Top 10 The Berkshires Hotels with Air Conditioning for 2026

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Our top choices for The Berkshires hotels with air conditioning

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

Desk, laptop workspace, iron/ironing board, free WiFi

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

1. The Yankee Inn

Lenox

Karen

RM642

RM717 total

includes taxes & fees

14 Sept - 15 Sept

2. Berkshires Untold

Lenox

Pamela

RM519

RM580 total

includes taxes & fees

9 Sept - 10 Sept

Iron/ironing board, free cots/infant beds, WiFi, bed sheets

3. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Claudia

RM475

RM610 total

includes taxes & fees

3 Sept - 4 Sept

4. Berkshire Mountain Lodge

Pittsfield

Robert

RM384

RM520 total

includes taxes & fees

31 Aug - 1 Sept

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

Lee

James

RM518

RM578 total

includes taxes & fees

14 Sept - 15 Sept

1 bedroom, premium bedding, pillow-top beds, desk

6. Quality Inn Great Barrington

Great Barrington

Lynn

RM376

RM420 total

includes taxes & fees

9 Sept - 10 Sept

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

Pittsfield

Ken

RM516

RM576 total

includes taxes & fees

14 Sept - 15 Sept

8. The Red Lion Inn

Stockbridge

Patricia

RM675

RM956 total

includes taxes & fees

14 Sept - 15 Sept

View all properties

Top The Berkshires Hotel Reviews

The Red Lion Inn

10/10 Excellent

"Perfect."

Howard Johnson by Wyndham Lenox

8/10 Good

"The motel is in a great location. You could walk to everything. The room was clean and comfortable although the air conditioning in the room didn't work very well. The fan ran but it didn't cool the room."

Jiminy Peak Mountain Resort

10/10 Excellent

"…."

Hotel On North

10/10 Excellent

"A great location for a concert at Tanglewood and a chance to explore a new city. Parking is easy and convenient. The staff is very welcoming and helpful. The facilities are clean, modern, quiet, and vintage at the same time. A beautiful bar and restaurant on site and many restaurants and coffee shops in walking distance. I would definitely stay here again!"

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"0nly 1 of 3 elevators was working. It was a 11 story building, and there was a lot of waiting. My room was wonderful, very clean, and with a fabulous view."

Frequently asked questions

How much do hotels with air conditioning in The Berkshires cost?

Hotels with air conditioning in The Berkshires range between RM420 and RM956 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 9.2, 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 RM420 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 kilometers 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 kilometers 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.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on The Berkshires Hotels with Air Conditioning

Our top choices for The Berkshires hotels with air conditioning

1. The Yankee Inn

2. Berkshires Untold

3. Holiday Inn Club Vacations Oak 'n Spruce Resort

4. Berkshire Mountain Lodge

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

6. Quality Inn Great Barrington

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

8. The Red Lion Inn

9. Hotel On North

10. Vacation Village in the Berkshires

Top The Berkshires Hotel Reviews

The Red Lion Inn

Howard Johnson by Wyndham Lenox

Jiminy Peak Mountain Resort

Hotel On North

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

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