Hotels with connecting rooms in The Berkshires, Massachusetts

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Hotels with connecting rooms

Tonight
Nov 5 - Nov 6
Tomorrow
Nov 6 - Nov 7
This weekend
Nov 7 - Nov 9
Next weekend
Nov 14 - Nov 16

Top The Berkshires Hotels with connecting rooms

Exterior
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1030)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
The price is P6,374
P7,119 total
includes taxes & fees
Dec 6 - Dec 7
The Yankee, Trademark Collection by Wyndham
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very Good, (941)
"Spotless and friendly staff"
United States
Nikisha
The price is P6,028
P6,734 total
includes taxes & fees
Nov 16 - Nov 17
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Front of property - evening/night
Hotel On North
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (791)
"Perfect Stay in the Berkshire This hotel was spacious, clean, and had everything needed for a comfortable stay. The room was well-maintained, and the location was ideal—close to local attractions and easy to get around. Smooth check-in process and great access throughout. Highly recommend! "
United States
Ann
The price is P7,790
P8,701 total
includes taxes & fees
Nov 20 - Nov 21
Hotel On North
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8 out of 10, Excellent, (688)
"This motel was easy access right off the highway, super clean, and the staff was great. We would definitely stay here again. Breakfast options were good as well. "
United States
Tina
The price is P6,291
P7,027 total
includes taxes & fees
Nov 30 - Dec 1
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1000)
"Good for one night stay"
United States
Marla
The price is P6,418
P7,169 total
includes taxes & fees
Dec 2 - Dec 3
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Terrace/patio
Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield
3.0 star property
9.2 out of 10, Wonderful, (656)
"Lovely hotel, room was great along with the staff and the grounds where beautiful. Thank you."
United States
Vicki
The price is P7,485
P8,360 total
includes taxes & fees
Nov 23 - Nov 24
Hilton Garden Inn Lenox Pittsfield
Exterior
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1000)
"The staff is very friendly and helpful "
United States
karin
The price is P6,508
P7,270 total
includes taxes & fees
Nov 16 - Nov 17
Hampton Inn & Suites Berkshires-Lenox
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.4 out of 10, Exceptional, (749)
"We had a nice stay at the Fairfield Inn in Great Barrington. It’s conveniently located not far from downtown and just a short drive to Stockbridge. The front desk staff was welcoming, the room spacious and clean, and plenty of breakfast items to choose from. Definitely recommend!"
United States
Denise
The price is P8,370
P9,349 total
includes taxes & fees
Nov 9 - Nov 10
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes
Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
8.8 out of 10, Excellent, (1006)
"Very clean and inviting Hotel located in downtown area. Very walkable area. Parking was free. Front desk very friendly and helpful. Would stay again."
United States
Tammy
The price is P8,408
P9,392 total
includes taxes & fees
Nov 25 - Nov 26
Hotel Downstreet, an Ascend Collection Hotel
Garden
Shaker Mill Inn
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (433)
"Nice place, easy check in"
United States
Robert
The price is P6,408
P7,030 total
includes taxes & fees
Nov 12 - Nov 13
Shaker Mill 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.
View all properties

Top The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"We truly enjoyed our stay. Our room was spacious, beds comfy and the charm and history of the inn is truly enchanting. "
Lori 1-night trip
Posted 2 days ago
The Red Lion Inn

Explore a world of travel with Expedia

Frequently asked questions

How much do hotels with connecting rooms in The Berkshires cost?
You can expect to pay from to 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 . 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 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.