Vacation Rentals in Berkshire County

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Top cities in Berkshire County

A large white house with multiple chimneys, surrounded by lush greenery and trees.
Vacation Rentals

Lenox

Lenox

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 Berkshire County vacation rentals

Exterior

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,268 reviews)
"Excellent stay!!!!"
United States
Susan J
$111 nightly
The price is $124
Dec 6 - Dec 7
Total with taxes and fees
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
$108 nightly
The price is $121
Nov 17 - Nov 18
Total with taxes and fees
Vacation Village in the Berkshires
A cozy living room with a large window, wooden walls, and a television.

3. 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.
$190 nightly
The price is $213
Nov 12 - Nov 13
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

4. 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.
$190 nightly
The price is $213
Nov 12 - Nov 13
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

5. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
$190 nightly
The price is $213
Nov 12 - Nov 13
Total with taxes and fees
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

6. 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.
$104 nightly
The price is $116
Nov 18 - Nov 19
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

7. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
$237 nightly
The price is $265
Nov 17 - Nov 18
Total with taxes and fees
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

8. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
$190 nightly
The price is $213
Nov 12 - Nov 13
Total with taxes and fees
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

9. 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
$190 nightly
The price is $213
Nov 12 - Nov 13
Total with taxes and fees
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

10. 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.
$270 nightly
The price is $301
Nov 12 - Nov 13
Total with taxes and fees
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Room

11. 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
$190 nightly
The price is $213
Nov 12 - Nov 13
Total with taxes and fees
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

12. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (21 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
$248 nightly
The price is $279
Nov 15 - Nov 16
Total with taxes and fees
New Studio In Town, By the Water
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

13. 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.
$260 nightly
The price is $290
Nov 16 - Nov 17
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

14. 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.
$190 nightly
The price is $213
Nov 12 - Nov 13
Total with taxes and fees
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

15. 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.
$356 nightly
The price is $398
Nov 12 - Nov 13
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A hot tub with a string of lights above it, set against a dark night sky.

16. 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.
$335 nightly
The price is $374
Nov 12 - Nov 13
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Living area

17. 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
$270 nightly
The price is $304
Nov 15 - Nov 16
Total with taxes and fees
Downtown | Waterfront | Walk to Shops
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.

18. 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.
$320 nightly
The price is $357
Nov 15 - Nov 16
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
"Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping." ...Lina -- "the fire pit and creek are like a private oasis in the backyard." ... Nachama -- ( no firewood fees )

19. 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
$259 nightly
The price is $292
Nov 15 - Nov 16
Total with taxes and fees
2-Bdr Apt In Town, By the Water
A modern kitchen with a dining area, built-in shelves, and a large window.

20. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Lenox
$259 nightly
The price is $289
Nov 13 - Nov 14
Total with taxes and fees
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
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

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Top Berkshire County Hotel Reviews

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
Egremont

10/10 Excellent

So fantastic!! The cabins are gorgeous and very well appointed. We are going back!
United States
Emily
Reviewed July 7, 2025
Prospect Berkshires

Frequently Asked Questions

How many vacation rentals are available in Berkshire County?

Expedia has plenty of vacation rentals to choose from in and around Berkshire County, so you’re guaranteed to find the right one for you.


How much is a vacation rental in Berkshire County?

The selection of Berkshire County vacation rentals we have selected for you start as low as $115 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Berkshire County?

Vacation rentals in Berkshire County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Berkshire County vacation rentals to suit everyone.


Why should I choose a vacation rental in Berkshire County?

Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Berkshire County vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.


How do I find the best deal on a vacation rental in Berkshire County?

Find vacation rentals in Berkshire County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Berkshire County.


What amenities are available in a vacation rental in Berkshire County?

The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Berkshire County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Berkshire County?

Everytime is a great time to head to Berkshire County! Staying in a Berkshire County vacation rentals you will always find lots going on to keep you entertained.


Why book a vacation rental with Expedia?

Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Berkshire County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Berkshire County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Berkshire County, you can save even more.


Can I cancel my vacation rental through Expedia?

Yes, you can cancel or change your Berkshire County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.


Explore a world of travel with Expedia