A waterfall cascading over rocks in a forested area.

Hinsdale Vacation 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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Hinsdale vacation rentals

Property grounds

1. 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, (39 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is ￥27,235
￥64,567 total
includes taxes & fees
Sep 13 - Sep 14
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Coffee/tea maker, fridge, microwave, oven

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)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
The price is ￥29,032
￥61,255 total
includes taxes & fees
Sep 19 - Sep 20
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Outdoor dining

3. 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 ￥45,929
￥78,583 total
includes taxes & fees
Oct 13 - Oct 14
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Smart TV, books

4. 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 ￥34,562
￥46,842 total
includes taxes & fees
Sep 14 - Sep 15
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Lobby

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,143 reviews)
"Clean & comfortable stay"
United States
Robert
The price is ￥12,227
￥17,090 total
includes taxes & fees
Oct 1 - Oct 2
Berkshire Mountain Lodge
A heated pool

6. 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 ￥24,731
￥83,332 total
includes taxes & fees
Sep 13 - Sep 14
Comfortable Berkshires retreat on mtn resort, SISO
Property grounds

7. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is ￥15,484
￥35,312 total
includes taxes & fees
Sep 14 - Sep 15
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Pool

8. 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 ￥14,793
￥34,369 total
includes taxes & fees
Sep 14 - Sep 15
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Indoor pool, a heated pool

9. 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 ￥14,793
￥34,197 total
includes taxes & fees
Sep 15 - Sep 16
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Gift shop

10. 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 ￥15,484
￥35,312 total
includes taxes & fees
Sep 14 - Sep 15
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Gift shop

11. 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.
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Gift shop

12. 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 ￥14,793
￥34,197 total
includes taxes & fees
Sep 15 - Sep 16
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Pool

13. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"Nice Place"
United States
Tom C.
The price is ￥14,793
￥34,197 total
includes taxes & fees
Sep 15 - Sep 16
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Pool

14. 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)
"Excellent communication with our host and property exactly as described. Easy check in/check out."
United States
Jillian G.
The price is ￥20,184
￥45,021 total
includes taxes & fees
Sep 15 - Sep 16
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Lobby

15. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,635 reviews)
"Great all around stay and lots for the kids to do"
United States
Sarah
The price is ￥14,614
￥18,009 total
includes taxes & fees
Sep 15 - Sep 16
Vacation Village in the Berkshires
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 ￥96,613
￥176,495 total
includes taxes & fees
Sep 15 - Sep 16
Hancock Village Inn Near Jiminy Peak
Interior

17. 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 ￥22,396
￥57,445 total
includes taxes & fees
Sep 14 - Sep 15
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Living area

18. 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 ￥22,273
￥43,238 total
includes taxes & fees
Sep 13 - Sep 14
Penthouse Apartment on Park Street
Outdoor spa tub

19. 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 ￥26,544
￥62,765 total
includes taxes & fees
Sep 15 - Sep 16
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

20. 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 ￥7,988
￥44,612 total
includes taxes & fees
Sep 16 - Sep 17
Real Estate: Therapy - Lake, Laundry, Love it
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

8/10 Good
"Beautiful views, friendly and responsive staff, property well kept. I would have given the highest praise except the indoor pool was closed for painting and maintenance. When I booked there was no notice in the website or Expedia. Since they had an outdoor pool and it was early fall, we swam theredes"
deb 2-night trip
Posted 1 hour 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 vacation rental in Hinsdale?

Yes, we offer vacation rentals close to the most popular attractions in Hinsdale, or you can go with a secluded option if you're looking for relaxation. 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's the top vacation rental in Hinsdale?

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. : Visitors give good reviews to this Hinsdale vacation home rental, which 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 vacation rentals are there in Hinsdale?

Expedia has 9 vacation 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 larger area.

What are vacation rentals like in Hinsdale?

Vacation rentals are privately owned properties you can reserve for a couple days or more in Hinsdale. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family getaway.