Hotels with connecting rooms in The Berkshires, Massachusetts

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Check availability on The Berkshires Hotels with connecting rooms

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Sep 20 - Sep 21
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Sep 21 - Sep 22
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Sep 26 - Sep 28
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Oct 3 - Oct 5

Top The Berkshires Hotels with connecting rooms

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1010)
"The staff and location make it excellent"
The price is P7,226
P8,072 total
includes taxes & fees
Sep 29 - Sep 30
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Chestnut Lodge
Property grounds

Chestnut Lodge

3.5 star property
2.0 out of 10, (2)
"An absolutely horrible experience! My family (2 adults and my 6 year old son) had reserved this so-called hotel for $284 in June for a 13th Aug stay. After a full day at the Berkshires, we checked-in at 6 pm. This place is in a terrible location (unpaved roads, still-in construction steps). To our horror we found that the room had No Air-Conditioning. It was 90 degrees outside and all they had in the room was a ceiling fan. There were bugs in the room due to the heat. On top of it all the...
Chestnut Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (879)
"Our stay was very pleasant "
The price is P6,219
P6,947 total
includes taxes & fees
Oct 1 - Oct 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Quality Inn
Lobby

Quality Inn

2.5 star property
8.4 out of 10, Very Good, (1008)
"Great location and close enough to walk to shops and restaurants. "
The price is P5,286
P5,905 total
includes taxes & fees
Oct 13 - Oct 14
Quality Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lobby

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (736)
"Thank you for nice hospity. Staff was very friendly and professional."
The price is P9,072
P10,133 total
includes taxes & fees
Sep 24 - Sep 25
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1004)
"We enjoyed the quietness of the hotel and breakfast. It is very conveniantly located on RTR7/US20 but tucked off the road so its quiet "
The price is P7,711
P8,613 total
includes taxes & fees
Sep 28 - Sep 29
Hampton Inn & Suites Berkshires-Lenox
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (644)
"We always stay at the Garden Inn when visiting the Berkshires."
The price is P9,064
P10,125 total
includes taxes & fees
Sep 28 - Sep 29
Hilton Garden Inn Lenox Pittsfield
Hotel Downstreet, an Ascend Collection Hotel
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1008)
"Property was very clean and view of mountain from window was awesome beds very comfortable and loved the hot tub and pool"
The price is P8,678
P9,694 total
includes taxes & fees
Sep 22 - Sep 23
Hotel Downstreet, an Ascend Collection Hotel
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Premium bedding, pillowtop beds, in-room safe, desk

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (662)
"Very Good; Clean, Quiet Motel, Area has many dining options."
The price is P7,655
P8,550 total
includes taxes & fees
Sep 28 - Sep 29
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (771)
"Hotel on North punches above its weight. It's a great hotel in an OK downtown. "
The price is P9,072
P10,133 total
includes taxes & fees
Sep 28 - Sep 29
Hotel On North
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

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"We come here regularly. We are satisfied with its price and location."
Andrew 1-night trip
Posted 3 days ago
Hotel Downstreet, an Ascend Collection Hotel

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Frequently asked questions

How much do hotels with connecting rooms in The Berkshires cost?
You can expect to pay from P5,905 to P10,133 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 8.8. 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.