The Courthouse in Winchester, Virginia.

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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, (1,004 reviews)
"Clean charming place to stay in the area "
United States
Elizabeth
$120 nightly
The price is $136
Jun 28 - Jun 29
Total with taxes and fees
The George Washington Hotel, A Wyndham Grand Hotel

2. Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
18.9 mi from Old Town Winchester
7.6 out of 10, Good, (1,001 reviews)
"room was clean and staff was friendly"
United States
Carol
$65 nightly
The price is $72
Jul 1 - Jul 2
Total with taxes and fees
Super 8 by Wyndham Front Royal Near Shenandoah National Park

3. Relax Inn Motel

Relax Inn Motel
2.0 star property
17.2 mi from Old Town Winchester
8.2 out of 10, Very Good, (281 reviews)
"The owners/managers are delightful. The room was very nice with excellent bedding. I look forward to staying there again "
United States
Sarah
$68 nightly
The price is $76
Jun 21 - Jun 22
Total with taxes and fees
Relax Inn Motel

4. Hillbrook Inn

Hillbrook Inn
4.0 star property
13.5 mi from Old Town Winchester
8.6 out of 10, Excellent, (679 reviews)
$158 nightly
The price is $174
Jun 23 - Jun 24
Total with taxes and fees
Hillbrook Inn

5. Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
2.5 star property
18.5 mi from Old Town Winchester
6.4 out of 10, (957 reviews)
"Convenient location to Skyline drive, and the caverns. 35 min from Lurray caverns. The room was clean, no issues. Breakfast was common and will get you through. Place was kept clean and staff was really nice."
United States
Craig
$59 nightly
The price is $65
Jul 1 - Jul 2
Total with taxes and fees
Baymont by Wyndham Front Royal Near Shenandoah National Park

6. Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
15.6 mi from Old Town Winchester
9.0 out of 10, Wonderful, (1,002 reviews)
"Clean , close to National park"
United States
Robert
$130 nightly
The price is $145
Jun 28 - Jun 29
Total with taxes and fees
Hampton Inn Front Royal

7. Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
1.3 mi from Old Town Winchester
9.0 out of 10, Wonderful, (1,007 reviews)
"Excellent hotel, very clean, nice beds."
United States
Sarat
$88 nightly
The price is $99
Jul 6 - Jul 7
Total with taxes and fees
Spark by Hilton Winchester

8. TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
2.7 mi from Old Town Winchester
9.2 out of 10, Wonderful, (971 reviews)
"Great hotel good location"
United States
Federico
$69 nightly
The price is $76
Jul 5 - Jul 6
Total with taxes and fees
TRU By Hilton Winchester

9. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
4.8 mi from Old Town Winchester
9.4 out of 10, Exceptional, (1,112 reviews)
"Decent accommodations, friendly staff."
United States
Juliet
$91 nightly
The price is $99
Jul 19 - Jul 20
Total with taxes and fees
Comfort Inn & Suites Winchester

10. Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
16 mi from Old Town Winchester
8.2 out of 10, Very Good, (1,005 reviews)
"Everything thing was good and there is a Mexican bar and restaurant attached to hotel."
United States
Ronald
$79 nightly
The price is $88
Jun 28 - Jun 29
Total with taxes and fees
Ramada by Wyndham Strasburg/Shenandoah Valley

11. L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
8.7 mi from Old Town Winchester
9.6 out of 10, Exceptional, (177 reviews)
"Everything about this special place is incredible."
United States
James
$244 nightly
The price is $269
Jun 24 - Jun 25
Total with taxes and fees
L'Auberge Provencale Inn & Restaurant

12. Wayside Inn

Wayside Inn
3.5 star property
12.3 mi from Old Town Winchester
9.2 out of 10, Wonderful, (438 reviews)
"Nice historic place"
United States
Donna
$131 nightly
The price is $144
Jun 29 - Jun 30
Total with taxes and fees
Wayside Inn

13. Travelodge By Wyndham Charles Town/Harpers Ferry

Travelodge By Wyndham Charles Town/Harpers Ferry
2.0 star property
18.3 mi from Old Town Winchester
7.2 out of 10, Good, (300 reviews)
"Everything was great"
United States
Maurice
$68 nightly
The price is $76
Jun 21 - Jun 22
Total with taxes and fees
Travelodge By Wyndham Charles Town/Harpers Ferry

