A person snowboarding down a snowy slope.

The Berkshires Hotel Guide - Hotels with Air Conditioning in The Berkshires, Massachusetts

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Hotels with Air Conditioning

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for The Berkshires hotels with air conditioning

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
William
€105
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A garden with wooden Adirondack chairs and a stone pathway.
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
United States
Jay
€105
includes taxes & fees
18 Oct - 19 Oct
Berkshire Mountain Lodge
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A dining area with large windows, wooden furniture, and a view of a lake.
A lodge with a large building and a dock by a lake, surrounded by forest.
A lakeside lodge with a dock, fishing rods, and outdoor seating.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Bob
€115
includes taxes & fees
1 Nov - 2 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A modern cafe with a counter, seating area, and large windows.

4. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Sheldon
€98
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
A row of white plastic chairs on a covered outdoor area with a white building in the background.
A hotel room with a wooden dresser, a television, a microwave, and a mirror.
A motel with a parking lot and several cars parked.

5. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
United States
Victor
€59
includes taxes & fees
2 Nov - 3 Nov
Monument Mountain Motel
A building with a porch and multiple windows, surrounded by purple flowers.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A café with a display case, a frozen food section, and a marketplace sign.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

6. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Jared
€126
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Club Vacations Oak 'n Spruce Resort
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A dining area with a glass table, red walls, and framed artwork.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

7. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
€157
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
A cozy library with bookshelves, a fireplace, and comfortable seating.

8. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
€131
includes taxes & fees
1 Nov - 2 Nov
Berkshires Untold
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
A covered outdoor area with stone pillars and a view of a road and green hills.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

9. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
€125
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.
Indoor pool
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

10. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Jacob
€95
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
View all properties

Top The Berkshires Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Delightful place with charm and warmth and character. I would love to come back."
Richard 1-night trip
Posted 9 hours ago
Hotel On North
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Great place great price!"
James 1-night trip
Posted 17 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

8/10 Good
"Room was nice but did not have the view I was hoping for. Another hotel property is mostly blocking views from Yankee Inn looking West; the direction rooms with balcony’s face. The location near"
Theresa 2-night trip
Posted 18 hours ago
The Yankee Inn
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"My impression s? It’s a quiet rural area, but I am impressed how quiet the motel was. Not all the time, but occasionally it get noisy. I also liked the area."
Casey A 4-night trip
Posted 2 days ago
Best Western Plus Berkshire Hills Inn & Suites
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Staff very pleasant and helpful. On site restaurant was good and reasonably priced. Room was large with a nice view. Breakfast, which is continental, seemed a bit skimpy. Plenty of parking and in a great central area with many restaurants."
Francesca 1-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."
Peter 1-night trip
Posted 4 days ago
Quality Inn Great Barrington

Frequently asked questions

How much do hotels with air conditioning in The Berkshires cost?
Hotels with air conditioning in The Berkshires range between €59 and €157 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 9.1, so you'll easily discover a place that suits your needs. Organising 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 favourite. Whether you're planning a holiday 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 €59 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 travellers plenty of comfort and convenience, motels with air conditioning in The Berkshires are an affordable way to holiday with all the crew. If your travels are taking you to Williamstown, check out the availability at Maple Terrace Motel. It's 2 kilometres southeast of downtown and has amenities like mountain views and a garden. Another top option that has air conditioning is Cosy Corner Motel. It also offers a barbecue grill and a garden and is located about 3 kilometres north of the centre 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 Holidays Oak n' Spruce Resort in the Berkshires, an IHG Hotel. This 3.5-stars option is a favourite 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 Centre 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.

Explore a world of travel with Expedia