Hotels with connecting rooms, The Berkshires Massachusetts

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Our top choices for The Berkshires hotels with connecting rooms

42-inch flat-screen TV with cable channels, TV

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

1. The Yankee Inn

Lenox

Larry

P10,023

P11,196 total

includes taxes & fees

Sep 7 - Sep 8

2. The Red Lion Inn

Stockbridge

Merideth

P9,622

P13,766 total

includes taxes & fees

Sep 9 - Sep 10

1 bedroom, premium bedding, pillowtop beds, desk

3. Quality Inn Great Barrington

Great Barrington

Lynn

P5,628

P6,287 total

includes taxes & fees

Sep 2 - Sep 3

Premium bedding, pillowtop beds, in-room safe, desk

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

Great Barrington

Kathleen

P7,497

P8,375 total

includes taxes & fees

Sep 9 - Sep 10

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

Lee

James

P8,158

P9,113 total

includes taxes & fees

Sep 7 - Sep 8

Premium bedding, minibar, in-room safe, desk

6. Hotel On North

Pittsfield

Dragana

P10,874

P12,146 total

includes taxes & fees

Sep 7 - Sep 8

7. The Cornell Inn, Lenox & The Berkshires

Lenox

Edward

P10,804

P12,430 total

includes taxes & fees

Aug 31 - Sep 1

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

Great Barrington

Lisa

P11,824

P13,208 total

includes taxes & fees

Aug 19 - Aug 20

View all properties

Top The Berkshires Hotel Reviews

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."

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."

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."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Love this hotel for going to Mass MoCA"

The Little Lion

10/10 Excellent

"Great location. Functional and affordable. Pet friendly."

Frequently asked questions

How much do hotels with connecting rooms in The Berkshires cost?

You can expect to pay from P6,287 to P18,024 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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Check availability on The Berkshires Hotels with connecting rooms

Our top choices for The Berkshires hotels with connecting rooms

1. The Yankee Inn

2. The Red Lion Inn

3. Quality Inn Great Barrington

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

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

6. Hotel On North

7. The Cornell Inn, Lenox & The Berkshires

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

9. Hotel Downstreet, an Ascend Collection Hotel

10. Hilton Garden Inn Lenox Pittsfield

Top The Berkshires Hotel Reviews

The Red Lion Inn

The Yankee Inn

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Hotel Downstreet, an Ascend Collection Hotel

The Little Lion

Frequently asked questions

Explore a world of travel with Expedia

Hotels with connecting rooms in The Berkshires, Massachusetts

Change your mind

Treat yourself

Be picky

Check availability on The Berkshires Hotels with connecting rooms

Our top choices for The Berkshires hotels with connecting rooms

1. The Yankee Inn

2. The Red Lion Inn

3. Quality Inn Great Barrington

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

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

6. Hotel On North

7. The Cornell Inn, Lenox & The Berkshires

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

9. Hotel Downstreet, an Ascend Collection Hotel

10. Hilton Garden Inn Lenox Pittsfield

Top The Berkshires Hotel Reviews

The Red Lion Inn

The Yankee Inn

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Hotel Downstreet, an Ascend Collection Hotel

The Little Lion

Frequently asked questions

Explore a world of travel with Expedia