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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

Tonight
11 Aug - 12 Aug
Tomorrow
12 Aug - 13 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

Our top choices for The Berkshires hotels with connecting rooms

Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub
Superior Room, 1 King Bed, Jetted Tub
View from room
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

1. The Yankee Inn

The Yankee Inn
Lenox
United States
Larry
€160
includes taxes & fees
7 Sept - 8 Sept
The Yankee Inn
Exterior
Free daily continental breakfast
Lobby
Indoor pool

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
United States
Lisa
€188
includes taxes & fees
17 Aug - 18 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior
Free daily buffet breakfast
Premium bedding, pillow-top beds, in-room safe, desk
Indoor pool

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
United States
Kathleen
€119
includes taxes & fees
9 Sept - 10 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains
Coffee service
Exterior
Front of property

4. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
United States
William
€134
includes taxes & fees
9 Sept - 10 Sept
Hotel Downstreet, an Ascend Collection Hotel
Lobby
Standard Room, 2 Queen Beds, Non Smoking
Standard Room, 2 Queen Beds, Non Smoking
Exterior

5. Quality Inn Great Barrington

Quality Inn Great Barrington
Great Barrington
United States
Lynn
€90
includes taxes & fees
1 Sept - 2 Sept
Quality Inn Great Barrington
Reception hall
Indoor pool, pool loungers
Front of property
View from property

6. Simsbury Inn

Simsbury Inn
Simsbury Center
United States
Rachel
€257
includes taxes & fees
13 Aug - 14 Aug
Simsbury Inn
Lobby
Snack bar
Fitness facility
Free daily full breakfast

7. Hampton Inn Westfield

Hampton Inn Westfield
Westfield
United States
Karen
€116
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn Westfield
Indoor pool
Desk, blackout curtains, iron/ironing board, travel cot
Reception
Exterior

8. Hampton Inn Bennington

Hampton Inn Bennington
Bennington
United States
James
€169
includes taxes & fees
6 Sept - 7 Sept
Hampton Inn Bennington
Exterior
Bar (on property)
Exterior
Lobby

9. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Edward
€177
includes taxes & fees
25 Aug - 26 Aug
The Cornell Inn, Lenox & The Berkshires
Lake
Lake
Free daily continental breakfast
Lake

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
James
€130
includes taxes & fees
7 Sept - 8 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel
View all properties

Top The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This is an old inn. It’s elegant, fun and very comfortable. Lots of dark, antique furniture and communal card games. The staff is friendly and some have been there many years. Many of the guests return year after year. If that’s what you’re looking for, you will love it. I do. If you are looking for sleek and spotless, you are best suited elsewhere."
Melinda 1-night trip
Posted 8 hours ago
The Red Lion Inn
The Yankee Inn

The Yankee Inn

8/10 Good
"The room was clean. Linens in good shape. Good access to lots of activities nearby. Breakfast can be crowded. Go early."
Lucy 2-night trip
Posted 10 hours ago
The Yankee Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Hotel is currently under renovation which impacted parking and only 1 elevator available. Hotel staff, cleanliness and location excellent."
Myrna 1-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Love this hotel for going to Mass MoCA"
Victoria 1-night trip
Posted 3 days ago
Hotel Downstreet, an Ascend Collection Hotel
The Little Lion

The Little Lion

10/10 Excellent
"Great location. Functional and affordable. Pet friendly."
Anne 2-night trip
Posted 5 days ago
The Little Lion

Frequently asked questions

How much do hotels with connecting rooms in The Berkshires cost?
You can expect to pay from €90 to €257 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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