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Hotels with connecting rooms in The Berkshires, Massachusetts

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Check availability on The Berkshires Hotels with connecting rooms

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22

Our top choices for The Berkshires hotels with connecting rooms

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

1. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (821 reviews)
"Nice view and location for fall color."
United States
Md
The price is P10,129
P11,314 total
includes taxes & fees
Nov 12 - Nov 13
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

2. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (854 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
The price is P5,233
P5,845 total
includes taxes & fees
Dec 7 - Dec 8
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

3. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (942 reviews)
"Clean, reasonably priced, convenient"
United States
Martha
The price is P3,773
P4,215 total
includes taxes & fees
Nov 9 - Nov 10
Monument Mountain Motel
A grassy area with a lake, trees, and red chairs arranged around a fire pit.

4. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.8 out of 10, Exceptional, (27 reviews)
"excellent lakeside view"
United States
mike
The price is P6,877
P7,682 total
includes taxes & fees
Nov 9 - Nov 10
Berkshire Lake Lodge
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

5. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,003 reviews)
"Just perfect lodging place for short time travelers"
United States
Bernardo Jr
The price is P5,348
P5,974 total
includes taxes & fees
Dec 2 - Dec 3
Quality Inn Lee - Lenox South
A lodge with a large building and a dock by a lake, surrounded by forest.

6. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,001 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
The price is P6,752
P7,542 total
includes taxes & fees
Dec 3 - Dec 4
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

7. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,003 reviews)
"Nice place to stay"
United States
Michael
The price is P7,377
P9,472 total
includes taxes & fees
Nov 10 - Nov 11
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

8. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (58 reviews)
"East Rock was a nice, clean, and comfortable place to stay. Everything was great, and I enjoyed my stay."
United States
Sharon
The price is P7,667
P8,564 total
includes taxes & fees
Dec 9 - Dec 10
East Rock Inn
Interior detail

9. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
United States
Liliana
The price is P10,939
P12,219 total
includes taxes & fees
Nov 11 - Nov 12
Wilder House Berkshires
A white two-story house with a front door, windows, and a chimney.

10. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (96 reviews)
"Lovely property.unique historic buildings and rooms with updated amenities! Quiet and peaceful beautiful dinner!"
United States
mary ellen
The price is P18,284
P22,063 total
includes taxes & fees
Nov 9 - Nov 10
The Old Inn On The Green
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

11. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (688 reviews)
"Great stay!"
United States
Vandhana
The price is P7,919
P8,846 total
includes taxes & fees
Nov 15 - Nov 16
Courtyard by Marriott Lenox Berkshires
An indoor swimming pool with clear water, tiled floors, and a blue wall.

12. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (257 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
The price is P6,494
P7,254 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

13. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (51 reviews)
"Clean, spacious room Accommodating staff especially Shawn and Jennifer at the front desk. Very nice pool and gym Definitely coming back"
United States
Francis
The price is P8,511
P9,507 total
includes taxes & fees
Nov 15 - Nov 16
Element by Marriott Lenox Berkshires
Exterior

14. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,259 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is P4,839
P6,814 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

15. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,003 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is P4,770
P5,328 total
includes taxes & fees
Nov 29 - Nov 30
Quality Inn Great Barrington
A four-poster bed with a canopy, bedside lamps, a bedside table, a microwave, and a door in a hotel room.

16. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"The location was good for our trip."
United States
Basil
The price is P8,007
P8,944 total
includes taxes & fees
Nov 20 - Nov 21
The Yankee Inn
A multi-story hotel with a classic facade, large windows, and a prominent entrance.

17. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (981 reviews)
"Very nice hotel"
United States
Philip
The price is P7,320
P8,176 total
includes taxes & fees
Nov 29 - Nov 30
Hotel On North
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

18. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,067 reviews)
"Very nice place beautiful view"
United States
Brian
The price is P6,630
P7,405 total
includes taxes & fees
Nov 17 - Nov 18
Berkshires Untold
A spacious hotel lobby with multiple seating areas, large windows, and a television.

19. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,003 reviews)
"Breakfast was great"
United States
Thomas
The price is P6,913
P7,722 total
includes taxes & fees
Nov 15 - Nov 16
Hampton Inn & Suites Berkshires-Lenox
A hotel patio with outdoor seating and a fire pit.

20. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (716 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is P7,483
P8,358 total
includes taxes & fees
Nov 15 - Nov 16
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.
View all properties

Top The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"We stayed in an adjacent house owned by the hotel. When we booked we assumed we’d be in the main hotel. The “out” building was unmarked and hard to find. It was dark when we arrived and there were no porch lights. We thought the overall experience was good. Quaint but this building could benefit from some upgrades."
Randall 1-night trip
Posted 14 hours ago
The Red Lion Inn

Frequently asked questions

How much do hotels with connecting rooms in The Berkshires cost?
You can expect to pay from P5,328 to P14,226 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 9.0. 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.

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