14. La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
1.8 mi from Old Town Winchester
9.2 out of 10, Wonderful, (2,272 reviews)
"Breakfast was great and the staff were very nice!"
United States
Madeline
$114 nightly
The price is $124
Jun 24 - Jun 25
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester

15. Twi-Lite Inn

Twi-Lite Inn
2.0 star property
17.3 mi from Old Town Winchester
8.2 out of 10, Very Good, (559 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
$82 nightly
The price is $91
Jun 30 - Jul 1
Total with taxes and fees
Twi-Lite Inn

16. Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
1.3 mi from Old Town Winchester
9.2 out of 10, Wonderful, (903 reviews)
"The room was very clean and the front desk staffs were very nice."
United States
Angelina
$114 nightly
The price is $129
Jun 27 - Jun 28
Total with taxes and fees
Hampton Inn Winchester N/Conference Center, VA

17. Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
3.0 star property
15.5 mi from Old Town Winchester
9.0 out of 10, Wonderful, (1,000 reviews)
"It was a nice hotel for an over night stay. The room took a while to cool down but the overall stay was great."
United States
Joni
$113 nightly
The price is $126
Jul 1 - Jul 2
Total with taxes and fees
Fairfield Inn & Suites Strasburg Shenandoah Valley

18. Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
2.6 mi from Old Town Winchester
9.2 out of 10, Wonderful, (1,451 reviews)
"Excellent stay"
United States
Michael
$88 nightly
The price is $96
Jun 28 - Jun 29
Total with taxes and fees
Microtel Inn & Suites by Wyndham Winchester

19. Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
1.9 mi from Old Town Winchester
9.0 out of 10, Wonderful, (998 reviews)
"Clean room, pleasant staff."
United States
Kathrina
$101 nightly
The price is $110
Jun 28 - Jun 29
Total with taxes and fees
Courtyard by Marriott Winchester

20. Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry
2.0 star property
18.4 mi from Old Town Winchester
7.8 out of 10, Good, (1,003 reviews)
"Best breakfast week had all week at a hotel. Friendly staff & clean rooms."
United States
Lauren
$66 nightly
The price is $75
Jul 2 - Jul 3
Total with taxes and fees
Days Inn by Wyndham Charles Town/Harpers Ferry
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. Learn more about Old Town Winchester
Learn more about Old Town Winchester

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater.

Top Old Town Winchester Hotel Reviews

Find out more about Old Town Winchester

Top reasons to visit Old Town Winchester

  • Historic Architecture: Stroll through Old Town Winchester to admire its beautiful historical buildings and charming streets.
  • Vibrant Downtown: Enjoy shopping and dining at unique local shops and restaurants in the lively downtown area.
  • Outdoor Activities: Explore scenic parks and recreational areas perfect for leisurely walks or exciting adventures.
  • Family-Friendly Attractions: Discover engaging activities suitable for families, ensuring fun for all ages.
  • Varied Accommodations: Choose from a range of hotels, from historic inns to modern options, catering to diverse needs.

Find great hotels near Old Town Winchester

Explore a variety of hotel accommodations in Old Town Winchester, Virginia, where you'll find options ranging from charming historic inns to modern hotels. Whether you're traveling with pets, on a business trip, or seeking an LGBTQIA-friendly stay, Old Town Winchester has something for everyone. Enjoy the unique atmosphere and convenient amenities at hotels like Wyndham Winchester and various other local favorites that cater to your needs.

  • Travelodge by Wyndham Winchester: Experience comfort on a budget at Travelodge by Wyndham Winchester, a cozy motel with a guest rating of 8.6. Located 2 miles from Old Town Winchester, this property is ideal for travelers seeking a pet-friendly environment. With amenities such as waived fees for service animals and specific policies for pets, it’s a great choice for those traveling with furry companions. Guests appreciate its accessibility and welcoming atmosphere, making it a practical option for a relaxed getaway.
  • La Quinta Inn & Suites by Wyndham Winchester: Rated 9.2, La Quinta Inn & Suites by Wyndham Winchester blends affordability with modern conveniences. Situated 2 miles from Old Town Winchester, this hotel caters to both business and leisure travelers, offering a pet-friendly policy that permits dogs and cats. Amenities include in-room pet accommodations and waived fees for service animals, ensuring a comfortable stay. Guests rave about its clean rooms and attentive service, making it a top choice for those looking for quality and convenience.
  • Red Roof Inn Winchester, VA: A family-friendly option, Red Roof Inn Winchester, VA is a budget-friendly hotel located 2 miles from Old Town Winchester. It offers a welcoming atmosphere for families, featuring free cribs and amenities designed for children. With a guest rating that reflects its commitment to comfort, the hotel also allows pets, ensuring that no family member is left behind. Ideal for those traveling with kids and pets alike, this property combines convenience and warmth for an enjoyable stay.

