A waterfall cascading over rocks in a forested area.

Hinsdale Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Hinsdale 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, (1,122 reviews)
"Clean & comfortable stay"
United States
Robert
The price is HK$624
HK$872 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

2. 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, (31 reviews)
"Excellent area for hiking the Berkshires! House is clean, comfortable, and perfect for cooking a quick dinner after showering off the mud and pine needles. Dog friendly. Right off the main street of a very nice neighborhood."
United States
Elizabeth G.
The price is HK$1,023
HK$2,536 total
includes taxes & fees
10 Sept - 11 Sept
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

3. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,603 reviews)
"All the amenities offered are an excellent plus. Good rates for rooms. Good place to stay at, lots to do even around the area"
United States
Alex
The price is HK$746
HK$919 total
includes taxes & fees
21 Sept - 22 Sept
Vacation Village in the Berkshires
A wooden cabin with a covered deck, a fire pit, and string lights.

4. Huttopia Berkshires

Huttopia Berkshires
2.5 star property
Williamstown
9.4 out of 10, Exceptional, (16 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$762
HK$851 total
includes taxes & fees
9 Sept - 10 Sept
Huttopia Berkshires
A modern kitchen with a dining area, a large window, and a view of the outdoors.

5. 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
The price is HK$1,764
HK$2,496 total
includes taxes & fees
9 Sept - 10 Sept
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
A wooden deck with a table and chairs, surrounded by a white railing.

6. 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 HK$2,463
HK$4,302 total
includes taxes & fees
5 Sept - 6 Sept
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

7. 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 HK$972
HK$2,032 total
includes taxes & fees
9 Sept - 10 Sept
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.

8. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (15 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 HK$1,137
HK$2,198 total
includes taxes & fees
13 Sept - 14 Sept
Penthouse Apartment on Park Street
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

9. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"Quiet location"
United States
Alicia S.
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
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.

10. 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$1,143
HK$2,941 total
includes taxes & fees
9 Sept - 10 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A hot tub with a string of lights above it, set against a dark night sky.

11. 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 HK$1,256
HK$3,084 total
includes taxes & fees
7 Sept - 8 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

12. 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$1,121
HK$2,225 total
includes taxes & fees
10 Sept - 11 Sept
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Cherry Plain State Park with a sandy beach, people relaxing, and a lake.

13. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (4 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is HK$1,095
HK$2,067 total
includes taxes & fees
14 Sept - 15 Sept
Berkshires Apartment at the Stephentown Hotel
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

14. 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 HK$596
HK$1,678 total
includes taxes & fees
10 Sept - 11 Sept
NEW RENO - Chalet-style farm loft near Tanglewood
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

15. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is HK$1,756
HK$4,345 total
includes taxes & fees
7 Sept - 8 Sept
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

16. 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$941
HK$1,997 total
includes taxes & fees
9 Sept - 10 Sept
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"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$416
HK$2,286 total
includes taxes & fees
13 Sept - 14 Sept
Real Estate: Therapy - Lake, Laundry, Love it
A wooden deck with two chairs and a table, overlooking a green landscape with a tree and hills.

18. Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
Riverbend Berkshire East Basecamp - 3 bedrooms available
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

19. 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 HK$1,019
HK$2,093 total
includes taxes & fees
9 Sept - 10 Sept
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

20. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.8 out of 10, Exceptional, (6 reviews)
"Good stay. Convenient to ski slopes. Thankful for Pet Friendly."
United States
Jim H.
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
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
"Clean room nice Kitchenette with everything."
Katherine 2-night trip
Posted 5 hours ago
Berkshire Mountain Lodge

Find out more about Hinsdale

Search for holiday rentals in Hinsdale on Expedia! You can easily find your home rentals, villas, holiday apartments in Hinsdale using one of the methods below:

  • View our selection of featured holiday rentals in Hinsdale
  • Use the map to find apartments and other holiday homes in the Hinsdale neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Hinsdale while they last

Look no further and take a look at our great range of rental properties in Hinsdale!

Frequently asked questions

Can I find a holiday rental in Hinsdale?

Yes, there are holiday rentals close to the most popular sights in Hinsdale, or you can select a more secluded option if you're looking for a relaxing stay. Hinsdale is known for its golf courses and restaurants. Make sure you have time to check out the shopping while you're in the area.

What are some of the best holiday rentals that Hinsdale has to offer?

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. : This highly rated holiday home rental in Hinsdale offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Hinsdale?

Expedia has 8 holiday rentals for your stay in Hinsdale.

What can I see and do in Hinsdale?

While exploring the area, visit family-friendly sights like Berkshire Museum, or get outside and enjoy nature at Ashmere Lake. Bas Ridge Golf Course and Wahconah Falls State Park are a couple of places you'll find in the wider area.

What are holiday rentals like in Hinsdale?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Hinsdale. Holiday rentals feature amenities like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a family trip.