Photo by Photo courtesy of Berkshire Visitors Bureau

Hotels with Air Conditioning in The Berkshires, Massachusetts

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Check availability on The Berkshires Hotels with Air Conditioning

Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for The Berkshires hotels with air conditioning

Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is P5,443
P6,080 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Yankee, Trademark Collection by Wyndham
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2184)
"Awesome for ski"
United States
Lazar
The price is P6,108
P7,467 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Vacation Village in the Berkshires
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is P6,100
P6,814 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (796)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is P5,797
P7,788 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Berkshire Mountain Lodge
Interior
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (821)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is P7,440
P8,311 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Berkshires Untold
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (759)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is P7,931
P8,859 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Front of property - evening/night
Hotel On North

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (809)
"Clean room and staff was super friendly"
United States
Yuen
The price is P8,753
P9,777 total
includes taxes & fees
Dec 29 - Dec 30
Hotel On North
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is P7,513
P8,391 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hilton Garden Inn Lenox Pittsfield
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (999)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is P5,181
P5,788 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (809)
"Convenient location, very roomy, well equipped kitchen. "
United States
Carolyn
The price is P7,508
P9,535 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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

10/10 Excellent
"Wonderful stay in a winter wonderland that evening especially with use of the heated pool and hot tub being maintained! Loved it. Shops inside were lovely as well, bars & restaurant on-site were fun with quirky decor. Whole hotel is quirky, which is fun!"
Chris 1-night trip
Posted 1 day ago
The Red Lion Inn

Frequently asked questions

How much do hotels with air conditioning in The Berkshires cost?
Hotels with air conditioning in The Berkshires range between P5,788 and P9,777 per night. These escapes provide the comfort you desire at a price that's friendly on the pocket. 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 air conditioning in The Berkshires?
There are multiple hotels with air conditioning in The Berkshires with a total average guest review rating of 8.9, so you'll easily discover a place that suits your needs. Organizing a trip to Lenox? Look into Hotel On North. This highly rated 3.5-stars hotel features air conditioning to ensure a comfortable time, mountain views and laundry services. Hilton Garden Inn Lenox Pittsfield is another popular air-conditioned property with visitors to the area. A terrace and a swimming pool. Are other helpful amenities at this 3-stars option in Lenox.
How many hotels with air conditioning are there in The Berkshires?
Browse through our 105 hotels with air conditioning in The Berkshires and then select your favorite. Whether you're planning a vacation with all the fam or jet-setting with friends, with Expedia, your perfect stay is just clicks away.
What are the best cheap hotels with air conditioning in The Berkshires?
It all depends on which part of The Berkshires you want to visit! If you're headed to Lenox, Hampton Inn & Suites Berkshires-Lenox is a wonderful choice. Besides air conditioning, this pocket-friendly escape has pool sun loungers and mountain views. Spending some time in Williamstown? Berkshire Valley Inn is a thrifty getaway with AC in this city. Mountain views and front desk services are other amenities at this stay. Hotels with air conditioning start at P5,788 per night, which means your getaway doesn't have to make a big dent in your finances! Love to sightsee around The Berkshires without the high admission prices? Add some terrific free attractions to your itinerary, like Canoe Meadows Wildlife Sanctuary in Lenox. Williamstown also has plenty of things to do that don't cost anything, including Mount Greylock. This price was 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 top motels with air conditioning in The Berkshires?
Offering travelers plenty of comfort and convenience, motels with air conditioning in The Berkshires are an affordable way to vacation with all the crew. If your travels are taking you to Williamstown, check out the availability at Maple Terrace Motel. It's 2 kilometers southeast of downtown and has amenities like mountain views and a garden. Another top option that has air conditioning is Cozy Corner Motel. It also offers a barbecue grill and a garden and is located about 3 kilometers north of the center of Williamstown.Lenox has all kinds of fantastic attractions. Stop by Norman Rockwell Museum and Bousquet Ski Area when it's time to see the sights.
Are there any family-friendly hotels with air conditioning in The Berkshires?
Yes, so gather the family and make plans for your next getaway in The Berkshires! If Lenox is your chosen destination, make a booking at Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires, an IHG Hotel. This 3.5-stars option is a favorite family-friendly retreat with air conditioning. In addition, it comes with a playground and miniature golf. Another great choice is The Black Swan Lee - Lenox, Ascend Hotel Collection. Also in Lenox, it has a 3-stars rating and includes complimentary breakfast, WiFi and air conditioning. After you've checked in to your room, it's time to get to know Lenox. Enjoy memorable moments at family-friendly attractions such as Hancock Shaker Village and Berkshire Museum.
Are there any 5-star hotels with air conditioning in The Berkshires?
There aren't any 5-star hotels with air conditioning in The Berkshires. But you will find some 4-star getaways that offer what you're looking for. If you're headed to the vibrant city of Lenox, you can't pass up Garden Gables Inn. Treatment rooms and concierge services are just two of its many conveniences. Also consider Hampton Terrace Inn. Air conditioning, a swimming pool and a terrace help make this 4-star property in Lenox a comfortable base.
Why book your hotel with air conditioning in The Berkshires with Expedia?
Expedia has epic deals on hotels with air conditioning in The Berkshires. If you have a certain budget, choose how much you're willing to spend and the preferred star rating of your hotel. Then use our handy filters to search for air-conditioned digs with amenities like a pool or free WiFi. We'll help you find the right stay whatever your bank balance or plans.
How can I find cheap hotels with air conditioning in The Berkshires?
With Expedia's helpful filter tool, sourcing cheap hotels with air conditioning in The Berkshires couldn't be simpler. To view properties with AC that'll make your wallet smile, narrow down your search by budget and star rating.
What is there to do in The Berkshires near my hotel with air conditioning?
The best accessory to pack for your The Berkshires escape is a well-thought-out itinerary! Shakespeare and Company, Pleasant Valley Wilderness Sanctuary and Tanglewood Music Center are some of the most popular things to do if you're visiting Lenox. Williamstown is also packed with superb attractions, such as Sterling and Francine Clark Art Institute. Need more ideas for your to-do list? Visit Williams College Museum of Art and Williamstown Historical Museum too.

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