Find Hotels with Connecting Rooms in Winchester, VA

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Check availability on Winchester Hotels with Connecting Rooms

Check prices for these dates

Tonight
Jul 14 - Jul 15
Tomorrow
Jul 15 - Jul 16
This weekend
Jul 18 - Jul 20
Next weekend
Jul 25 - Jul 27

Top Winchester Hotels with Connecting Rooms

Spark by Hilton Winchester
Relax in the stylish lobby with a seating area, mezzanine level, and comfortable bench.

Spark by Hilton Winchester

3.0 star property
9.0 out of 10, Wonderful, (1004)
"Great stay. Very friendly staff and the room was clean and comfortable. "
$92 nightly
The price is $104
Jul 27 - Jul 28
Total includes taxes and fees
Spark by Hilton Winchester
Quality Inn
Guests can enjoy a covered outdoor seating area with beautiful landscaping and a paved pathway to the entrance.

Quality Inn

2.5 star property
9.2 out of 10, Wonderful, (1004)
"Very nice lodging and breakfast. Would stay here again."
$93 nightly
The price is $101
Jul 21 - Jul 22
Total includes taxes and fees
Quality Inn
Country Inn & Suites by Radisson, Winchester, VA
Cozy living room with a fireplace, wooden shelves, and a light-colored sofa.

Country Inn & Suites by Radisson, Winchester, VA

3.0 star property
8.8 out of 10, Excellent, (1005)
"Great stay for a great price!"
$97 nightly
The price is $105
Jul 20 - Jul 21
Total includes taxes and fees
Country Inn & Suites by Radisson, Winchester, VA
Hampton Inn Front Royal
Classic hotel exterior with a symmetrical facade, large windows, and a prominent entrance.

Hampton Inn Front Royal

2.5 star property
9.0 out of 10, Wonderful, (1006)
"The quick breakfast was perfect."
$110 nightly
The price is $122
Aug 14 - Aug 15
Total includes taxes and fees
Hampton Inn Front Royal
Hampton Inn Winchester-University/Mall Area
Welcome to Hampton Inn, featuring a symmetrical design with a flat roof and large windows.

Hampton Inn Winchester-University/Mall Area

2.5 star property
9.0 out of 10, Wonderful, (1003)
"Clean, friendly, comfortable bed and decent hot breakfast & fresh fruit. "
$99 nightly
The price is $113
Jul 27 - Jul 28
Total includes taxes and fees
Hampton Inn Winchester-University/Mall Area
Hilton Garden Inn Winchester
Relax by the pool in a spacious area with multiple seating options and a clear view of the surroundings.

Hilton Garden Inn Winchester

3.0 star property
8.8 out of 10, Excellent, (481)
"Is perfect , clean and comfortable. Great location. "
$105 nightly
The price is $119
Jul 27 - Jul 28
Total includes taxes and fees
Hilton Garden Inn Winchester
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Enjoy dining at this stylish restaurant with a central bar, high-top tables, and cozy booths.

DoubleTree by Hilton Front Royal Blue Ridge Shadows

4.0 star property
9.0 out of 10, Wonderful, (1001)
"Great stay, great location. "
$121 nightly
The price is $133
Jul 24 - Jul 25
Total includes taxes and fees
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Holiday Inn Express Hotel & Suites Winchester by IHG
Relax by the pool, surrounded by a spacious deck and a clear water's edge.

Holiday Inn Express Hotel & Suites Winchester by IHG

2.5 star property
8.8 out of 10, Excellent, (762)
"Very friendly staff and clean property"
$111 nightly
The price is $121
Jul 19 - Jul 20
Total includes taxes and fees
Holiday Inn Express Hotel & Suites Winchester by IHG
Holiday Inn Express Winchester South-Stephens City by IHG
Guests can check in at the hotel's prominent entrance, surrounded by ample parking.

Holiday Inn Express Winchester South-Stephens City by IHG

2.5 star property
8.2 out of 10, Very Good, (755)
"Always great!"
$79 nightly
The price is $86
Jul 18 - Jul 19
Total includes taxes and fees
Holiday Inn Express Winchester South-Stephens City by IHG
Holiday Inn Winchester Se-Historic Gateway by IHG
Welcome to the Holiday Inn, featuring a modern architectural design with a flat roof and symmetrical facade.

