A waterfall cascading over rocks in a forested area.

Hinsdale Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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$1,898
HK$4,073 total
includes taxes & fees
27 Jul - 28 Jul
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Property grounds

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
10.0 out of 10, Exceptional, (2 reviews)
"The room was clean and well appointed with ample bedding, towels, electrical outlets and fans (it was a very hot weekend). The house is spacious and the bathroom was well equipped. The host was very responsive to a question about off hours arrival. HIghly recommend."
United States
Mary M.
The price is HK$855
HK$1,069 total
includes taxes & fees
22 Jul - 23 Jul
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Interior

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
The price is HK$847
HK$1,725 total
includes taxes & fees
2 Aug - 3 Aug
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Dining

Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse
Lanesborough
9.4 out of 10, Exceptional, (40 reviews)
"Clean, friendly, but isolated. On premises coffee shop was a bonus."
United States
Karl K.
Charming Apt in 18th c Berkshire Farmhouse
Outdoor dining

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (8 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is HK$980
HK$2,222 total
includes taxes & fees
21 Jul - 22 Jul
Downtown | Waterfront | Walk to Shops
Room

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.2 out of 10, Wonderful, (12 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$1,235
HK$1,379 total
includes taxes & fees
22 Jul - 23 Jul
Huttopia Berkshires
Property grounds

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
9.0 out of 10, Wonderful, (17 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
The price is HK$903
HK$1,946 total
includes taxes & fees
21 Jul - 22 Jul
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Outdoor dining

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (14 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
The price is HK$980
HK$2,267 total
includes taxes & fees
21 Jul - 22 Jul
2-Bdr Apt In Town, By the Water
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$924
HK$1,970 total
includes taxes & fees
21 Jul - 22 Jul
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Outdoor dining

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (8 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
The price is HK$903
HK$1,946 total
includes taxes & fees
21 Jul - 22 Jul
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Outdoor dining

Dadzpad Cabin in Stephentown

Dadzpad Cabin in Stephentown
Stephentown
5.0 out of 10, (2 reviews)
"House was clean and comfortably furnished. The kids enjoyed the arcade games and it was an overall good time. Only Issues were that the drive and walk ways were hidden in the snow and the house did not hold heat well "
United States
Quinn R.
The price is HK$882
HK$1,710 total
includes taxes & fees
27 Jul - 28 Jul
Dadzpad Cabin in Stephentown
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,460 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
The price is HK$1,032
HK$1,239 total
includes taxes & fees
17 Aug - 18 Aug
Vacation Village in the Berkshires
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$1,581
HK$3,298 total
includes taxes & fees
21 Jul - 22 Jul
stylish Berkshires Retreat
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$1,517
HK$3,411 total
includes taxes & fees
28 Jul - 29 Jul
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Coffee/tea maker, fridge, microwave, stovetop

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.6 out of 10, Exceptional, (5 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is HK$1,380
HK$4,456 total
includes taxes & fees
21 Jul - 22 Jul
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is HK$1,137
HK$3,179 total
includes taxes & fees
22 Jul - 23 Jul
Real Estate: Therapy - Lake, Laundry, Love it
Outdoor dining

New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (15 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is HK$941
HK$2,116 total
includes taxes & fees
21 Jul - 22 Jul
New Studio In Town, By the Water
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$1,756
HK$4,345 total
includes taxes & fees
21 Jul - 22 Jul
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Beach

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is HK$1,207
HK$2,280 total
includes taxes & fees
26 Jul - 27 Jul
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Coffee/tea maker, fridge, microwave, oven

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (34 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is HK$2,352
HK$3,485 total
includes taxes & fees
9 Aug - 10 Aug
Home in Great Barrington
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Hinsdale Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"The room was neat and had access to outside to enjoy sitting. The fridge in the room was a convenient size for cold and frozen foods. The staff was responsive to issues, even when I told them they could wait to fix it until after we left (it was fixed quickly. The breakfast was excellent and offered a nice variety. Would happily stay here again."
MaryLou 3-night trip
Posted 2 hours ago
The Yankee Inn

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 Colonial Theater 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.