A historic building with a tall tower, surrounded by lush green trees and a well-maintained lawn.

Vacation Rentals in Berkshire County

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Our top choices for Berkshire County vacation 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, (1,180 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
The price is ￥13,536
￥18,648 total
includes taxes & fees
Nov 1 - Nov 2
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, (2,712 reviews)
"Very pleased with our stay -great place for the family we will G-d willing return"
United States
Denton
The price is ￥13,619
￥16,945 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Village in the Berkshires
"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)

3. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (12 reviews)
"We had a great stay here. Clean, well-equipped, great location. Hope to come back again!"
United States
Tricia
The price is ￥19,456
￥44,119 total
includes taxes & fees
Nov 4 - Nov 5
Downtown | Waterfront | Walk to Shops
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 ￥22,936
￥45,231 total
includes taxes & fees
Oct 13 - Oct 14
Deluxe Mountain View Nautical Suite Jiminy 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)

5. 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 ￥18,982
￥42,684 total
includes taxes & fees
Nov 3 - Nov 4
New Studio In Town, By the Water
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
8.6 out of 10, Excellent, (7 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is ￥14,236
￥22,086 total
includes taxes & fees
Oct 14 - Oct 15
Cozy 1-bedroom studio in serene Great Barrington with AC
"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 )

7. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (21 reviews)
"Great place with easy access to town and even better access to a nice spot to hangout by the creek. I will definitely stay here again."
United States
Thomas
The price is ￥22,145
￥48,953 total
includes taxes & fees
Oct 19 - Oct 20
2-Bdr Apt In Town, By the Water
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

8. 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, (18 reviews)
"Nice Place"
United States
Tom C.
The price is ￥20,927
￥42,457 total
includes taxes & fees
Oct 8 - Oct 9
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Four people seated at a table with food and drinks, wearing winter sports helmets.

9. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (9 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
The price is ￥19,646
￥40,850 total
includes taxes & fees
Oct 8 - Oct 9
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.0 out of 10, Wonderful, (2 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 ￥13,762
￥52,477 total
includes taxes & fees
Nov 3 - Nov 4
Real Estate: Therapy - Lake, Laundry, Love it
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

11. 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 ￥17,938
￥38,764 total
includes taxes & fees
Oct 8 - Oct 9
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

12. 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, (34 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 ￥22,936
￥54,066 total
includes taxes & fees
Nov 2 - Nov 3
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
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.

13. 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 ￥25,198
￥61,894 total
includes taxes & fees
Oct 8 - Oct 9
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

14. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is ￥17,938
￥38,764 total
includes taxes & fees
Oct 8 - Oct 9
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

15. 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
The price is ￥21,354
￥43,112 total
includes taxes & fees
Oct 14 - Oct 15
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
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.

16. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.8 out of 10, Exceptional, (16 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 ￥22,936
￥44,524 total
includes taxes & fees
Oct 8 - Oct 9
Penthouse Apartment on Park Street
A hot tub with a string of lights above it, set against a dark night sky.

17. 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, (18 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥25,340
￥60,108 total
includes taxes & fees
Oct 12 - Oct 13
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

18. 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 ￥25,340
￥31,838 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Camper tucked into the woods
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

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

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.6 out of 10, Exceptional, (40 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 ￥32,174
￥74,633 total
includes taxes & fees
Oct 8 - Oct 9
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A sandy beach with a lake and forest in the background.

20. 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, (6 reviews)
"Amazing apartment! Clean, large, close walk to downtown Great Barrington. Joseph was an incredible host - accurate description, great communication. Will definitely be back!"
United States
Marc R.
The price is ￥33,060
￥51,771 total
includes taxes & fees
Oct 8 - Oct 9
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
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.
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Top Berkshire County Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Very spacious and inviting..Loved the coffee maker in lobby!!!! All the girls at the front desk were extremely nice and welcoming. Very clean property and great location.. to Great Barrington, Lenox, Stockbridge, and Lee with great restaurants near by in those towns as well"
Frank 2-night trip
Posted 21 hours ago
Berkshire Mountain Lodge

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Vacation Apartments in Berkshire County

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