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Find Hotels with Connecting Rooms in Stockbridge, MA

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Our top choices for Stockbridge hotels with connecting rooms

Exterior
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "
United States
Joyce
$180 nightly
The price is $202
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Red Lion Inn
Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
$131 nightly
The price is $146
Dec 22 - Dec 23
Total with taxes and fees
Element Lenox Berkshires
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
$100 nightly
The price is $110
Dec 14 - Dec 15
Total with taxes and fees
Shaker Mill Inn
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1002)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
$75 nightly
The price is $84
Dec 24 - Dec 25
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (65)
"Very clean room, courteous staff. "
United States
Jeffrey
$113 nightly
The price is $126
Jan 11 - Jan 12, 2026
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
$101 nightly
The price is $113
Dec 23 - Dec 24
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (986)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$93 nightly
The price is $104
Dec 16 - Dec 17
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1002)
"Clean room, nice location "
United States
Devron
$76 nightly
The price is $85
Dec 28 - Dec 29
Total with taxes and fees
Quality Inn Great Barrington
Lobby lounge
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
$103 nightly
The price is $115
Dec 14 - Dec 15
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
$103 nightly
The price is $115
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
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.
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Find out more about Stockbridge

Discover top Stockbridge attractions

Stockbridge, Massachusetts, is a charming New England town brimming with cultural and outdoor experiences. Start your exploration at the Norman Rockwell Museum, where you can admire the beloved artist's iconic works and learn about his significant impact on American culture. For a taste of local history, visit the historic Chesterwood estate, once home to sculptor Daniel Chester French, which offers beautiful grounds and insightful tours. Enjoy a leisurely stroll through the picturesque Stockbridge Bowl, perfect for a family picnic or kayaking, where the serene waters reflect the surrounding mountains. Take a hike in the nearby Berkshire Mountains, offering trails suited for all skill levels, with stunning views that make for great family photos. Finally, don't miss a visit to the delightful shops and restaurants along Main Street, where you can indulge in local flavors and artisanal crafts. For an enriching stay, consider accommodations in the heart of Stockbridge, where you’ll find charming inns and boutique hotels offering personalized service. Many properties provide family-friendly amenities and are conveniently located near these attractions, allowing you to explore the town with ease. After a day of adventure, unwind in your cozy room or enjoy the scenic views from your balcony, ensuring your family feels pampered and well taken care of throughout your visit.

Find the best hotels with connecting rooms in Stockbridge

For travelers visiting Stockbridge, Massachusetts, seeking accommodations with connecting rooms, The Red Lion Inn stands out as a welcoming option. This historic hotel offers family-friendly amenities while maintaining a charming atmosphere.

The Red Lion Inn

  • Why it's great for extra space: The Red Lion Inn is an excellent choice for travelers looking for connecting rooms, with a solid guest review rating of 8.8. This hotel offers connecting room options that are perfect for families or groups, ensuring everyone stays together while enjoying the comfort of their own space. The historic charm and inviting ambiance make it a delightful retreat in Stockbridge.
  • Other amenities: Guests can enjoy a range of features such as an outdoor pool for relaxation, a full-service spa offering soothing treatments, and cozy fireplaces in select rooms for added comfort. The hotel also provides complimentary cribs for families, concierge services to assist with local arrangements, and evening entertainment options. Nearby, guests can explore skiing, snowboarding, and tubing activities, making it a great location for winter enthusiasts.
  • Nearby attractions: Housatonic River - 0.13 miles, Berkshire Theatre Festival - 0.51 miles, Naumkeag Museum - 0.64 miles

Top Stockbridge Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"My husband and I needed a night away between the holidaze and it was perfect! Cozy, clean and warm fireplace to nurture us during a cold snap! Shelly went above and beyond to ensure that we were comfortable and in the quietest part of the hotel. We are booking our family members there"
Sara 1-night trip
Posted 3 days ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

How much do hotels with connecting rooms in Stockbridge cost?
You'll pay from $84 to $202 per night for hotels with connecting rooms in Stockbridge. No matter your budget, a terrific stay is a click away on Expedia. 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 Stockbridge?
Stockbridge offers multiple hotels with connecting rooms with a total average guest review rating of 9.0. Hilton Garden Inn Lenox Pittsfield comes highly rated if you're vacationing with the kids or as a group. Guests of this 3-star hotel can enjoy conveniences such as a swimming pool and an electric car charging station. Hampton Inn & Suites Berkshires-Lenox is also very popular. This 2.5-star hotel offers connecting rooms and also has mountain views and pool sun loungers.
How many hotels with adjoining rooms are there in Stockbridge?
Choose from 1 hotels with adjoining rooms in Stockbridge. No matter if you're vacationing with the family or organizing a weekend break with your pals, Expedia can help you find the right space for your whole crew.
What are the best cheap hotels with connecting rooms in Stockbridge?
Hotels with connecting rooms start at only $84 per night, so your Stockbridge getaway doesn't have to take a big chunk out of your finances! Hampton Inn & Suites Berkshires-Lenox is a wallet-friendly option that offers plenty of amenities, including pool sun loungers and a swimming pool. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires is another one of our popular hotels with connecting rooms. You'll welcome conveniences such as a swimming pool and front desk services. When you're ready to discover Stockbridge, don't miss National Shrine of the Divine Mercy. This terrific attraction is free if you'd also like to sightsee on the cheap. 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 Stockbridge?
Pack your suitcase and make The Briarcliff Motel the base for your next memorable adventure. Offering a garden and complimentary breakfast, this motel with connecting rooms is around 3 mi south of downtown Stockbridge. Travelodge by Wyndham Great Barrington Berkshires is another option that'll suit your needs. Located around 4 mi south of the city center, amenities here include a garden and a barbecue grill.With so many dining, shopping and cultural opportunities to squeeze into your Stockbridge itinerary, it can be difficult to know where to begin. Norman Rockwell Museum and Berkshire Theatre Festival are excellent places to get going on your sightseeing adventures.
Are there any family-friendly hotels with connecting rooms in Stockbridge?
Settle in at Hilton Garden Inn Lenox Pittsfield, a 3-star option just a short drive from downtown. Amenities here include a laundry service and housekeeping services. Another family-friendly hotel with connecting rooms is Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires. A playground and complimentary breakfast help make this 2.5-star property a guest favorite. Once you've checked in and dropped off your things, there's a host of family-friendly attractions to explore around Stockbridge. Pleasant Valley Wilderness Sanctuary and Berkshire Scenic Railway Museum are two of our top suggestions.
Why book your hotel with connecting rooms in Stockbridge with Expedia?
Booking a hotel with connecting rooms in Stockbridge is as easy as deciding on your travel dates and choosing an option that suits your style. Chasing something luxurious or affordable, or a stay that also offers a pool? Use Expedia's search filters to narrow your results even further and find your dream fit.
How can I find cheap hotels with connecting rooms in Stockbridge?
A wonderful way to track down cheap hotels with connecting rooms in Stockbridge is with Expedia's nifty filter tool. Refine your search by amenities, star rating and budget to nab excellent rates in a couple of clicks.
What is there to do in Stockbridge near my hotel with connecting rooms?
You'll find plenty of awesome things to see and do in Stockbridge. Head for major attractions like Norman Rockwell Museum, Berkshire Theatre Festival and Naumkeag Museum. Mission House, Schantz Galleries and National Shrine of the Divine Mercy also appeal to many visitors.

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