A person snowboarding down a snowy slope.

Search The Berkshires Guest Houses

  • 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
25 Sept - 27 Sept
In two weeks
2 Oct - 4 Oct
In one month
16 Oct - 18 Oct
In two months
13 Nov - 15 Nov

Our top choices for The Berkshires guest houses

A large white house with a prominent tower, surrounded by lush greenery and a well-maintained lawn.

1. Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
7.8 out of 10, Good, (59 reviews)
"Although the property was vintage, the rooms were clean and staff were very helpful and fun to be around. Parking and breakfast were included and the location was excellent."
United States
Barbara
The price is AU$208
includes taxes & fees
17 Sept - 18 Sept
Hideaway Inn Lenox
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

2. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (410 reviews)
"Large, clean, comfortable suite."
United States
Rena
The price is AU$154
includes taxes & fees
8 Oct - 9 Oct
The Central Downtown Inn & Suites
A living room with a fireplace, two sofas, and four black side tables.

3. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (38 reviews)
"Room 6 was much larger than expected! We arrived after hours and it was very easy to find our room."
United States
Katrina
The price is AU$259
includes taxes & fees
20 Sept - 21 Sept
The Revival House
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

4. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (294 reviews)
"A cute, quiet getaway close to the Berkshire mountains!"
United States
Maya H.
The price is AU$296
includes taxes & fees
17 Sept - 18 Sept
Berkshire Village Carriage House - Super Private!!
A dining area with wooden tables and chairs, large windows with white frames, and wall-mounted light fixtures.

5. Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (173 reviews)
"Disappointed. Would not stay there again. Only plus was breakfast, which was excellent."
United States
Richard T
The price is AU$341
includes taxes & fees
23 Sept - 24 Sept
Cornwall Inn and Lodge
A stone cottage with a turquoise door, a sign reading 'Windy Top Cottage,' and flower boxes on the windows.

6. A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
10.0 out of 10, Exceptional, (113 reviews)
"We loved our stay! The cottage was adorable!"
United States
Kristen S.
The price is AU$354
includes taxes & fees
20 Sept - 21 Sept
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
A two-story house with a porch, a balcony, and a chimney.

7. Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (150 reviews)
"Lovely Victorian house on a quiet street. Only a few blocks from the center of the town of Shelburne Falls, which is a charming New England town with a lovely river and a beautiful "bridge of flowers.""
United States
steven
The price is AU$227
includes taxes & fees
21 Sept - 22 Sept
Blooming Inn
A two-story house with a stone staircase leading to a wooden front door.

8. The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.2 out of 10, Wonderful, (74 reviews)
"For booking an overnight stay at the last minute, this place hit the jackpot, and BEYOND EXCEEDED my expectations! The owner was so sweet, and if I ever pass through Wilmington again, I'd definitely stay there again!!!"
United States
Chandra
The price is AU$316
includes taxes & fees
14 Oct - 15 Oct
The Inn At Quail Run
A modern kitchen with a dining area, a large window, and a view of the garden.

9. 9 Academy

9 Academy
4.0 star property
Salisbury
9.4 out of 10, Exceptional, (14 reviews)
"Extremely clean and the rooms are beautifully decorated with warm minimal decor. We will definitely be back!"
United States
Gina
The price is AU$947
includes taxes & fees
23 Sept - 24 Sept
9 Academy
A wooden deck with two black wicker chairs and a small round table with a white vase.

10. In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony
Shelburne Falls
10.0 out of 10, Exceptional, (131 reviews)
"It's a great place to stay! Bed is comfortable. Large room, nicely furnished. Would be glad to stay here again!"
United States
Jim E.
The price is AU$372
includes taxes & fees
12 Oct - 13 Oct
In town, newly remodeled studio with private balcony

11. Cooper Hill Inn

Cooper Hill Inn
2.0 star property
West Dover
8.8 out of 10, Excellent, (8 reviews)
"Very convenient to Mount Snow and we loved the plentiful cozy places to sit and read or interact with other guests. The bed was comfortable, and the shared kitchen space was very well stocked and clean. We will definitely stay again!"
United States
Rosa
The price is AU$316
includes taxes & fees
17 Sept - 18 Sept
Cooper Hill Inn
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
"Excellent location. Excellent adjacent restaurant "Door Prize". Will definitely stay again"
Dolores 3-night trip
Posted 17 hours ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about The Berkshires

The Berkshires Guest Houses information

Number of reviews
1,405
Accommodation
9 Guest Houses
Lowest Price
AU$154
Highest Price
AU$947

Explore a world of travel with Expedia