Find Hotels with Connecting Rooms in Old Town Winchester, VA

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Check availability on Old Town Winchester Hotels with Connecting Rooms

Top Old Town Winchester Hotels with Connecting Rooms

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1012)
"Great hotel!"
United States
CHARLES
$127 nightly
The price is $143
Dec 16 - Dec 17
Total with taxes and fees
The George Washington Hotel, A Wyndham Grand Hotel

Microtel Inn & Suites by Wyndham Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (1374)
"Excellent accommodations"
United States
Loretta
$72 nightly
The price is $78
Jan 5 - Jan 6, 2026
Total with taxes and fees
Microtel Inn & Suites by Wyndham Winchester

Comfort Inn & Suites Winchester

2.5 star property
Winchester
9.4 out of 10, Exceptional, (1075)
"Very clean, helpful staff"
United States
Kathleen
$100 nightly
The price is $109
Jan 5 - Jan 6, 2026
Total with taxes and fees
Comfort Inn & Suites Winchester

TRU By Hilton Winchester

2.5 star property
Winchester
9.0 out of 10, Wonderful, (765)
"The hotel was clean and the staff was pleasant."
United States
Sherri
$73 nightly
The price is $79
Jan 7 - Jan 8, 2026
Total with taxes and fees
TRU By Hilton Winchester

Rodeway Inn & Suites - Charles Town, WV

2.0 star property
Charles Town
8.6 out of 10, Excellent, (1002)
"Good for me and front desk allowed me to check in early"
United States
Devan
$64 nightly
The price is $72
Dec 28 - Dec 29
Total with taxes and fees
Rodeway Inn & Suites - Charles Town, WV

The Carriage Inn B&B

3.5 star property
Charles Town
9.6 out of 10, Exceptional, (439)
"Excellent accommodations and breakfast. "
United States
William
$127 nightly
The price is $144
Dec 15 - Dec 16
Total with taxes and fees
The Carriage Inn B&B

La Quinta Inn & Suites by Wyndham Winchester

3.0 star property
Winchester
9.2 out of 10, Wonderful, (2221)
"Clean, beautiful bedding Friendly staff"
United States
Heather
$105 nightly
The price is $115
Dec 16 - Dec 17
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester

SpringHill Suites by Marriott Winchester

2.5 star property
Winchester
9.4 out of 10, Exceptional, (774)
"Clean room, courteous and professional staff. Great breakfast selections"
United States
Lauris
$107 nightly
The price is $117
Dec 14 - Dec 15
Total with taxes and fees
SpringHill Suites by Marriott Winchester

Spark by Hilton Winchester

3.0 star property
Winchester
9.0 out of 10, Wonderful, (1001)
"Great location close to restaurants "
United States
SILVIA
$75 nightly
The price is $85
Jan 4 - Jan 5, 2026
Total with taxes and fees
Spark by Hilton Winchester

Country Inn & Suites by Radisson, Winchester, VA

3.0 star property
Winchester
8.8 out of 10, Excellent, (1006)
"Have stayed here multiple times -always good"
United States
Robert
$85 nightly
The price is $93
Jan 4 - Jan 5, 2026
Total with taxes and fees
Country Inn & Suites by Radisson, Winchester, VA
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.

Find out more about Old Town Winchester

Discover top Old Town Winchester attractions

Old Town Winchester offers travelers a delightful blend of history, culture, and charm. Start your exploration at the historic Old Court House, which showcases stunning architecture and engaging exhibits that narrate the region's rich past. Just a short stroll away, the Museum of the Shenandoah Valley captivates visitors with its art collections and beautifully landscaped gardens, perfect for a family picnic or a leisurely afternoon. Don't miss the vibrant Winchester Farmers Market, where you can sample local produce and artisan goods, providing a taste of the area's agricultural heritage. For those seeking a thrill, the nearby Shenandoah Valley Discovery Museum offers interactive exhibits that are both educational and entertaining, making it a hit with kids and adults alike. Lastly, immerse yourself in the local food scene with a visit to one of the many farm-to-table restaurants, where seasonal ingredients shine in every dish. Staying in one of the boutique hotels in Old Town Winchester enhances the travel experience, as many accommodations are housed in charming historic buildings that blend modern comforts with classic aesthetics. Expect personalized service, with staff eager to share insider tips about hidden gems in the neighborhood. Many hotels feature unique amenities like complimentary breakfasts made with local ingredients, cozy lounges for evening relaxation, and nearby local attractions, ensuring that every moment of your stay is enjoyable and convenient. Whether you're unwinding after a day of discovery or gearing up for new adventures, Old Town Winchester's accommodations promise a memorable experience tailored to your family's needs.

Find the best hotels with connecting rooms in Old Town Winchester

Families and groups looking to stay together in Old Town Winchester will appreciate these top hotels that offer connecting rooms for a more comfortable experience. Each option provides a unique blend of amenities to cater to your needs.

The George Washington Hotel, A Wyndham Grand Hotel

  • Why it's great for extra space: Ideal for families or groups, The George Washington Hotel provides an exceptional stay with its connecting rooms, making it easy for guests to stay close. Rated highly with a review score of 9.4, this hotel features spacious rooms that ensure comfort and convenience for all travelers. Guests can also enjoy a range of amenities including a relaxing indoor pool and a full-service spa, perfect for unwinding after a busy day of exploring Old Town Winchester.
  • Other amenities: In addition to connecting rooms, the hotel offers a variety of features to enhance your stay. Guests can take advantage of free internet access, valet parking, and a 24-hour fitness center. Start your day with a complimentary breakfast for children, and enjoy daily housekeeping services. For those looking to explore, nearby activities include skiing, golfing, mountain biking, and hiking. Whether you're here for leisure or adventure, The George Washington Hotel caters to all your needs.
  • Neighborhood: Old Town Winchester
  • Nearby attractions: Handley Regional Library - 0.25 miles, Bright Box Theater - 0.22 miles, Old Court House Civil War Museum - 0.22 miles

Top Old Town Winchester Hotel Reviews

Frequently asked questions

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