Top Chalets in Monterey in 2026

A lake surrounded by autumn-colored trees reflecting on the water.

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Recommended hotels in Monterey

Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

Pittsfield

William

includes taxes & fees

22 Jul - 23 Jul

Locust Tree Bed and Breakfast LLC

East Canaan

Larry

includes taxes & fees

12 Jul - 13 Jul

Berkshire Lake Lodge

Lee

Grzegorz

includes taxes & fees

30 Jul - 31 Jul

The Yankee Inn

Lenox

Mark

includes taxes & fees

6 Jul - 7 Jul

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

charles

includes taxes & fees

3 Aug - 4 Aug

Wilder House Berkshires

Sheffield

Jennifer

includes taxes & fees

7 Jul - 8 Jul

Exclusive Cottage | Iron/ironing board, free WiFi, bed sheets

Blackberry River Inn

Norfolk

Maura

includes taxes & fees

6 Jul - 7 Jul

Berkshire Inn

Pittsfield

Hannah

includes taxes & fees

6 Jul - 7 Jul

Berkshire Travel Lodge

Austerlitz

William

includes taxes & fees

12 Jul - 13 Jul

Quality Inn Great Barrington

Great Barrington

Braynd

includes taxes & fees

3 Aug - 4 Aug

The Red Lion Inn

Stockbridge

Raphael

includes taxes & fees

23 Jul - 24 Jul

Shaker Mill Inn

West Stockbridge

Mervin

includes taxes & fees

8 Jul - 9 Jul

Becket Motel

Becket

Paul

includes taxes & fees

6 Jul - 7 Jul

Berkshire Mountain Lodge

Pittsfield

Andrew

includes taxes & fees

3 Aug - 4 Aug

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

Pittsfield

Matthew

includes taxes & fees

8 Jul - 9 Jul

The Little Lion

Great Barrington

Mia

includes taxes & fees

13 Jul - 14 Jul

Big farmhouse in the foothills of the Berkshires

Russell

Will G.

includes taxes & fees

12 Jul - 13 Jul

Howard Johnson by Wyndham Lenox

Lenox

robert

includes taxes & fees

7 Jul - 8 Jul

Monument Mountain Motel

Great Barrington

Yekaterina

includes taxes & fees

2 Aug - 3 Aug

Quality Inn Lee - Lenox South

Lee

Cheri

includes taxes & fees

7 Jul - 8 Jul

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Top Monterey Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"Breakfast was great! We were caught off guard by the parking lot renovation but the free valet parking made up for it. Staff was very friendly! "

Berkshires Untold

8/10 Good

"The decor of the room was very nice. It was a very clean and pleasant room with quality bedding and towels. The heat and humidity did not make it possible to enjoy the patio. I probably would not have used it, if our weather had permitted, because there was no umbrella or covering to protect you from the sun. The grounds need a little more lawn care and landscaping. Most importantly, travelers need to know that no elevator is provided to reach the second story guest rooms. This information should be more transparent."

Quality Inn Great Barrington

10/10 Excellent

"I booked the stay at Quality Inn without knowing what to expect. Getting to the hotel was easy. The location was perfect with mountains all around. Comfortable bed and just right amenities made the stay enjoyable. The breakfast sitting area was separate from the hotel and had a cottage feel, enjoyed having breakfast. Exploring the town of Great Barrington was easy as everything was walking distance. Quality Inn is right next to Town Hall. Had a perfect view of the Strawberry moon sitting on the bench outside of the town hall. It was fun to see through the window of the Great Barrington fm radio station and chatting with the DJ hen he stepped out. A must to stop at SoCo ice-cream shop delicious cold treats. People are very friendly. The Pizza at The Great Barrington Pizza house was delicious. Walking around we could feel the history that has transpired, small town vibe, the architecture. Do not miss going to Great Barrington Farmers market, it is a co-op market and Guido's family owned super market."

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

8/10 Good

"We had a lovely, one night stay here. I went with my adult son and his girlfriend to see Paul Simon at Tanglewood (which turned out to be an amazing show!) The front desk staff at the resort were friendly and accommodating; they let us use the amenities early before we could check in, which was GREAT! We hung around the outdoor pool, met a lot of nice people, and had a blast. Our suite was great. Parking was easy and plentiful and we had 2 bedrooms and each had it's own bathroom for full privacy. Full kitchen with fridge and freezer, a little living room and a nice outdoor deck overlooking the woods and a brook. It was clean, comfortable, and we had a wonderful stay. There is a grocery store just a few miles down the street for everything you need and Lenox is about 10-15 minutes away. We even saw a bear in the parking lot and he went out back in the woods where our porch was. I've never had a bear sighting. It was awesome! The only thing I can comment is the windows in the front bedroom were pretty dirty. It would have been nice it they were cleaned up. Honestly it didn't make or break our trip, just a business owner myself, I always like the feedback. But all in all, I would definitely recommend and definitely stay there again."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Loved this place. It was a bit dated aesthetically, but the charm outweighed that. Beds are comfortable. The setting on the lake is beautiful and its size of the hotel is lovely. Staff and guests were delightful. In retrospect, I wish I’d paid more for a lakefront room — it would’ve been worth it. Hotel is centrally located and it’s easy to get everywhere. Only negative was that there was no recycling."

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

10/10 Excellent

"Wonderful, clean and new hotel in great location between Lenox and Pittsfield. Room was lovely, bed comfortable, and breakfast offered everything you would expect. Staff was friendly and helpful. We were delighted to find this place and will definitely return next time we come to the Berkshires."

Find out more about Monterey

Monterey Chalets information

Number of reviews	10,969
Accommodation	4 Chalets
Lowest Price	£47
Highest Price	£193

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Monterey

FairBridge Inn Express

Locust Tree Bed and Breakfast LLC

Berkshire Lake Lodge

The Yankee Inn

Best Western Plus Berkshire Hills Inn & Suites

Wilder House Berkshires

Blackberry River Inn

Berkshire Inn

Berkshire Travel Lodge

Quality Inn Great Barrington

The Red Lion Inn

Shaker Mill Inn

Becket Motel

Berkshire Mountain Lodge

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

The Little Lion

Big farmhouse in the foothills of the Berkshires

Howard Johnson by Wyndham Lenox

Monument Mountain Motel

Quality Inn Lee - Lenox South

Find holiday rentals that suit your style

Top Monterey Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Monterey

Monterey Chalets information

Explore a world of travel with Expedia