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 historic Winchester district to admire its beautiful architecture, or explore the vibrant downtown area filled with friendly faces and local shops. Nearby, you can discover scenic parks and engaging family-friendly activities, making it an ideal destination for those seeking both adventure and a taste of local culture.

  • Winchester: Nestled in the picturesque Shenandoah Valley, Winchester offers visitors a delightful blend of outdoor adventure and rich history. The city is known for its scenic beauty, making it a popular destination for nature lovers and outdoor enthusiasts. Visitors can explore nearby national parks and lakes, participate in recreational activities, or simply enjoy the charming downtown area filled with shops and restaurants. With peak travel seasons in the summer and fall, Winchester invites tourists to experience its vibrant community and seasonal festivities.
  • Winchester Historic District: Just 0.2 miles from Old Town Winchester, the Winchester Historic District is a treasure trove of American history. This neighborhood features beautifully preserved buildings that date back to the 18th and 19th centuries, offering a glimpse into the past. Visitors can stroll through the district, enjoying outdoor activities and learning about the local heritage at various educational venues. The area is also close to national parks and a historic college university, providing plenty of opportunities for exploration and adventure.
  • College Park: Located 2 miles from Old Town Winchester, College Park is a vibrant village that caters to families and adventurers alike. With a welcoming atmosphere, this area boasts recreational spaces and shopping centers, making it a great spot for relaxation and fun. Visitors can enjoy the nearby national parks and parks that offer outdoor activities for all ages. College Park's family-friendly environment and access to various amenities make it a delightful addition to your travel itinerary.

Things to do near Old Town Winchester

Old Town Winchester offers a delightful mix of outdoor adventures and charming scenery, perfect for a vacation. Visitors can explore local attractions and enjoy the vibrant downtown area filled with unique shops and educational experiences. Don't miss the recreational areas that invite leisurely strolls or exciting activities, making it an ideal destination for tourists seeking both relaxation and adventure.

Shopping

In Old Town Winchester, visit the Old Town Mall for a variety of shops, including local boutiques and unique gift stores. Don't miss the Farmers Market on Loudoun Street for fresh produce and handmade crafts, perfect for souvenirs and gifts to take home.

Recreation

Sleepy Hollow Country Club offers a luxurious retreat just 21 miles from Old Town Winchester, featuring elegant facilities and a tranquil atmosphere. Enjoy golf, fine dining, and wellness amenities, all set against the backdrop of scenic landscapes, perfect for relaxation and rejuvenation.

Adventure

Explore the historic Old Town Winchester on a guided walking tour, where you'll uncover fascinating stories and architecture. For a thrill, try the escape rooms for a challenging adventure with friends, or enjoy a scenic bike ride along the 40-mile-long Winchester Green Circle Trail.

Nightlife

In Old Town Winchester, lively nightlife awaits at the vibrant Bright Box Theater, showcasing live music and comedy. Nearby, the Cork Street Tavern offers a cozy atmosphere with craft beers and delicious bites, perfect for unwinding after a day of exploring.

*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 options based on your budget, preferred location, and desired hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and eco-friendly accommodations currently available. To uncover the best prices and deals, simply sort the price filter from low to high.
  • 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 is perfect for outdoor and scenic vacations, offering a blend of historic houses, beautiful lakes, and significant historic places. This charming area caters to culture seekers and families alike. Don't miss the Old Town Winchester Walking Mall for shopping and dining, and consider local hotels for a comfortable stay while exploring this delightful destination.

