The Best The Berkshires, MA Chalets from $341

A person snowboarding down a snowy slope.

Bundle & Save
Get more, spend less whenever you see Bundle & Save deals
OneKeyCash
Earn OneKeyCash on all your eligible bookings
Upfront pricing
We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for The Berkshires chalets

A wooden building with a thatched roof and a wooden deck leading to it.

1. Vikings Villages Resort - Double Bed Room

Guilford

$336 nightly

Oct 13 - Oct 14

Total with taxes and fees

A view of a forested area with a bench in the foreground.

2. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Charlemont

Georgia P.

$1,173 nightly

Nov 2 - Nov 3

Total with taxes and fees

A large, single-story house with a symmetrical roof and a central chimney, surrounded by a well-maintained lawn and dense forest with autumn foliage.

3. Sleeps 16 Chalet: Pool, Hot Tub, Game Rooms. Pet-Friendly.

Cropseyville

Patrick H.

$1,619 nightly

Nov 4 - Nov 5

Total with taxes and fees

A two-story wooden house with a stone retaining wall, a covered porch, and a small shed.

4. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Dover

Brian S.

$407 nightly

Oct 13 - Oct 14

Total with taxes and fees

5. NEW Private Chalet - 4 mins to Mt Snow

Dover

Mark C.

$589 nightly

Oct 13 - Oct 14

Total with taxes and fees

A two-story house with a large deck and a covered porch, surrounded by trees and a grassy yard.

6. Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

Dover

Andrew B.

$476 nightly

Oct 27 - Oct 28

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cabins

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Top The Berkshires Hotel Reviews

Hotel On North

10/10 Excellent

"Cool property. Very clean. Every room is unique, which makes it fun."

The Red Lion Inn

8/10 Good

"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."

Berkshires Untold

8/10 Good

"First this is a gorgeous property, the outdoor areas are wonderful, with comfy furniture, flowers and fire pits. The main area is an intimate restaurant and bar, with a seating area with books and plants. We enjoyed drinks and dinner there and it was excellent, particularly with the sunset and fire pit to begin our evening, Absolutely lovely! Upon checking in, we were assigned a “premium” room, which sounded great, however it turned out to be on the second floor, at the end of a very long outside corridor, parking and lobby quite distant. They have no elevator. We did lug our bags and a cooler to the room, which was lovely, but we knew we would be much more comfortable on the first floor closer to the lobby, as we are somewhat older. We asked to be moved, and we accommodated, found the room the same, but lacking the coffee service and luggage rack. We were brought a luggage rack, and complimentary coffee was available in the lobby in the morning, but it seemed odd that those would be considered premium in such a nice place. The star of the place is the beautiful outdoor space, and restaurant, we just loved that!"

Quality Inn Great Barrington

8/10 Good

"First, this is an absolutely gorgeous place! The outside areas are beautiful with comfy furniture, flowers and fire pits. Inside is a small intimate restaurant and bar, plus sitting area. With books and plants, very nice. We had dinner there which was excellent, and loved cocktails and sunset outside by the fire pits. When we checked in, we were assigned one of their premium rooms, which sounded great. However, it was on the second floor, at the very end of a long outside corridor, accessible only by stairs near the lobby. There is no elevator. We did go to the room, lugging our bags and a cooler. Unpleasant, as we are somewhat older. We concluded that we did not want to be that far from the main area, so asked to be moved, and were accommodated. We found the new room the same, but lacking a luggage rack and a coffee service (those were only available in the premium rooms at the end of the long corridor). We were given a luggage rack, and complimentary coffee was available in the restaurant in the morning, but it seemed odd that those were considered premium in such a nice place. Otherwise we loved the hotel, room was very nice with a comfortable bed and a very updated bath with a walk in shower. The real star of the hotel is the lobby restaurant and outdoor space - that was just perfect!"

Find out more about The Berkshires

The Berkshires Chalets information

Number of reviews	46
Accommodation	2 Chalets
Lowest Price	$341
Highest Price	$1,797

Explore a world of travel with Expedia

Things to do in Western Massachusetts

Room 1

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for The Berkshires chalets

1. Vikings Villages Resort - Double Bed Room

2. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

3. Sleeps 16 Chalet: Pool, Hot Tub, Game Rooms. Pet-Friendly.

4. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

5. NEW Private Chalet - 4 mins to Mt Snow

6. Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

Find vacation rentals that suit your style

Top The Berkshires Hotel Reviews

Hotel On North

The Cornell Inn, Lenox & The Berkshires

The Red Lion Inn

Berkshire Mountain Lodge

Vacation Village in the Berkshires

Hampton Inn & Suites Berkshires-Lenox

Berkshires Untold

Quality Inn Great Barrington

FairBridge Inn Express

Find out more about The Berkshires

The Berkshires Chalets information

Explore a world of travel with Expedia