Hotels in Old Town Winchester, 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, (1,006 reviews)
"Location of hotel is great for walking to restaurants and shops. "
United States
Paul
The price is CA $179
CA $202 total
includes taxes & fees
May 13 - May 14
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, (1,002 reviews)
"Breakfast options were minimal."
United States
gregory
The price is CA $86
CA $96 total
includes taxes & fees
Apr 26 - Apr 27
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
25 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,000 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 CA $168
CA $187 total
includes taxes & fees
May 19 - May 20
Hampton Inn Front Royal

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, (963 reviews)
"Great location"
Canada
jim
The price is CA $146
CA $159 total
includes taxes & fees
Apr 30 - May 1
Courtyard by Marriott Winchester

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, (1,001 reviews)
"Very accessible to restaurants and stores"
United States
Scott
The price is CA $94
CA $106 total
includes taxes & fees
Apr 30 - May 1
Days Inn by Wyndham Charles Town/Harpers Ferry

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, (276 reviews)
"Decent continental breakfast. Night staff is friendly and helpful. Accessible. "
United States
David
The price is CA $87
CA $99 total
includes taxes & fees
Apr 20 - Apr 21
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 CA $200
CA $259 total
includes taxes & fees
Apr 21 - Apr 22
Hillbrook Inn

Relax Inn Motel

Relax Inn Motel
2.0 star property
27.6 km from Old Town Winchester
8.2 out of 10, Very good, (265 reviews)
"On my way back from shenendoah and Luray to dc place was fine "
United States
tara
The price is CA $85
CA $94 total
includes taxes & fees
Apr 20 - Apr 21
Relax Inn Motel

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, (1,105 reviews)
"Overall a pleasant stay!"
United States
Mark
The price is CA $149
CA $162 total
includes taxes & fees
May 11 - May 12
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 CA $99
CA $111 total
includes taxes & fees
Apr 22 - Apr 23
Rodeway Inn & Suites Charles Town

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
2 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,005 reviews)
"Nice staff, clean with a convenient location make it a good choice for a stay in Winchester. "
United States
Mira
The price is CA $120
CA $136 total
includes taxes & fees
Apr 26 - Apr 27
Spark by Hilton Winchester

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, (842 reviews)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is CA $127
CA $138 total
includes taxes & fees
Apr 27 - Apr 28
Fairfield Inn & 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, (878 reviews)
"The staff was wonderful! "
United States
Jayne
The price is CA $147
CA $167 total
includes taxes & fees
Apr 26 - Apr 27
Hampton Inn Winchester N/Conference Center, VA

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, (571 reviews)
"Clean room, friendly and helpful staff, good breakfast, I would stay again."
United States
Catherine
The price is CA $174
CA $195 total
includes taxes & fees
Apr 26 - Apr 27
TownePlace Suites by Marriott Front Royal

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, (560 reviews)
"Best place to stay if there for casino or a show."
United States
Kevin
The price is CA $137
CA $167 total
includes taxes & fees
May 10 - May 11
The Inn at Charles Town - Hollywood Casino

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 CA $150
CA $164 total
includes taxes & fees
Apr 22 - Apr 23
La Quinta Inn & Suites by Wyndham 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, (445 reviews)
"Lovely inn with gracious hosts and fabulous breakfast. "
United States
Megan
The price is CA $212
CA $240 total
includes taxes & fees
May 18 - May 19
The Carriage Inn B&B

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, (1,449 reviews)
"Everything,room was amazing, staff so friendly, breakfast very good "
United States
Douglas Gary
The price is CA $125
CA $136 total
includes taxes & fees
Apr 30 - May 1
Microtel Inn & Suites by Wyndham 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, (1,004 reviews)
"Very clean rooms and friendly staff."
United States
Christine
The price is CA $129
CA $141 total
includes taxes & fees
May 18 - May 19
Country Inn & Suites by Radisson, Winchester, VA

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, (1,002 reviews)
"Clean, staff was very polite and efficient."
United States
Marc
The price is CA $150
CA $165 total
includes taxes & fees
Apr 26 - Apr 27
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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

  • Scenic Walking Tours: Explore the charming streets of Old Town Winchester, rich in history and stunning architecture.
  • Vibrant Downtown: Enjoy a lively atmosphere with shops, restaurants, and cultural attractions like the Winchester Little Theatre.
  • Outdoor Adventures: Engage in various outdoor activities, including scenic lakes and parks ideal for family fun.
  • Wine Tastings: Indulge in local flavours with delightful wine tasting experiences in the area.
  • Diverse Accommodations: Find a range of comfortable stays, from pet-friendly hotels to cozy inns.

Find great hotels near Old Town Winchester

Experience the charm of Old Town Winchester with a variety of accommodation options that cater to every traveler's needs. From pet-friendly hotels to welcoming inns, you'll find comfortable stays perfect for both leisure and business trips. Discover popular choices like Wyndham Winchester and Quality Inn Winchester, ensuring a delightful visit to this historic area.