  • Handley Regional Library: Nestled in the heart of Old Town Winchester, this library offers a welcoming atmosphere perfect for families. Explore its rich collection of books and resources while enjoying the cultural events and programs that engage the community.
  • Old Court House Civil War Museum: This museum, located in a historic courthouse, immerses visitors in the storied past of the Civil War. With exhibits that showcase artifacts and narratives, it provides a deep cultural insight into the region’s history and its significance during the war.
  • Patsy Cline Historic House: Just 0.4 miles from Old Town Winchester, this charming home celebrates the life of legendary country singer Patsy Cline. Experience her story through guided tours showcasing personal artifacts and memorabilia that highlight her remarkable career.

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 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

Traveling to Old Town Winchester is convenient via several major airports. Washington, DC (DCA-Ronald Reagan Washington National) is 65 miles away, with nearby hotels like the 5-star InterContinental Washington D.C. - The Wharf and Salamander Washington DC, both about 2 miles from the airport. Washington, DC (IAD-Washington Dulles Intl.) is 42 miles distant, offering options such as The Westin Washington Dulles Airport and Hyatt Regency, both 1 mile from the terminal. For those considering Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall), located 80 miles away, Pendry Baltimore and Four Seasons Hotel Baltimore are excellent CHOices, approximately 8 miles from the airport.

Frequently asked questions

What are the best hotels in Old Town Winchester that travelers recommend?
The George Washington Hotel, A Wyndham Grand Hotel is an excellent choice for travelers looking for highly recommended accommodations in Old Town Winchester.

This 3.5-star hotel, boasting an impressive 9.4 rating, is frequently praised by guests for its comfortable and clean rooms, as well as its friendly and helpful staff. Its great location places it conveniently near the Bright Box Theater and offers easy access to the Apple Valley Square Shopping Center. Guests also appreciate the free and easy parking, alongside modern and good amenities including an indoor pool and the option of premium bedding.
What are the best family hotels in Old Town Winchester?
For a highly-rated family-friendly 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 comfortable and clean rooms, with connecting room options and free cribs available for families. Guests consistently praise the friendly and helpful staff, as well as the hotel's great location. It provides modern amenities, including free internet and WiFi, and complimentary toiletries. Parking is also free and easy, adding to the convenience for families. The hotel is conveniently located near attractions like the Bright Box Theater, just 0.2 miles away.
What are the best spa hotels in Old Town Winchester?
For a top-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 onsite spa where guests can enjoy massage treatments daily. Travelers frequently praise its comfortable and clean rooms, as well as the helpful and friendly staff. Additional conveniences include free internet, complimentary toiletries, and free cribs upon request. Guests also appreciate the great location and the ease of free parking.
What are the best hotels in Old Town Winchester near Nalls Farm Market?
For a highly-rated hotel in Old Town Winchester near Nalls Farm Market, consider The George Washington Hotel, A Wyndham Grand Hotel.

This 3.5-star hotel boasts an impressive 9.4 rating and is conveniently located just one mile from Nalls Farm Market. Guests consistently praise its comfortable and clean rooms, as well as the friendly and helpful staff. The hotel offers modern amenities, including free internet and free WiFi, and provides free cribs and toiletries upon request, making it an excellent choice for families. Its great location also places it within easy reach of Bright Box Theater and Friendship Park.
When is the best time to go to Old Town Winchester?
While Old Town Winchester is lovely year-round, the best times to visit are during the spring and fall months.

Spring, from April to May, brings pleasant temperatures and the blooming of dogwoods, a hallmark of the Shenandoah Valley. This season is ideal for travelers who enjoy outdoor activities like strolling the pedestrian mall and visiting local orchards. The annual Shenandoah Apple Blossom Festival, a major event, also takes place in early May, offering parades, concerts, and various community celebrations.

Fall, from September to October, showcases the region's stunning foliage as the surrounding mountains transform into a canvas of red, orange, and gold. The cooler, crisp weather is great for exploring the historic streets and enjoying outdoor dining.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Old Town Winchester.
How can I save on a Old Town Winchester hotel booking with Expedia?
One Key™ - Expedia's free travel rewards program - gives you instant access to perks and Member Prices on Old Town Winchester hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings.

*OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Old Town Winchester hotel?
Prices for hotels in Old Town Winchester often vary, but you can find a great deal on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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