A person snowboarding down a snowy slope.

Search Best Resorts in The Berkshires

  • 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 prices for these dates

Next weekend
24 July - 26 July
In two weeks
31 July - 2 Aug
In one month
14 Aug - 16 Aug
In two months
11 Sept - 13 Sept

Our top choices for The Berkshires resorts

Interior

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Pittsfield
10.0 out of 10, Exceptional, (1 review)
"We loved everything about this place! It was quiet, centrally located, and everyone was friendly and helpful. We will stay here again for sure!"
United States
Christine B.
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Exterior

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property
3.0 star property
West Dover
8.6 out of 10, Excellent, (291 reviews)
"Excellent stay, looking forward to visiting again!"
United States
Jordyn C
The price is AU$265
includes taxes & fees
20 July - 21 July
Grand Summit Resort, A Vail Resorts Property
Dining

Deluxe King Room w/pull-out love seat and fireplace

Deluxe King Room w/pull-out love seat and fireplace
Dover
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfect"
United States
James R.
The price is AU$625
includes taxes & fees
15 July - 16 July
Deluxe King Room w/pull-out love seat and fireplace
Exterior

Deluxe King, kitchenette, fireplace

Deluxe King, kitchenette, fireplace
West Dover
10.0 out of 10, Exceptional, (4 reviews)
"End of season special. Perfect size, fireplace was great on a cold rainy night. Last night restaurant was open for a few weeks."
United States
john L.
The price is AU$661
includes taxes & fees
29 July - 30 July
Deluxe King, kitchenette, fireplace
Interior

Deluxe King Room w/fireplace and separate entrance

Deluxe King Room w/fireplace and separate entrance
West Dover
10.0 out of 10, Exceptional, (4 reviews)
"We thoroughly enjoyed our one-night stay. Our room was cozy and all the staff were wonderful."
United States
Charles B.
The price is AU$625
includes taxes & fees
15 July - 16 July
Deluxe King Room w/fireplace and separate entrance
Exterior

Deluxe King, Living Room w/sofa bed, bunk bed & fireplace

Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
Dover
9.4 out of 10, Exceptional, (6 reviews)
"This is a beautiful, large suite in a quaint Vermont town. There are two main rooms: a bedroom with a king bed and a bunk bed, and a separate living room with a fireplace. The main inn also has lounge areas open to guests all night, and is a perfect stay for both families and couples. "
United States
Olivia
The price is AU$661
includes taxes & fees
22 July - 23 July
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
1 bedroom, iron/ironing board, WiFi

Deluxe 2xQueen- 2nd floor in Historic Inn

Deluxe 2xQueen- 2nd floor in Historic Inn
West Dover
10.0 out of 10, Exceptional, (5 reviews)
"Everything was just fantastic! Everyone was friendly and accommodating. Owners were so nice! Property is amazing and a great location to Mount Snow. Can not go wrong with this spot."
United States
Brendan M.
The price is AU$565
includes taxes & fees
15 July - 16 July
Deluxe 2xQueen- 2nd floor in Historic Inn
1 bedroom, iron/ironing board, WiFi

Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance

Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
Dover
10.0 out of 10, Exceptional, (2 reviews)
"The place was clean, cozy and comfortable. The whole estate is beautiful."
United States
Mike T.
The price is AU$661
includes taxes & fees
22 July - 23 July
Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
1 bedroom, iron/ironing board, WiFi

Deluxe 2xQueen & fireplace

Deluxe 2xQueen & fireplace
Dover
10.0 out of 10, Exceptional, (1 review)
"Beautiful Inn however, the fridge should be lifted off the floor. It’s too low. A small broom and dust pan would be nice to sweep up the dirt that treks in from the dirt parking lot and walk ways. Upgrade full size beds to at least two Queen size beds."
United States
Christina R.
The price is AU$565
includes taxes & fees
20 July - 21 July
Deluxe 2xQueen & fireplace
Exterior