  • Travelodge by Wyndham Winchester: A budget-friendly option with a guest rating of 8.6, the Travelodge by Wyndham Winchester offers a cozy and welcoming atmosphere for travellers. Located 3.2km from Old Town Winchester, this motel is perfect for those seeking a pet-friendly experience. The property allows pets, with specific amenities such as waived fees for service animals and certain restrictions for pets. Guests can enjoy comfortable lodging and easy access to local attractions, making it an ideal choice for a relaxed getaway.
  • La Quinta Inn & Suites by Wyndham Winchester: Boasting a commendable guest rating of 9.2, La Quinta Inn & Suites is a superb choice for both business and leisure travellers. Situated 3.2km from Old Town Winchester, this hotel combines comfort with functionality. Known for its pet-friendly policy, it accommodates dogs and cats with specific restrictions and weight limits. Guests appreciate the modern amenities and the welcoming environment, ensuring a pleasant stay while being close to the vibrant attractions of Winchester.
  • Red Roof Inn Winchester, VA: Ideal for families and pet lovers alike, Red Roof Inn Winchester, VA offers a budget-friendly lodging experience just 3.2km from Old Town Winchester. This hotel provides amenities tailored for children, such as complimentary cribs, making it a great choice for families. With a flexible pet policy allowing dogs and cats, along with some restrictions, guests can enjoy a stress-free stay while making lasting memories in this charming town.

Where to stay near Old Town Winchester

Old Town Winchester invites you to explore its charming streets filled with rich history and friendly faces. Enjoy a family-friendly atmosphere while discovering top hotels and suites near the university for a perfect weekend getaway. Take in the scenic beauty of the area, where outdoor adventures await and the vibrant local culture enhances your travel experience. Don't miss the chance to immerse yourself in the unique vibes of this historic neighbourhood.

  • Winchester: Winchester is a charming city that showcases a perfect blend of outdoor adventures and scenic beauty. Nestled in the picturesque Shenandoah Valley, it offers a range of activities from recreational parks to thrilling ski options. The city attracts visitors year-round, with peak seasons in July to August and October, making it an ideal spot for both summer and autumn explorations. Notable attractions include the nearby national parks and serene lakes, providing ample opportunities for hiking, fishing, and enjoying nature's splendour.
  • Winchester Historic District: Located a mere 322m from Old Town Winchester, the Historic District is steeped in rich heritage and offers visitors a glimpse into the past. This neighborhood draws tourists seeking outdoor activities and scenic views, with peak visitor numbers matching those of Winchester. The area is home to several national parks and historic landmarks, as well as recreational spaces perfect for family outings. Enjoy a leisurely stroll through its charming streets, where history and adventure come together beautifully.
  • College Park: Just 3.2km from Old Town Winchester, College Park is a delightful village known for its family-friendly atmosphere and outdoor experiences. With a focus on adventure, this area features recreational areas and shopping centres, making it a great destination for families looking to unwind and explore. Like its neighbouring areas, College Park sees a consistent flow of visitors throughout the year, with peak periods in summer and fall. The proximity to national parks and local parks enhances the vibrant community spirit, inviting travellers to bask in nature's beauty.

Things to do near Old Town Winchester

Old Town Winchester, Virginia, is perfect for outdoor enthusiasts and adventure seekers. Visitors can enjoy scenic walking tours, indulge in wine tastings, explore downtown attractions, and discover nearby sites like the Wyndham Winchester. The area also boasts a variety of restaurants and a vibrant shopping centre, making it an ideal destination for relaxation and exploration.

Shopping

In Old Town Winchester, explore charming boutiques like The Vintage Shop for unique souvenirs and gifts. For a delightful local experience, visit the Old Town Farmers Market for fresh produce and artisanal goods, perfect for bringing home a taste of Virginia.

Recreation

Sleepy Hollow Country Club offers a luxurious escape just 33.8km from Old Town Winchester. Enjoy top-notch facilities, including golf, tennis, and a relaxing atmosphere perfect for unwinding. The stunning views and elegant surroundings create an ideal backdrop for rejuvenation and leisure.

Adventure

Explore the historic Old Town Winchester, where you can stroll along charming streets filled with boutiques and cafes. Experience the thrill of the Shenandoah Valley's outdoor activities, like hiking or biking on scenic trails, and enjoy local wineries for a taste of Virginia's finest wines.

Nightlife

In Old Town Winchester, explore vibrant pubs like the Loudoun Street Grill for craft beers and live music, or unwind at the vibrant Handley Library for unique events. Don't miss the charming atmosphere of local bars, where friendly locals and delicious cocktails create an inviting nightlife experience.

