A historic stone building with a yellow roof, surrounded by a white fence and lush green grass.

Berkshire County Holiday 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

Our top choices for Berkshire County holiday rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,143 reviews)
"Clean & comfortable stay"
United States
Robert
The price is AU$155
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,637 reviews)
"Great all around stay and lots for the kids to do"
United States
Sarah
The price is AU$164
includes taxes & fees
15 Sept - 16 Sept
Vacation Village in the Berkshires
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

3. 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, (31 reviews)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
The price is AU$552
includes taxes & fees
19 Sept - 20 Sept
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A snow-covered outdoor area with a fire pit, tables, and chairs.

4. 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 AU$316
includes taxes & fees
14 Sept - 15 Sept
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

5. 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, (39 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 AU$596
includes taxes & fees
15 Sept - 16 Sept
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

6. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (40 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveller
The price is AU$1,164
includes taxes & fees
28 Sept - 29 Sept
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

7. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (25 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 AU$435
includes taxes & fees
21 Sept - 22 Sept
Riverside Retreat in the Berkshires
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

8. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is AU$774
includes taxes & fees
14 Sept - 15 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

9. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house with great amenities in a convenient location. We loved the open concept that provided a great space for cooking, hanging out and playing games together while enjoying a beautiful view. The gameroom was so much fun, and we’d love to visit again when the sauna is finished. Our family of 6 and family dog loved it!"
United States
Rebecca K.
The price is AU$1,819
includes taxes & fees
14 Sept - 15 Sept
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A sandy beach with a lake and forest in the background.

10. 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, (4 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 AU$481
includes taxes & fees
14 Sept - 15 Sept
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

11. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AU$1,570
includes taxes & fees
15 Sept - 16 Sept
Hancock Village Inn Near Jiminy Peak
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.

12. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$517
includes taxes & fees
14 Sept - 15 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

13. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is AU$830
includes taxes & fees
15 Sept - 16 Sept
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A hot tub with a string of lights above it, set against a dark night sky.

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$538
includes taxes & fees
27 Sept - 28 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

15. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AU$428
includes taxes & fees
15 Sept - 16 Sept
Home in Great Barrington
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

16. The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The price is AU$678
includes taxes & fees
7 Oct - 8 Oct
The Greylock Cabin
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is AU$435
includes taxes & fees
25 Sept - 26 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.

18. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (19 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is AU$372
includes taxes & fees
14 Sept - 15 Sept
New Studio In Town, By the Water
A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

19. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (15 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
The price is AU$387
includes taxes & fees
14 Sept - 15 Sept
Penthouse Apartment on Park Street
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

20. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (44 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AU$602
includes taxes & fees
27 Sept - 28 Sept
Cheerful 3-bedroom cottage with woodstove
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 Berkshire County Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Loved the pond trail! What a nice shift after a long day on the road."
Deborah 1-night trip
Posted 1 hour ago
The Yankee Inn

Find out more about Berkshire County

Everything you need to know about Berkshire County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Berkshire County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Berkshire County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Berkshire County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Berkshire County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Berkshire County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Berkshire County holiday rentals we have chosen for you start as low as AU$155 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Berkshire County rentals

At Expedia, we put the best Berkshire County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Berkshire County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Berkshire County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Berkshire County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.