A waterfall cascading over rocks in a forested area.

Hinsdale Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Hinsdale holiday rentals

Property grounds

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

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (38 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
The price is HK$1,475
HK$3,540 total
includes taxes & fees
27 Jul - 28 Jul
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.

Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.
Hinsdale
10.0 out of 10, Exceptional, (8 reviews)
"Kendra was an excellent host! Very nice and welcoming and answered questions promptly. The house was beautiful and the country setting and lake was picturesque. "
United States
Joseph L.
Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,024 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is HK$871
HK$1,148 total
includes taxes & fees
25 Aug - 26 Aug
Berkshire Mountain Lodge
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,475 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
The price is HK$856
HK$1,042 total
includes taxes & fees
18 Aug - 19 Aug
Vacation Village in the Berkshires
Coffee/tea maker, fridge, microwave, oven

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, (28 reviews)
"Clean and just as pictured. Comfortable bed and furniture"
United States
Kathleen O.
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Outdoor dining

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, (9 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is HK$2,463
HK$4,320 total
includes taxes & fees
28 Jul - 29 Jul
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Beach nearby

Beachwood Cottage

Beachwood Cottage
Stockbridge
9.8 out of 10, Exceptional, (6 reviews)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
United States
Christine P.
The price is HK$2,470
HK$4,660 total
includes taxes & fees
6 Aug - 7 Aug
Beachwood Cottage
Outdoor dining

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 HK$5,344
HK$9,541 total
includes taxes & fees
27 Jul - 28 Jul
Hancock Village Inn Near Jiminy Peak
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 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 HK$1,694
HK$3,452 total
includes taxes & fees
3 Aug - 4 Aug
stylish Berkshires Retreat
Pool

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.
The price is HK$840
HK$1,867 total
includes taxes & fees
27 Jul - 28 Jul
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Room

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (13 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$946
HK$1,056 total
includes taxes & fees
23 Aug - 24 Aug
Huttopia Berkshires
Gift shop

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, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is HK$840
HK$1,867 total
includes taxes & fees
27 Jul - 28 Jul
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Outdoor dining

NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (5 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is HK$2,180
HK$4,371 total
includes taxes & fees
27 Jul - 28 Jul
NEW RENO Historic Creamery in Berkshires w/hot tub
Outdoor spa tub

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$1,376
HK$3,228 total
includes taxes & fees
28 Jul - 29 Jul
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Exterior

1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (4 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 HK$2,086
HK$4,322 total
includes taxes & fees
27 Jul - 28 Jul
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Interior

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, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,670
HK$3,600 total
includes taxes & fees
25 Aug - 26 Aug
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Interior

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$1,757
HK$4,346 total
includes taxes & fees
27 Jul - 28 Jul
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Living area

Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (14 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$2,208 total
includes taxes & fees
24 Aug - 25 Aug
Penthouse Apartment on Park Street
Dining

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.
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Gift shop

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is HK$840
HK$1,867 total
includes taxes & fees
27 Jul - 28 Jul
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
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

Berkshires Untold

Berkshires Untold

8/10 Good
"Nice room, nice bar, fire pit. Don’t eat dinner there."
Kathleen 2-night trip
Posted 11 hours ago
Berkshires Untold

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:

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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.