A waterfall cascading over rocks in a forested area.

Holiday Homes in Hinsdale

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Hinsdale holiday homes

Coffee/tea maker, fridge, microwave, oven

1. 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)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is AU$306
includes taxes & fees
19 Aug - 20 Aug
NEW RENO - Chalet-style farm loft near Tanglewood
Outdoor dining

2. 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 clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is AU$776
includes taxes & fees
18 Aug - 19 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Smart TV

3. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (4 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is AU$555
includes taxes & fees
14 Sept - 15 Sept
stylish Berkshires Retreat
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is AU$430
includes taxes & fees
13 Sept - 14 Sept
Real Estate: Therapy - Lake, Laundry, Love it
Outdoor spa tub

5. 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$557
includes taxes & fees
25 Aug - 26 Aug
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

6. 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, (6 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$561
includes taxes & fees
9 Sept - 10 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
TV, DVD player, books, video library

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 AU$340
includes taxes & fees
14 Sept - 15 Sept
1800s Carriage house in Berkshires / Hudson Valley
A heated pool

8. 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 AU$784
includes taxes & fees
19 Aug - 20 Aug
Comfortable Berkshires retreat on mtn resort, SISO
Coffee/tea maker, fridge, microwave, stovetop

9. 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, (6 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is AU$786
includes taxes & fees
24 Aug - 25 Aug
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Interior

10. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AU$456
includes taxes & fees
19 Aug - 20 Aug
Cozy Riverside Berkshires Retreat
TV

11. 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 AU$815
includes taxes & fees
16 Sept - 17 Sept
Treetop Hideaway in Tyringham
Property grounds

12. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (41 reviews)
"Great hosts! Very nice and helpful. "
United States
Anonymous traveller
The price is AU$566
includes taxes & fees
31 Aug - 1 Sept
Charming, updated 3 bedroom farmhouse farm stay.
Exterior

13. 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 AU$842
includes taxes & fees
8 Sept - 9 Sept
1789 Shaker Farmhouse in Berkshires/Hudson Valley
4 bedrooms, travel cot, WiFi, bed sheets

14. 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.
The price is AU$1,189
includes taxes & fees
2 Sept - 3 Sept
Stylish Mid-century Modern Berkshires Cape
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 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$446
includes taxes & fees
1 Sept - 2 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
Outdoor dining

16. 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$1,579
includes taxes & fees
9 Sept - 10 Sept
Hancock Village Inn Near Jiminy Peak
Smart TV, fireplace, books

17. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (6 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 AU$974
includes taxes & fees
19 Aug - 20 Aug
5BR Berkshire Home Mins To The Mountain
Outdoor dining

18. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is AU$868
includes taxes & fees
30 Aug - 31 Aug
Stockbridge In-town Escape
Coffee/tea maker, fridge, microwave, oven

19. 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$570
includes taxes & fees
24 Aug - 25 Aug
Home in Great Barrington
Exterior

20. North Getaway Cottage

North Getaway Cottage
Williamstown
8.8 out of 10, Excellent, (27 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is AU$653
includes taxes & fees
31 Aug - 1 Sept
North Getaway Cottage
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Place was clean and well equipped, pool and amenities were great too !"
Nyra 3-night trip
Posted 4 hours ago
Vacation Village in the Berkshires

Find out more about Hinsdale

Hinsdale Holiday Homes information

Number of reviews
190
Accommodation
345 Holiday Homes
Lowest Price
AU$306
Highest Price
AU$1,579