Find hotels in Old Town Winchester, Winchester from AED 245

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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, (1,005 reviews)
"The staff was helpful and kind. The architecture was incredible."
United States
Allison
The price is AED 449
AED 508 total
includes taxes & fees
25 May - 26 May
The George Washington Hotel, A Wyndham Grand Hotel

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
30.4 km from Old Town Winchester
7.6 out of 10, Good, (1,009 reviews)
"Location is right across the road from Spelunker's, the best casual restaurant in Virginia."
United States
Rachel
The price is AED 253
AED 282 total
includes taxes & fees
19 May - 20 May
Super 8 by Wyndham Front Royal Near Shenandoah National Park

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, (176 reviews)
"Everything about this special place is incredible."
United States
James
The price is AED 790
AED 871 total
includes taxes & fees
19 May - 20 May
L'Auberge Provencale Inn & Restaurant

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
2 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,021 reviews)
"Great location, clean rooms and friendly staff."
United States
Daniel
The price is AED 290
AED 328 total
includes taxes & fees
25 May - 26 May
Spark by Hilton Winchester

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, (280 reviews)
"Basic accommodations, clean room, friendly staff, decent continental breakfast options. Overall, a very nice stay for the price range. "
United States
Kevin
The price is AED 234
AED 265 total
includes taxes & fees
19 May - 20 May
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, (677 reviews)
"Wonderful staff, and fall cottage was lovely."
United States
Henrik
The price is AED 531
AED 687 total
includes taxes & fees
1 Jun - 2 Jun
Hillbrook Inn

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
25 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,012 reviews)
"I enjoyed my stay. The room was clean and the breakfast was varied."
United States
Brenda
The price is AED 450
AED 500 total
includes taxes & fees
31 May - 1 Jun
Hampton Inn Front Royal

Relax Inn Motel

Relax Inn Motel
2.0 star property
27.6 km from Old Town Winchester
8.2 out of 10, Very Good, (274 reviews)
"The owners/managers are delightful. The room was very nice with excellent bedding. I look forward to staying there again "
United States
Sarah
The price is AED 239
AED 266 total
includes taxes & fees
19 May - 20 May
Relax Inn Motel

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, (576 reviews)
"Very friendly staff in a great location and well maintained. Convenient shuttle to the casino. Staff was exceptionally friendly and helpful"
United States
Kevin
The price is AED 348
AED 427 total
includes taxes & fees
19 May - 20 May
The Inn at Charles Town - Hollywood Casino

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, (1,004 reviews)
"Best breakfast week had all week at a hotel. Friendly staff & clean rooms."
United States
Lauren
The price is AED 255
AED 288 total
includes taxes & fees
9 Jun - 10 Jun
Days Inn by Wyndham Charles Town/Harpers Ferry

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, (2,273 reviews)
"Friendly staff, clean spacious rooms, plenty of parking and a great breakfast. We enjoyed our stay here for sure!!"
United States
Natalie
The price is AED 426
AED 463 total
includes taxes & fees
20 May - 21 May
La Quinta Inn & Suites by Wyndham Winchester

Wayside Inn

Wayside Inn
3.5 star property
19.8 km from Old Town Winchester
9.2 out of 10, Wonderful, (433 reviews)
"The history surrounding this place is fascinating. It was such a charming historic inn."
United States
Bethany
The price is AED 446
AED 529 total
includes taxes & fees
19 May - 20 May
Wayside Inn

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, (1,100 reviews)
"Neat place and excellent stay"
United States
Anoop
The price is AED 387
AED 421 total
includes taxes & fees
9 Jun - 10 Jun
Comfort Inn & Suites Winchester

Motel 6 Front Royal, VA

Motel 6 Front Royal, VA
2.0 star property
27.7 km from Old Town Winchester
7.0 out of 10, Good, (515 reviews)
"No drinking water faucet ."
United States
Naveen
The price is AED 220
AED 245 total
includes taxes & fees
26 May - 27 May
Motel 6 Front Royal, VA

APM Inn & Suites

APM Inn & Suites
2.0 star property
2.3 km from Old Town Winchester
7.0 out of 10, Good, (437 reviews)
"Wonderful staff, very friendly & helpful… Room was clean, bed was comfortable & a good assortment of toiletries. They even provided coffee, bottled water & treats! Would stay again! "
United States
Brenda
The price is AED 234
AED 265 total
includes taxes & fees
21 May - 22 May
APM Inn & Suites

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, (447 reviews)
"Lovely inn with gracious hosts and fabulous breakfast. "
United States
Megan
The price is AED 557
AED 629 total
includes taxes & fees
1 Jun - 2 Jun
The Carriage Inn B&B

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
27.8 km from Old Town Winchester
8.2 out of 10, Very Good, (553 reviews)
"The room was very clean and comfortable. We enjoyed our stay and enjoyed being able to pull up to the room and unload with no steps or elevator to get on."
United States
Lawanda
The price is AED 309
AED 343 total
includes taxes & fees
19 May - 20 May
Twi-Lite 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, (501 reviews)
"Nice stay.. but the large mirror in front of the toilet freaked me out "
United States
Jennifer
The price is AED 415
AED 452 total
includes taxes & fees
19 May - 20 May
TownePlace Suites 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, (889 reviews)
"Location was excellent"
United States
Jennie
The price is AED 395
AED 447 total
includes taxes & fees
24 May - 25 May
Hampton Inn Winchester N/Conference Center, 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, (978 reviews)
"Beautiful hotel!"
United States
David
The price is AED 393
AED 428 total
includes taxes & fees
26 May - 27 May
Courtyard 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 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.
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 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.