Holiday Inn Winchester Se-Historic Gateway by IHG

3.0 star property
9.0 out of 10, Wonderful, (1003)
"Great location,the hotel was very nice and the breakfast was great."
$92 nightly
The price is $100
Jul 27 - Jul 28
Total includes taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG
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 Winchester

Find out more about Winchester

Discover top Winchester attractions

In Winchester, Virginia, travelers can explore a rich tapestry of history and natural beauty. Start your journey at the historic Old Town, where charming cobblestone streets are lined with boutique shops, art galleries, and inviting cafes. Don’t miss the George Washington’s Office Museum, which offers a glimpse into the past with artifacts from the early days of America. For nature lovers, the stunning Shenandoah Valley offers hiking and picturesque views, particularly at the nearby Cedar Creek and Belle Grove National Historical Park. Families will enjoy the interactive exhibits at the Museum of the Shenandoah Valley, where kids can engage with art and history in fun ways. Finally, unwind at the beautiful Jim Barnett Park, where you can picnic, play sports, or simply stroll through its lush landscapes. For accommodations, consider staying in the heart of Old Town, where you can easily walk to most attractions. Hotels here offer a blend of modern comforts and historic charm, ensuring that your family feels pampered with attentive service and convenient access to all the local delights.

Find the best hotels with connecting rooms in Winchester

For travelers seeking comfortable accommodations in Winchester, Virginia, that offer the convenience of connecting rooms, these hotels are excellent choices. Each hotel provides a variety of amenities tailored to enhance family and group stays.

The George Washington Hotel, A Wyndham Grand Hotel

  • Why it's great for extra space: The George Washington Hotel stands out for travelers seeking connecting rooms, with an impressive review rating of 9.4. This upscale hotel offers spacious connecting rooms, ideal for family gatherings or group travels. With a range of luxurious amenities, including a full-service spa and onsite dining options, guests will enjoy a sophisticated experience during their stay.
  • Other amenities: Guests can take advantage of valet parking and 24-hour fitness facilities for convenience. The hotel features complimentary internet access and offers express check-in for a smooth arrival process. With nearby skiing and golf options, outdoor enthusiasts will find plenty to enjoy. The hotel also includes premium bedding and a concierge service to assist with local attractions and dining recommendations.
  • 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

Quality Inn

  • Why it's great for extra space: Quality Inn is an excellent choice for guests requiring connecting rooms, recognized for its solid review rating of 9.2. This hotel offers a variety of room configurations that cater to families and groups, ensuring everyone has ample space. With free breakfast every day, guests can fuel up before heading out to explore Winchester.
  • Other amenities: In addition to connecting rooms, the hotel provides a 24-hour restaurant and fitness facilities to keep guests engaged. Free self-parking and additional pet-friendly options make it accessible for all types of travelers. Guests can enjoy conveniences such as free toiletries and daily housekeeping, while nearby golf courses add an extra layer of enjoyment for golf enthusiasts.
  • Nearby attractions: Stonewall Jackson's Headquarters - 2.55 miles, Handley Regional Library - 2.82 miles, Eastgate Plaza Shopping Center - 2.82 miles

Comfort Inn & Suites

  • Why it's great for extra space: Comfort Inn & Suites is an ideal choice for guests looking for connecting rooms, featuring a strong review rating of 9.2. This hotel provides comfortable, well-equipped rooms that can easily accommodate families or groups traveling together. With a complimentary breakfast served daily, guests can start their day right before exploring the area.
  • Other amenities: Alongside connecting room options, the hotel offers 24-hour fitness facilities to keep guests active during their stay. Free self-parking and off-street parking options ensure convenience for travelers. Guests will appreciate the traditional hotel design and a gift shop for any last-minute needs. The hotel is pet-friendly, allowing pets in rooms, making it a versatile choice for all types of travelers.
  • Nearby attractions: Appleland Sports Center - 1.32 miles, The Kernstown Battlefield - 2.23 miles, Shenandoah Valley Discovery Museum - 4.82 miles

Microtel Inn & Suites by Wyndham Winchester

  • Why it's great for extra space: Microtel Inn & Suites is an excellent option for travelers needing connecting rooms, receiving a solid review rating of 9.0. This hotel offers connecting room configurations, providing ample space for families or groups. Guests can enjoy a free breakfast daily and access to both an indoor pool and fitness facilities for relaxation and exercise.
  • Other amenities: Beyond connecting rooms, this hotel features free self-parking and convenient amenities like microwaves in each room. Guests can take advantage of the rollaway beds available for additional sleeping arrangements, while free toiletries and daily housekeeping ensure a comfortable stay. The hotel also offers early check-in and late check-out options for added flexibility.
  • Nearby attractions: Stonewall Jackson's Headquarters - 2.54 miles, Handley Regional Library - 2.7 miles, Eastgate Plaza Shopping Center - 2.71 miles

