Holiday Rentals in Berkshire County

    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

Featured Holiday Rentals in Berkshire County

Berkshire Village Carriage House - Super Private!!
Enjoy cooking in this well-equipped kitchen with a central island, sink, and ample seating for two.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (253)
"One of the best properties i've ever stayed at "
The price is €255
includes taxes & fees
31 Jul - 1 Aug
Berkshire Village Carriage House - Super Private!!
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 €392
includes taxes & fees
29 Jul - 30 Jul
North Getaway Cottage
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a window with a view.

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is €528
includes taxes & fees
4 Aug - 5 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Home in Great Barrington
Enjoy cooking in this well-lit kitchen with a large window offering a view of the outdoors.

Home in Great Barrington

9.8 out of 10, Exceptional, (21)
"Our family had a wonderful experience and stay. "
Home in Great Barrington
Experience Timeless Elegance in The Edith Wharton Room!
Cozy retreat with a large bed, dresser, desk, and TV.

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Enjoy al fresco dining and socializing on this tranquil outdoor deck, complete with a barbecue grill and comfortable seating.

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay here. Location was excellent. Very peaceful and quiet. The house was clean and had everything you needed. Would come again!"
The price is €346
includes taxes & fees
28 Jul - 29 Jul
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Comfortable Berkshires retreat on mtn resort, SISO
Relax by the pool surrounded by lush views and shaded lounge areas.

Comfortable Berkshires retreat on mtn resort, SISO

9.6 out of 10, Exceptional, (4)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is €436
includes taxes & fees
29 Jul - 30 Jul
Comfortable Berkshires retreat on mtn resort, SISO
NEW RENO Historic Creamery in Berkshires w/hot tub
Relax in a spacious outdoor living area with a comfortable sofa set and sheltered seating options.

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (1)
"Absolutely AMAZING house beautiful inside and out the features are absolutely amazing!! Carl the host is super nice. Definitely 100% recommend staying here! "
The price is €605
includes taxes & fees
24 Aug - 25 Aug
NEW RENO Historic Creamery in Berkshires w/hot tub
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Cozy living room with a comfortable sofa, throw blanket, and fireplace.

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

9.8 out of 10, Exceptional, (7)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
The price is €415
includes taxes & fees
6 Aug - 7 Aug
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Cheerful 3-bedroom cottage with woodstove
Relax in a serene outdoor space surrounded by lush greenery, featuring a wicker sofa set and a coffee table.

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (38)
"The property was centrally located for skiing, and was a comfortable stay."
Cheerful 3-bedroom cottage with woodstove
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Relax by the large pool in our outdoor space.

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

9.8 out of 10, Exceptional, (70)
"We had a wonderful stay, thank you! "
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.
Relax on the covered porch with two comfortable rocking chairs overlooking a serene grassy area surrounded by trees.

Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.

10.0 out of 10, Exceptional, (3)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
The price is €530
includes taxes & fees
13 Aug - 14 Aug
Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.
Great Barrington Get Away
Enjoy cooking in this kitchen with stainless steel appliances, a large window offering a view of the outdoors, and a convenient trash can.

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is €584
includes taxes & fees
4 Aug - 5 Aug
Great Barrington Get Away
Hancock Village Inn at Jiminy Peak
Charming two-story house with a historic facade, featuring a prominent address and star symbol, set amidst a serene winter landscape.

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is €904
includes taxes & fees
28 Jul - 29 Jul
Hancock Village Inn at Jiminy Peak
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 €723
includes taxes & fees
31 Jul - 1 Aug
Spacious 5-bedroom house in charming Lee with WiFi
Cozy Carriage House room with a double bed and private balcony
Cozy retreat with a neatly made bed, bedside table, and elegant mirror.

Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Historic Susan B. Anthony Room - Cozy & Charming Stay
Step outside to a serene outdoor space with a deck, Adirondack chairs, and a charming playhouse.

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Elegant Carriage House room with a queen bed and private patio.
Cozy retreat with a large bed, dresser, and table, set amidst classic floral wallpaper and a decorative ceiling.

Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Relax in a stylish room with a comfortable bed, a small table, and a dresser, plus a large mirror and artwork on the wall.

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Relax in a serene bedroom with a tufted headboard, desk, and dresser, perfect for work and rest.

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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

Top Berkshire County Hotel Reviews

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

10/10 Excellent
"The hotel was very unique as there was art spaces in the lobby. Liked that the room had lvp flooring. "
stephen 2-night trip
Posted 19 hours ago
Hotel Downstreet, Ascend Hotel Collection