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The Berkshires Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for The Berkshires 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, (1,191 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
The price is HK$673
HK$927 total
includes taxes & fees
9 Nov - 10 Nov
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, (2,725 reviews)
"Very pleased with our stay -great place for the family we will G-d willing return"
United States
Denton
The price is HK$630
HK$790 total
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
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.

3. 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 HK$1,158
HK$2,959 total
includes taxes & fees
14 Oct - 15 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

4. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (54 reviews)
"Quiet and peaceful"
United States
Michael S.
The price is HK$1,923
HK$4,427 total
includes taxes & fees
23 Oct - 24 Oct
Cozy Cottage-Sunset On The Lake
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

5. 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 HK$589
HK$2,481 total
includes taxes & fees
3 Nov - 4 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

6. 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 HK$1,257
HK$1,580 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Camper tucked into the woods
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

7. 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, (8 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 HK$883
HK$1,293 total
includes taxes & fees
30 Oct - 31 Oct
Cozy 1-bedroom studio in serene Great Barrington with AC
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

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, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is HK$968
HK$2,028 total
includes taxes & fees
13 Oct - 14 Oct
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A hot tub with a string of lights above it, set against a dark night sky.

9. 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 HK$1,257
HK$2,982 total
includes taxes & fees
12 Oct - 13 Oct
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A snow-covered outdoor area with a fire pit, tables, and chairs.

10. 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 HK$939
HK$1,987 total
includes taxes & fees
14 Oct - 15 Oct
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

11. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is HK$1,745
HK$2,729 total
includes taxes & fees
13 Oct - 14 Oct
Home in Great Barrington
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, (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 HK$1,640
HK$2,577 total
includes taxes & fees
12 Oct - 13 Oct
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
"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)

13. 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 HK$965
HK$2,189 total
includes taxes & fees
4 Nov - 5 Nov
Downtown | Waterfront | Walk to Shops
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

14. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.6 out of 10, Exceptional, (7 reviews)
"Excellent communication with our host and property exactly as described. Easy check in/check out."
United States
Jillian G.
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
A staircase with a wooden handrail and a white wall with a light switch.

15. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (28 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 HK$1,530
HK$2,411 total
includes taxes & fees
26 Oct - 27 Oct
Leaf-Peeper Paradise in the Berkshires
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

16. 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 HK$1,138
HK$2,682 total
includes taxes & fees
5 Nov - 6 Nov
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A spacious living area with a high ceiling, a kitchen in the background, and a large abstract painting on the wall.

17. Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Hancock
9.6 out of 10, Exceptional, (4 reviews)
"Excellent instructions by the owner for the check in process, which was easy. The room was beautiful and very clean, and exactly as advertised. We would absolutely recommend and stay again!!"
United States
Chad J.
The price is HK$1,287
HK$2,516 total
includes taxes & fees
11 Nov - 12 Nov
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

18. 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 HK$1,624
HK$3,734 total
includes taxes & fees
13 Oct - 14 Oct
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

19. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. "
United States
Eileen O.
The price is HK$968
HK$2,028 total
includes taxes & fees
13 Oct - 14 Oct
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

20. Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Hancock
9.8 out of 10, Exceptional, (21 reviews)
"Great location! "
United States
shannon m.
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
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 The Berkshires Hotel Reviews

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Nice establishment with great staff. Good heated outdoor pool. Great location. Great activities all seasons. Apartments are well-worn and are not pristine. Not for clean-freaks. Nicer than a college apartment."
Guinevere 1-night trip
Posted 10 hours ago
Jiminy Peak Mountain Resort

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