A person snowboarding down a snowy slope.

The Berkshires Vacation Rentals

  • 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

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for The Berkshires vacation rentals

Exterior

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,269 reviews)
"Excellent stay!!!!"
United States
Susan J
The price is ￥12,183
￥17,154 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge
Indoor pool

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,841 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is ￥12,752
￥15,985 total
includes taxes & fees
Dec 6 - Dec 7
Vacation Village in the Berkshires
A hot tub with a string of lights above it, set against a dark night sky.

3. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥25,427
￥59,428 total
includes taxes & fees
Nov 13 - Nov 14
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

4. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is ￥12,142
￥18,350 total
includes taxes & fees
Nov 21 - Nov 22
Cozy 1-bedroom studio in serene Great Barrington with AC
A wooden fence, a potted plant, a wooden bench, and a small garden area with a stone pathway.

5. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
The price is ￥22,856
￥27,657 total
includes taxes & fees
Dec 1 - Dec 2
Cozy Camper tucked into the woods
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

6. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is ￥23,141
￥56,698 total
includes taxes & fees
Nov 15 - Nov 16
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

7. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is ￥9,746
￥45,330 total
includes taxes & fees
Nov 26 - Nov 27
Real Estate: Therapy - Lake, Laundry, Love it
A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

8. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (14 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is ￥15,386
￥33,784 total
includes taxes & fees
Nov 15 - Nov 16
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A bedroom with a large bed, a brick wall, a window with curtains, and a wall clock.

9. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"Great place, everything was so easy!!"
United States
Dana
The price is ￥15,386
￥33,784 total
includes taxes & fees
Nov 15 - Nov 16
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

10. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (19 reviews)
"It's super well located, with a view of the hills from the picture window. Everything is comfortable, everything worked, and host's communication was excellent. Highly recommended."
United States
David
The price is ￥17,095
￥36,049 total
includes taxes & fees
Nov 16 - Nov 17
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

11. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (41 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is ￥31,203
￥69,834 total
includes taxes & fees
Nov 15 - Nov 16
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A sandy beach with a lake and forest in the background.

12. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is ￥33,392
￥51,933 total
includes taxes & fees
Nov 15 - Nov 16
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

13. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is ￥31,744
￥47,868 total
includes taxes & fees
Dec 13 - Dec 14
Home in Great Barrington
A cozy living room with a large window, wooden walls, and a television.

14. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is ￥15,386
￥33,784 total
includes taxes & fees
Nov 15 - Nov 16
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

15. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
The price is ￥15,386
￥33,784 total
includes taxes & fees
Nov 15 - Nov 16
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A dining area with a wooden table, chairs, and a ceiling fan.

16. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is ￥32,141
￥47,780 total
includes taxes & fees
Nov 25 - Nov 26
Leaf-Peeper Paradise in the Berkshires
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

17. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (35 reviews)
"Very smooth process for check in and directions. Well provisioned, super clean rooms. Really enjoyed learning about Dalton. And so many sights nearby we love!"
United States
Marcia O.
The price is ￥17,974
￥47,739 total
includes taxes & fees
Nov 17 - Nov 18
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

18. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is ￥27,960
￥46,222 total
includes taxes & fees
Nov 14 - Nov 15
Sweet Cozy Victorian in Housatonic. Close to everything.
A living room with a blue sofa, a TV on a stand, a small table with a lamp, and a window with curtains.

19. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (13 reviews)
"Great location, very clean, included washer dryer, picnic area by river, large parking space."
United States
Douglas
The price is ￥23,886
￥47,762 total
includes taxes & fees
Nov 16 - Nov 17
Downtown | Waterfront | Walk to Shops
Work desk

20. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.2 out of 10, Wonderful, (23 reviews)
"Perfect check in process, spotlessly clean, gorgeous property, and I wish I had had enough time to relax by the water. Best experience I've had, and I will definitely stay there again."
United States
Andrea
The price is ￥21,903
￥46,278 total
includes taxes & fees
Nov 15 - Nov 16
2-Bdr Apt In Town, By the Water
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Breakfast was h asic everything else was perfect"
paul 2-night trip
Posted 1 hour ago
The Yankee Inn

Find out more about The Berkshires

Search for holiday rentals in The Berkshires on Expedia! You can easily find your home rentals, villas, holiday apartments in The Berkshires using one of the methods below:

  • View our selection of featured holiday rentals in The Berkshires
  • Use the map to find apartments and other holiday homes in the The Berkshires neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in The Berkshires while they last

Look no further and take a look at our great range of rental properties in The Berkshires!

Explore a world of travel with Expedia