La Quinta Inn & Suites by Wyndham Winchester

  • Why it's great for extra space: La Quinta Inn & Suites is a fantastic option for travelers needing connecting rooms, a stellar review rating of 9.0. This hotel features spacious rooms with connecting room options, ensuring a comfortable stay for families or groups. Guests can also enjoy complimentary breakfast daily, an indoor pool, and a relaxing hot tub, making it perfect for unwinding after a day of exploration.
  • Other amenities: In addition to the connecting rooms, guests can take advantage of amenities like free parking, fitness facilities, and designer toiletries for a touch of luxury. The hotel provides Egyptian cotton sheets for a restful night's sleep, and for those traveling with pets, it offers pet-friendly accommodations. A terrace is available for guests to enjoy the outdoors, and nearby golf lessons and shopping districts add to the convenience of the location.
  • Nearby attractions: Valley Health - 0.69 miles, Shenandoah University - 0.13 miles, Apple Blossom Mall - 0.86 miles

Frequently asked questions

How much do hotels with connecting rooms in Winchester cost?
Hotels with connecting rooms in Winchester range from $86 to $133 per night. These stays provide lots of room for your entire crew at a price that fits your budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best hotels with connecting rooms in Winchester?
Winchester offers multiple hotels with connecting rooms with a total average guest review rating of 8.8. SpringHill Suites by Marriott Winchester comes highly rated if you're on the road with the kids or a group of your besties. Visitors staying at this 2.5-star hotel can enjoy amenities such as first-run movie services and a firepit. The George Washington Hotel, A Wyndham Grand Hotel is another popular choice. This 3.5-star hotel offers connecting rooms as well as a swimming pool and pillow top mattresses.
How many hotels with adjoining rooms are there in Winchester?
Lock in your vacation dates and then pick from 19 hotels with adjoining rooms in Winchester. For a business trip, a couples' getaway or anything in between, Expedia will help you find an ideal stay in just a click or two.
What are the best cheap hotels with connecting rooms in Winchester?
With hotels with connecting rooms starting from only $86 per night, you may be tempted to extend your stay in Winchester! One option that's easy on the hip pocket is SpringHill Suites by Marriott Winchester. It comes with the space you need as well as first-run movie services and a firepit. Another favorite is Hampton Inn Winchester-University/Mall Area. On top of connecting rooms, it offers a swimming pool and pool sun loungers. Exploring free attractions in Winchester will stretch your travel budget even further. Shenandoah University and Jim Barnett Park are on the itineraries of many tourists. With the money you save, why not sightsee some more? This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the top motels with connecting rooms in Winchester?
Round up the crew and head straight to Travelodge by Wyndham Winchester. This wallet-friendly motel with connecting rooms also includes free use of a nearby fitness center and free internet services, and is located just 2 mi south of downtown Winchester.When it's time to slip into some comfy sneakers and go sightseeing, head straight to Museum of the Shenandoah Valley. Shenandoah Valley Discovery Museum is another highlight in Winchester.
Are there any family-friendly hotels with connecting rooms in Winchester?
Settle in at Country Inn & Suites by Radisson, Winchester, VA, a 3-star option not far from town. Amenities here include complimentary breakfast and laundry facilities. Another family-friendly hotel with connecting rooms is Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel. Laundry facilities and a laundry service help make this 3-star stay a favorite among guests. Winchester has loads of family-friendly attractions to explore that'll keep the kids entertained. Shenandoah Valley Discovery Museum and Appleland Sports Center promise a fun-fueled day for both young and old.
Why book your hotel with connecting rooms in Winchester with Expedia?
We think that family vacays shouldn't be difficult, so if you're seeking hotels with connecting rooms at a competitive rate, Expedia has your back. Save cash and opt for a cozy motel with connecting rooms, or book a 5-star hotel and pamper your loved ones. Take advantage of our search filters to find a property in Winchester that suits your style.
How can I find cheap hotels with connecting rooms in Winchester?
With Expedia's filter tool, sourcing cheap hotels with connecting rooms in Winchester is a snap. To discover properties that are very pocket friendly, tailor your search results by budget, star rating and amenities.
What is there to do in Winchester near my hotel with connecting rooms?
Whatever you love to do, Winchester has a whole lot to keep you occupied. Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theater are on most travelers' trip plans. Don't miss Winchester Little Theater, Shenandoah University and Jim Barnett Park either. With Expedia's hotel deals in Winchester, you'll be able to discover even more renowned attractions like these with the cash you save.