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Hinsdale Vacation Rentals

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Check prices for these dates

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Nov 30 - Dec 1
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Dec 1 - Dec 2
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Dec 5 - Dec 7
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Dec 12 - Dec 14

Vacation Rentals in Hinsdale

Property grounds
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Vacation Home in Hinsdale

9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cabin in Hinsdale

9.8 out of 10, Exceptional, (34)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Lobby
Vacation Village in the Berkshires

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2157)
"Great place!"
United States
Nicole
The price is ￥12,734
￥15,937 total
includes taxes & fees
Dec 2 - Dec 3
Vacation Village in the Berkshires
Exterior
Huttopia Berkshires

Camping in Williamstown

1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is ￥26,566
￥29,675 total
includes taxes & fees
Dec 16 - Dec 17
Huttopia Berkshires
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

3.0 star property
8.2 out of 10, Very Good, (986)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is ￥28,929
￥32,314 total
includes taxes & fees
Dec 2 - Dec 3
Jiminy Peak Mountain Resort
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (134)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The Ponds at Foxhollow
Game room
Pet Friendly Riverfront Home in Great Barrington

Vacation Home in Great Barrington

9.4 out of 10, Exceptional, (6)
The price is ￥31,626
￥46,491 total
includes taxes & fees
Dec 2 - Dec 3
Pet Friendly Riverfront Home in Great Barrington
Interior
Peace and quiet on the lake

Vacation Home in Sherwood Forest

9.6 out of 10, Exceptional, (230)
"Great communication, comfortable home, love the location"
United States
Susan C.
Peace and quiet on the lake
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Vacation Home in Lee

8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is ￥66,377
￥124,560 total
includes taxes & fees
Dec 7 - Dec 8
Spacious 5-bedroom house in charming Lee with WiFi
Exterior
Bear Creek Cabin

Cabin in Charlemont

10.0 out of 10, Exceptional, (43)
"We enjoyed our stay!!"
United States
Hillary S.
The price is ￥62,472
￥93,508 total
includes taxes & fees
Dec 2 - Dec 3
Bear Creek Cabin
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

Villa in Lenox

10.0 out of 10, Exceptional, (17)
"Perfect house for our family reunion. Everything was perfect."
United States
Michael C.
The Kemble- Built by a US Secretary of State in Lenox
Exterior
Club Wyndham Bentley Brook Resort - 2 Bedroom

Condo in Hancock

8.0 out of 10, Very Good, (4)
"Great spot for family ski trip. Location was great. Condo and amenities were great. Overall super happy and would stay again. "
United States
Ellamae G.
Club Wyndham Bentley Brook Resort - 2 Bedroom
Smart TV, fireplace, DVD player
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Vacation Home in Great Barrington

10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥22,771
￥58,756 total
includes taxes & fees
Dec 2 - Dec 3
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Outdoor pool
The Clearing - Quiet - Close To Nature

Cottage in Cummington

10.0 out of 10, Exceptional, (210)
"This was the perfect little home for my husband and I to stay for a few days while we visited the area. Loved it."
Canada
Andrea F.
The Clearing - Quiet - Close To Nature
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Vacation Home in Hancock

9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is ￥50,290
￥114,407 total
includes taxes & fees
Dec 2 - Dec 3
Comfortable Berkshires retreat on mtn resort, SISO
Property grounds
Experience Three Sisters Sanctuary in Goshen, MA

Vacation Home in Goshen

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had such a great time staying here as always. "
United States
David F.
Experience Three Sisters Sanctuary in Goshen, MA
Exterior
Hancock Village Inn Near Jiminy Peak

Vacation Home in Hancock

10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is ￥85,743
￥163,582 total
includes taxes & fees
Dec 2 - Dec 3
Hancock Village Inn Near Jiminy Peak
Outdoor dining
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Vacation Home in Pittsfield

9.8 out of 10, Exceptional, (150)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
United States
Sarah A.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.

Vacation Home in Lenox

9.2 out of 10, Wonderful, (33)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.
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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Great stay, great breakfast"
Peter 1-night trip
Posted 10 hours ago
Hampton Inn & Suites Berkshires-Lenox

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 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 8 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 Kennedy Park. Bas Ridge Golf Course and Crane Museum of Papermaking 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.