*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

  • 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 preferences, such as your budget, desired location, and preferred type of accommodation. To find the best prices and deals, simply 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 in and around Old Town Winchester

Old Town Winchester, Virginia, offers a delightful mix of outdoor adventures and cultural experiences, making it perfect for family vacations. Visitors can explore historic houses, scenic lakes, and charming historic sites. Don't miss the vibrant downtown Winchester, where you can find hotels, the Winchester Little Theatre, and the exciting Winchester Speedway. With a range of attractions catering to all interests, Old Town Winchester promises an unforgettable getaway.

  • Handley Regional Library: Immerse yourself in a cozy atmosphere at Handley Regional Library, where you can explore diverse collections and enjoy family-friendly events that celebrate community and culture.
  • Old Court House Civil War Museum: Step back in time at the Old Court House Civil War Museum, where you can delve into the rich history of the Civil War through engaging exhibits and artifacts, all set in a beautifully preserved historic building.
  • Patsy Cline Historic House: Just 644m away, visit the Patsy Cline Historic House, the childhood home of the legendary country singer. Experience her life and legacy through personal memorabilia and guided tours that highlight her impact on music.

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 SunnySlightly LowSlightly 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 SunnyAverageAverage

The nearest major airports for your trip to Old Town Winchester

Arriving in Old Town Winchester, Virginia, is convenient with several major airports nearby. Washington, DC (DCA-Ronald Reagan Washington National) is situated 104.6km away, with excellent hotels like the InterContinental Washington D.C. - The Wharf and Salamander Washington DC, both 3.2km from the airport. Alternatively, Washington, DC (IAD-Washington Dulles Intl.) is 67.6km away, featuring options such as The Westin Washington Dulles Airport and Hyatt Regency Dulles, both just 1.6km from the terminal. Lastly, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is 128.7km away, with luxury hotels like Pendry Baltimore and Four Seasons Hotel Baltimore, both located 12.9km from the airport.

Frequently asked questions

What are the best hotels in Old Town Winchester that travellers recommend?
For an excellent hotel in Old Town Winchester that travellers consistently recommend, consider The George Washington Hotel, A Wyndham Grand Hotel.

This 3.5-star hotel, with an outstanding 9.4 rating, is praised by guests for its comfortable and clean rooms, as well as its friendly and helpful staff. The hotel offers convenient amenities such as valet parking, an indoor pool, and accessible fitness facilities, some of which are available 24 hours a day or offer discounts at nearby locations. Its location is considered great, and guests appreciate the free and easy parking. The Bright Box Theater is just 0.3 km away, making it an ideal choice for those looking to enjoy local entertainment.
What are the best family hotels in Old Town Winchester?
For family-friendly accommodation in Old Town Winchester, The George Washington Hotel, A Wyndham Grand Hotel, is an excellent choice.

This 3.5-star hotel, with an impressive 9.4 rating, is highly regarded by families. Guests consistently mention the comfortable and clean rooms, along with the friendly and helpful staff. It offers free internet and WiFi, connecting rooms, and complimentary toiletries, which are all convenient for families. The hotel also provides free cribs upon request. Its location is considered great, and parking is free and easy. The George Washington Hotel is conveniently located near Bright Box Theater, just 0.3 km away, and Friendship Park is also within easy reach at 1.2 km.
What are the best spa hotels in Old Town Winchester?
For a highly-rated spa hotel in Old Town Winchester, The George Washington Hotel, A Wyndham Grand Hotel is an excellent choice.

This 3.5-star hotel, with an impressive 9.4 rating, offers a full-service spa with daily treatments and massage services, great for relaxation. Guests frequently praise the comfortable and clean rooms, the friendly and helpful staff, and the convenient location. Additionally, the hotel provides free internet and free WiFi, along with complimentary toiletries and free cribs upon request. Free and easy parking is also a welcome amenity.
When is the best time to go to Old Town Winchester?
The best time to go to Old Town Winchester is during the spring (April to May) or autumn (September to October) when the weather is pleasant and the town is particularly charming.

Spring brings blooming flowers and comfortable temperatures, great for strolling along the historic streets and enjoying outdoor dining. This is also when the famous Shenandoah Apple Blossom Festival takes place, usually in late April or early May, which fills the town with parades, music, and events. Couples often enjoy this time for its romantic feel and the chance to experience a lively local tradition.

Autumn offers crisp air and beautiful fall foliage, especially in late September and October. The cooler temperatures are ideal for exploring the walking mall and visiting nearby orchards for apple picking. Families will find this a lovely time to visit, with plenty of activities like pumpkin patches and corn mazes in the surrounding area, making for memorable day trips.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Old Town Winchester hotel for you.
How can I save on a Old Town Winchester hotel booking with Expedia?
With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Old Town Winchester hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings.
How much is the nightly rate at a Old Town Winchester hotel?
Hotel prices in Old Town Winchester often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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