King with Bunk Bed- 2nd floor in Historic Inn

King with Bunk Bed- 2nd floor in Historic Inn
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Very well apportioned room. Super clean and comfortable. Restaurant was delicious. Bartender is cool to chat with."
United States
Forrest W.
The price is AU$625
includes taxes & fees
16 July - 17 July
King with Bunk Bed- 2nd floor in Historic Inn
1 bedroom, iron/ironing board, WiFi

Deluxe 2xQueen in Historic Inn

Deluxe 2xQueen in Historic Inn
West Dover
8.0 out of 10, Very good, (1 review)
The price is AU$561
includes taxes & fees
22 July - 23 July
Deluxe 2xQueen in Historic Inn
Exterior

Deluxe King, Living Room w/sofa bed & fireplace

Deluxe King, Living Room w/sofa bed & fireplace
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Had a really nice time - the place was lovely. They had some on property activities and were very close to the mountain. We had a great time and would definitely stay here again if back in the area!"
United States
Taylor G.
The price is AU$661
includes taxes & fees
12 Aug - 13 Aug
Deluxe King, Living Room w/sofa bed & fireplace
Exterior

Deluxe King Suite, Living Room w/sofa bed & fireplace

Deluxe King Suite, Living Room w/sofa bed & fireplace
West Dover
10.0 out of 10, Exceptional, (1 review)
"My husband and I really enjoyed the accommodations. Great location with tons do do nearby. The place was so cozy and inviting. Would definitely stay again"
United States
Megan M.
The price is AU$661
includes taxes & fees
12 Aug - 13 Aug
Deluxe King Suite, Living Room w/sofa bed & fireplace
Interior

Deluxe Queen Suite with pull-out love seat, private entrance

Deluxe Queen Suite with pull-out love seat, private entrance
Dover
The price is AU$561
includes taxes & fees
12 Aug - 13 Aug
Deluxe Queen Suite with pull-out love seat, private entrance
Exterior

Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
The price is AU$621
includes taxes & fees
12 Aug - 13 Aug
Deluxe King - 2nd floor in Historic Inn
Exterior

Luxury King w/balcony, accessible

Luxury King w/balcony, accessible
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"My husband and I had a wonderful time at the Inn . our room was beautiful and we had two delicious meals in the restaurant I would definitely recommend this Inn to anyone traveling in southern Vermont."
United States
Kimberley B.
The price is AU$621
includes taxes & fees
12 Aug - 13 Aug
Luxury King w/balcony, accessible
Interior

Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance

Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
Dover
9.8 out of 10, Exceptional, (7 reviews)
"My husband and I stayed here so we could ride Mt Snow for a few days. The place is wonderful! All staff is incredibly helpful and friendly, the food and cocktails in their restaurant are phenomenal, the landscape and accommodation are beautiful. We will definitely be back."
United States
Sydney W.
The price is AU$768
includes taxes & fees
19 July - 20 July
Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
Exterior

Luxury King Suite, Living Room w/sofa bed and jacuzzi tub

Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Such a quaint, beautiful Spot. It’s uniqueness, historic feel and common area was very warming. Personnel was very friendly and attentive"
United States
Jessica
The price is AU$621
includes taxes & fees
12 Aug - 13 Aug
Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
Exterior

Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
The price is AU$621
includes taxes & fees
12 Aug - 13 Aug
Deluxe King - 2nd floor in Historic Inn
1 bedroom, iron/ironing board, WiFi

Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths

Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
West Dover
8.0 out of 10, Very good, (1 review)
"The inn and grounds were wonderful. Great food at the Sawmill. Wonderful area to explore leading to an all around wonderful time."
United States
Craig C.
The price is AU$628
includes taxes & fees
15 July - 16 July
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top The Berkshires Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Property and hotel was very clean. The staff was pleasant and helpful."
Michael 1-night trip
Posted 10 hours ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about The Berkshires

The Berkshires Resort information

Number of reviews
335
Accommodation
30 Resort
Lowest Price
AU$265
Highest Price
AU$768

Explore a world of travel with Expedia