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The Berkshires Hotel Guide - Hotels with Connecting Rooms in The Berkshires, Massachusetts

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Check availability on The Berkshires Hotels with Connecting Rooms

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

Our top choices for The Berkshires hotels with connecting rooms

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

1. 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 €60
includes taxes & fees
9 Nov - 10 Nov
Monument Mountain Motel
A calm lake at dusk with a wooden dock and two chairs facing the water.

2. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.8 out of 10, Exceptional, (27 reviews)
"excellent lakeside view"
United States
mike
The price is €109
includes taxes & fees
9 Nov - 10 Nov
Berkshire Lake Lodge
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

3. 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 €107
includes taxes & fees
3 Dec - 4 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

4. 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 €83
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

5. 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 €161
includes taxes & fees
12 Nov - 13 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

6. 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 €85
includes taxes & fees
2 Dec - 3 Dec
Quality Inn Lee - Lenox South
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 €135
includes taxes & fees
10 Nov - 11 Nov
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 €122
includes taxes & fees
9 Dec - 10 Dec
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 €174
includes taxes & fees
10 Nov - 11 Nov
Wilder House Berkshires
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

10. 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 €126
includes taxes & fees
15 Nov - 16 Nov
Courtyard by Marriott Lenox Berkshires
A dining area with round tables set for two, a fireplace, and a mural on the wall.

11. 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 €314
includes taxes & fees
9 Nov - 10 Nov
The Old Inn On The Green
Two Adirondack chairs facing a river with a forested hill in the background.

12. 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 €127
includes taxes & fees
20 Nov - 21 Nov
The Yankee Inn
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

13. 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 €105
includes taxes & fees
17 Nov - 18 Nov
Berkshires Untold
An indoor swimming pool with clear water, tiled floors, and a blue wall.

14. 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 €103
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Exterior

15. 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 €97
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

16. 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 €76
includes taxes & fees
29 Nov - 30 Nov
Quality Inn Great Barrington
A building entrance with a large planter with purple flowers and a small tree.

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 €116
includes taxes & fees
29 Nov - 30 Nov
Hotel On North
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

18. 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 €135
includes taxes & fees
15 Nov - 16 Nov
Element by Marriott Lenox Berkshires
A snow-covered outdoor area with a patio, seating, and a covered dining area.

19. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,003 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is €175
includes taxes & fees
9 Nov - 10 Nov
The Cornell Inn, Lenox & The Berkshires
A spacious hotel lobby with multiple seating areas, large windows, and a television.

20. 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 €110
includes taxes & fees
15 Nov - 16 Nov
Hampton Inn & Suites Berkshires-Lenox
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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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 €76 to €202 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. Organising 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 holiday 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 holiday with your whole crew. If you're eager to visit Williamstown, book a few days at Willows Motel Williamstown. It's 2 kilometres 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 kilometres southeast of the centre 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 favourite 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 holidaying 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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