Holiday Homes in The Berkshires

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in The Berkshires

Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is AU$1,117
includes taxes & fees
12 Aug - 13 Aug
Spacious 5-bedroom house in charming Lee with WiFi
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Situated in a grassy yard, this charming house features a sloped roof, chimney, and a small window.

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

9.8 out of 10, Exceptional, (17)
"We had a wonderful time, the property is lovely and the house is delightful."
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Contemporary Berkshire Home with Views of Taconic Golf Course
Relax in this spacious living room with a high ceiling, featuring a sofa, armchair, and coffee table.

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (5)
Contemporary Berkshire Home with Views of Taconic Golf Course
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Experience the perfect blend of traditional and contemporary style in this inviting space, featuring a plush sofa, wooden coffee table, and modern kitchen.

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (45)
"We went as a family to get away from the city life for the weekend. We have no complaints except that it could’ve been a bit cleaner in the sense that there were many cobwebs. Nonetheless we rlly enjoyed our weekend in Great Barrington "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Charming Berkshires Retreat – Minutes to Williamstown
Enjoy cooking and dining with a large dining table and modern kitchen amenities.

Charming Berkshires Retreat – Minutes to Williamstown

6.0 out of 10, (2)
"This was the perfect little spot for our family to stop and stay on our way to dropping our daughter at camp and enjoy Williamstown. Our hike at the Clark Institute was a highlight along with the proximity to downtown’s great restaurants.We were talking about how gorgeous it must be in the fall… when it must be even more scenic and amazing."
Charming Berkshires Retreat – Minutes to Williamstown
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Escape to a serene lakeside retreat surrounded by lush greenery and vibrant flowers.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (14)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
19th c. Barn in the Berkshires
Relax in this spacious living room with a high ceiling, leather sofa, and wooden coffee table.

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (90)
"We planned to stay at this property in order to ski at Jiminy peak, and it was perfect, not a long drive at all. The barn stays very warm with the individual heaters as well as the wood stove in the middle of the main room. The kitchen was equipped with everything you need, they even had coffee and sugar! .. Communication with the hosts was seamless. We lost power due to a winter storm, the entire area did, and that wood stove worked its magic. The property owners made sure we were alright...
19th c. Barn in the Berkshires
Art House! Spacious Getaway By Mass Moca
Meetings and gatherings take place in this elegantly designed room with a long table and comfortable seating.

Art House! Spacious Getaway By Mass Moca

10.0 out of 10, Exceptional, (11)
"We had a great girls weekend e joying local trails, MassMOCA, local restaurants and this very clean, spacious house! Location is walkable to the museum and down town and we enjoyed a soak in the tub after a day of hiking in local conservation areas! "
Art House! Spacious Getaway By Mass Moca
Poolside Luxe at Long Pond
Exterior

Poolside Luxe at Long Pond

Poolside Luxe at Long Pond
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Relax in a serene outdoor space with Adirondack chairs and a shaded gazebo.

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (9)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Spectacular views and close to Great Barrington.
Relax in this inviting living area with a high ceiling, brick fireplace, and expansive windows offering views of the surrounding landscape.

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay in Great Barrington for the long holiday weekend. The house is very comfortable, super clean, and the property is lovely. We were able to cool off in the pool and enjoy time with family. 10/10!"
Spectacular views and close to Great Barrington.
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Relax in this serene space with a comfortable chair and a staircase leading to an upper level.

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (44)
"The home is very nice and cozy. It really felt like a comfy home."
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
North Getaway Cottage
Stunning two-story house with a central entrance and lush green surroundings.

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is AU$697
includes taxes & fees
7 Aug - 8 Aug
North Getaway Cottage
Secluded Family Home in Serene Stockbridge Woods
Enjoy meals with family and friends in this spacious dining area with a long table and comfortable seating for four.

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (21)
"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."
Secluded Family Home in Serene Stockbridge Woods
Charming 3-bedroom farmhouse in Lenox
Relax on the outdoor deck with Adirondack chairs, perfect for a quiet moment or al fresco dining.

Charming 3-bedroom farmhouse in Lenox

10.0 out of 10, Exceptional, (1)
"House is comfortable and spacious, with a well-supplied kitchen. Hosts had thought of everything we might need. A/C was very helpful in the heat! Perfect location for exploring the Berkshires, and a fairly easy walk into town."
Charming 3-bedroom farmhouse in Lenox
Country Living just minutes from Everything!
Enjoy cooking in this well-lit kitchen with a stainless steel refrigerator, oven, and coffee maker.

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (28)
"Jandie's was the absolute best rental house we have ever stayed at. The house was clean and well kept, everything felt brand new. The set up was great, open kitchen, dining room and living room and made entertaining very easy. The kids had their own room and enjoyed spending time together in their own space. Julie was a pleasure to work with and accommodated us in anyway she could, from beginning to end. She even made us homemade delicious treats. We would highly recommend Jandie's and we...
Country Living just minutes from Everything!
Family Ski House at Catamount !
Relax in this stylish living room with a high ceiling, large windows, and a comfortable sofa.

Family Ski House at Catamount !

10.0 out of 10, Exceptional, (2)
"Proximity to Catamount was ideal. Short drive to Great Barrington. The place was nice and sunny, and very comfortable. The mud room was fantastic for stowing gear and dressing in ski clothes. Overall, a very nice property. "
Family Ski House at Catamount !
Sophisticated Lenox Retreat by Evergreen Home
Enjoy the serene view from the front deck, surrounded by lush trees and a beautifully manicured lawn.

Sophisticated Lenox Retreat by Evergreen Home

9.8 out of 10, Exceptional, (9)
"Very quaint location, clean property, and great place to stay"
Sophisticated Lenox Retreat by Evergreen Home
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Relax in the backyard patio area with a table, chairs, and cushioned benches under a pergola.

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Deluxe Queen Room with 2 Queen Beds
Guest rooms lead to a covered walkway with a tiled floor.

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (2)
"The chemical smell in the room was overwhelming. There was no personal contact We called the number provided and was told We would get a full refund."
The price is AU$209
includes taxes & fees
1 Sept - 2 Sept
Deluxe Queen Room with 2 Queen Beds
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free