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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Hinsdale vacation homes

A wooden deck with a table and chairs, surrounded by a white railing.

1. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (10 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is AED 1,098
AED 1,949 total
includes taxes & fees
2 Nov - 3 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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.

2. 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 AED 555
AED 1,400 total
includes taxes & fees
7 Oct - 8 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Pool

3. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is AED 591
AED 2,001 total
includes taxes & fees
4 Oct - 5 Oct
Comfortable Berkshires retreat on mtn resort, SISO
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

4. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is AED 305
AED 816 total
includes taxes & fees
7 Oct - 8 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A living room with a sofa, armchairs, a coffee table, and a television.

5. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (11 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is AED 1,297
AED 2,499 total
includes taxes & fees
19 Oct - 20 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

6. 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 AED 239
AED 1,128 total
includes taxes & fees
5 Oct - 6 Oct
Real Estate: Therapy - Lake, Laundry, Love it
A spacious living room with a dining area, a kitchen, and a large window.

7. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is AED 331
AED 850 total
includes taxes & fees
5 Oct - 6 Oct
1800s Carriage house in Berkshires / Hudson Valley
A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

8. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is AED 1,157
AED 2,538 total
includes taxes & fees
7 Oct - 8 Oct
Ellie’s Overlook, best view in the Berkshires!
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, (17 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AED 588
AED 1,441 total
includes taxes & fees
14 Oct - 15 Oct
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A modern living room with a sofa, armchair, coffee table, and TV.

10. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.4 out of 10, Exceptional, (3 reviews)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is AED 1,074
AED 2,156 total
includes taxes & fees
5 Oct - 6 Oct
Spacious Central Berkshires Home for Groups
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

11. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
Stylish Mid-century Modern Berkshires Cape
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

12. 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 AED 2,310
AED 4,216 total
includes taxes & fees
6 Oct - 7 Oct
Hancock Village Inn Near Jiminy Peak
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

13. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is AED 646
AED 2,059 total
includes taxes & fees
5 Oct - 6 Oct
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A white two-story house with a porch, surrounded by trees and a hill.

14. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is AED 771
AED 1,777 total
includes taxes & fees
5 Oct - 6 Oct
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

15. 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 AED 1,116
AED 2,273 total
includes taxes & fees
19 Oct - 20 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

16. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AED 779
AED 1,231 total
includes taxes & fees
26 Oct - 27 Oct
Home in Great Barrington
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

17. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is AED 1,039
AED 2,124 total
includes taxes & fees
28 Oct - 29 Oct
Treetop Hideaway in Tyringham
A bedroom with a bed, dresser, chair, and a flat-screen TV.

18. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (43 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
United States
Nancy M.
The price is AED 992
AED 1,631 total
includes taxes & fees
4 Oct - 5 Oct
Charming, updated 3 bedroom farmhouse farm stay.
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

19. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 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 AED 744
AED 1,163 total
includes taxes & fees
4 Oct - 5 Oct
Leaf-Peeper Paradise in the Berkshires
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

20. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is AED 1,197
AED 2,675 total
includes taxes & fees
4 Oct - 5 Oct
5BR Berkshire Home Mins To The Mountain
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 Hinsdale Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"I have stayed here multiple times. My unit this trip was very clean, well equipped and comfortable. The check in process and front desk staff were terrific. My only issue was a strong smell of marijuana coming through the slider and bedroom window . The staff gave me a fan to blow the smell back out however it was an issue throughout my stay."
Susan 7-night trip
Posted 5 hours ago
Berkshire Mountain Lodge

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