Old Town Winchester.

Adventure

Experience the thrill of motorsports at Summit Point Motorsports Park, located 17.7km from Old Town Winchester, where adrenaline meets speed. For a family-friendly adventure, visit Watermelon Park Campground, 20.9km away, offering outdoor fun and relaxation. Hike scenic trails at Tuckers Lane Trailhead, 32.2km from town.

Nightlife

Experience the vibrant nightlife in Old Town Winchester with a visit to Bright Box Theater for romance and entertainment. For a family-friendly outing, check out the Morgan County Observatory, located 33.8km away. Don't miss the Winchester Little Theater, just 483m away, for more cultural vibes.

*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 on your trip to Old Town Winchester, consider visiting between January and March for lower hotel rates, especially on Tuesdays. Avoid Saturdays, which are the priciest days. Use Expedia to filter for budget-friendly, eco-certified hotels and sort by price for the best deals. Look for package options that combine flights, accommodations, and activities for added savings. Additionally, explore free local attractions and take advantage of public transport to navigate the area affordably. Keep an eye out for last-minute deals and discounts on beverages while you enjoy your stay.

  • 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 refine 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.

Find the best attractions in and around Old Town Winchester

Old Town Winchester offers a delightful blend of outdoor adventures and rich history, perfect for family experiences. Visitors can explore the historic district, stroll through the charming old town walking mall, and visit nearby museums. The area is known for its scenic lakes and historic houses, making it an ideal destination for those seeking culture and adventure.

  • Shenandoah University: Located one mile from Old Town Winchester, Shenandoah University offers a blend of historic charm and vibrant campus life. Explore the beautiful grounds and enjoy the cultural events that frequently take place, showcasing local talent and academic achievements.
  • Museum of the Shenandoah Valley: Just 1.3km away, this art museum features an impressive collection of regional artworks and artifacts. Visitors can immerse themselves in the rich cultural history of the Shenandoah Valley through engaging exhibits and serene gardens.
  • Shenandoah Valley Discovery Museum: Situated within Old Town Winchester, this children's museum is a fantastic place for families. With interactive exhibits, it encourages learning through play, making it an enriching experience for young visitors.

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

Visitors to Old Town Winchester can conveniently fly into several nearby airports. Washington Dulles International Airport (IAD) is 67.6km away, with excellent hotel options like the 4-star Hyatt Regency Dulles, located 1.6km from the airport. Martinsburg, WV, Eastern West Virginia Regional Airport (MRB) is only 29.0km away, with accommodations such as the Hillbrook Inn, a charming 4-star bed & breakfast, 11.6kms from the airport. For those considering Hagerstown Regional Airport (HGR), located 69.2km away, The Mercersburg Inn, a 4-star inn, is 19.3km from the airport, offering a cozy stay. Transportation services are readily accessible from each hotel to their respective airports.

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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.