Hotels with connecting rooms in The Berkshires, Massachusetts

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Check availability on The Berkshires Hotels with connecting rooms

Tonight
Jul 30 - Jul 31
Tomorrow
Jul 31 - Aug 1
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Top The Berkshires Hotels with connecting rooms

The Cornell Inn, Lenox & The Berkshires
Traditional two-story house with a welcoming porch and balcony, set amidst snow-covered trees.

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is P7,643
P10,780 total
includes taxes & fees
Aug 27 - Aug 28
The Cornell Inn, Lenox & The Berkshires
Hampton Inn Bennington
Welcome to Hampton Inn, featuring a modern design with a covered entrance and 16-foot clearance.

Hampton Inn Bennington

2.5 star property
8.6 out of 10, Excellent, (1000)
"Easy parking. Inn was in a great location allowing for a centralized hub for our day trips. "
The price is P9,186
P10,012 total
includes taxes & fees
Aug 17 - Aug 18
Hampton Inn Bennington
Hilton Garden Inn Lenox Pittsfield
Relax on the patio with wicker sofas and armchairs, surrounded by a fire feature and a beautiful garden view.

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is P11,806
P13,187 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Garden Inn Lenox Pittsfield
Hampton Inn & Suites Greenfield
Two beds with crisp linens, a desk with TV, microwave, and refrigerator, and a window with a view.

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (821)
"Great property and staff!"
The price is P10,195
P11,388 total
includes taxes & fees
Aug 11 - Aug 12
Hampton Inn & Suites Greenfield
Quality Inn Westfield - Springfield
Relax in a stylish space with a seating area, wooden desk, and large windows offering a view of the outdoors.

Quality Inn Westfield - Springfield

2.5 star property
7.2 out of 10, Good, (822)
"The price was good for a clean room and nice breakfast."
The price is P5,589
P6,243 total
includes taxes & fees
Aug 17 - Aug 18
Quality Inn Westfield - Springfield
Shaker Mill Inn
Step into the charming Shaker Mill Inn, surrounded by lush greenery and a beautiful garden.

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (418)
"Very cute and clean room. After driving all day we were so happy to see all muffins, scones, yogurt, cereal, oatmeal, strawberries, milk, OJ, hot chocolate and coffee already in the room for breakfast the next day. We had a great stay, thank you!"
The price is P10,864
P11,918 total
includes taxes & fees
Aug 4 - Aug 5
Shaker Mill Inn
Harbour House Inn
Stunning traditional architecture with a central entrance and beautifully landscaped surroundings.

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is P14,998
P15,853 total
includes taxes & fees
Aug 12 - Aug 13
Harbour House Inn
1896 House Country Inn & Motels
Welcome to The 1896 House, a serene retreat managed by Brookside Accommodations.

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (430)
"Near hiking for Mt. Greylock and the Appalachian Trail. Nice walking area close by at Lamb's Hill. Clean Older mattress, was OK, but could feel springs a little. If you like a tub, it is tiny. The shower is OK"
1896 House Country Inn & Motels
Simsbury Inn
Stroll through the serene garden, surrounded by lush greenery and a central fountain.

Simsbury Inn

3.5 star property
9.2 out of 10, Wonderful, (262)
"Excellent all around. Staff could not have been more helpful."
The price is P13,094
P16,307 total
includes taxes & fees
Jul 31 - Aug 1
Simsbury Inn
Kitzhof Inn
Welcome to the pet-friendly Kitzhof Inn, where rooms are available for guests with their furry friends.

Kitzhof Inn

2.5 star property
9.2 out of 10, Wonderful, (224)
"We would stay again if ever traveling in the area!! The staff were awesome. We walked to the bar just down and across the road. Awesome food and drinks there too."
Kitzhof Inn
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.

Top The Berkshires Hotel Reviews

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

10/10 Excellent
"All good"
Elaina 1-night trip
Posted 3 days ago
Hotel Downstreet, Ascend Hotel Collection

Frequently asked questions

How much do hotels with connecting rooms in The Berkshires cost?
You can expect to pay from P5,784 to P11,806 per night for hotels with connecting rooms in The Berkshires. Whatever your budget, you'll find the perfect stay 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 The Berkshires?
The Berkshires has multiple hotels with connecting rooms, with a total average guest review rating of 8.8. Organizing an escape to Lenox? Put your bags down at Hotel On North, a popular 3.5-star option with mountain views and a restaurant. Another highly recommended choice with connecting rooms is Hilton Garden Inn Lenox Pittsfield. It has a 3-star rating and conveniences that include a terrace and a swimming pool.
How many hotels with adjoining rooms are there in The Berkshires?
The Berkshires has 27 hotels with adjoining rooms on offer. Enter your destination and travel dates and book your ideal vacation today.
What are the top motels with connecting rooms in The Berkshires?
Providing guests with extra space and convenience, motels with connecting rooms in The Berkshires are a budget-friendly way to vacation with your whole crew. If you're eager to visit Williamstown, book a few days at Willows Motel Williamstown. It's 2 kilometers southeast of downtown and includes amenities like a garden and a terrace. Another top pick is Williamstown Motel. It has a barbecue grill and individually decorated rooms and is located about 2 kilometers southeast of the center of Williamstown.There are plenty of things to keep you entertained in Williamstown. Williamstown Theatre Festival and Sterling and Francine Clark Art Institute are two great places to start.
Are there any family-friendly hotels with connecting rooms in The Berkshires?
There sure are, so gather the family and start planning that trip to The Berkshires! If Lenox is on your travel itinerary, stay at Hotel On North. This 3.5-star option is a favorite family-friendly hotel with connecting rooms. It also comes with room service and housekeeping services. Another excellent choice is Hilton Garden Inn Lenox Pittsfield. Also in Lenox, it has a 3-star rating and comes with housekeeping services, laundry facilities and connecting rooms. Lenox has tons of family-friendly attractions when you're ready to sightsee. Hancock Shaker Village and Berkshire Museum will keep your crew entertained.
Why book your hotel with connecting rooms in The Berkshires with Expedia?
Booking a hotel with connecting rooms in The Berkshires is as simple as clicking on your travel dates and picking an option that meets your requirements. After something luxurious or low cost, or a stay that also includes free WiFi? Use Expedia's search filters to further narrow your search results and find the perfect fit.
How can I find cheap hotels with connecting rooms in The Berkshires?
Expedia can help you narrow your search for cheap hotels with connecting rooms in The Berkshires. To reserve the perfect stay in a matter of clicks, try out our convenient filter tool to tailor your search results by star rating, amenities and budget.
What is there to do in The Berkshires near my hotel with connecting rooms?
Whatever you're into, there are almost endless things to put on your to-do list in The Berkshires. If you're vacationing in Williamstown, be sure to look around Sterling and Francine Clark Art Institute, Williams College Museum of Art and Hopkins Observatory. Escaping to Pittsfield? Bousquet Ski Area, Barrington Stage Company and Berkshire Museum are some major attractions here.