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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Vacation Homes in Hinsdale

Private kitchen
Home in the Woods

Home in the Woods

Russell
10.0 out of 10, Exceptional, (3)
"Jessica's spot is adorable and tidy, at the end of a quiet, shady lane, with lots of peace and privacy. It was a hot, muggy weekend but there were 2 window units and extra fans to keep us comfortable. The house is well-appointed—we had a busy schedule and were sad we didn't have a chance to use the lovely outdoor fire pit area. Good communication after a minor mixup. Would definitely stay again!"
United States
Jennifer F.
The price is AED 621
AED 1,176 total
includes taxes & fees
16 Nov - 17 Nov
Home in the Woods
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"Nicole was phenomenal, the most speedy and responsive host I've had on any platform. The A-Frame was a perfect, cozy, and quaint little spot for our weekend getaway. It was clean and honestly portrayed in the photos. No complaints whatsoever. Thank you, Nicole!"
United States
James F.
The price is AED 536
AED 1,386 total
includes taxes & fees
16 Nov - 17 Nov
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
TV
Florida Mountain Log Cabin

Florida Mountain Log Cabin

2.0 star property
Florida
10.0 out of 10, Exceptional, (4)
"We loved our 1 night stay here - it is a super cute log cabin with comfortable beds and very clean! Our favorite part was the fire pit for smores and the kids especially loved the cozy swings! Host was very accessible. Definitely recommend!"
United States
Kate R.
The price is AED 675
AED 1,245 total
includes taxes & fees
25 Nov - 26 Nov
Florida Mountain Log Cabin
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is AED 588
AED 1,441 total
includes taxes & fees
16 Nov - 17 Nov
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (25)
"We had a lovely one week stay at this property. The location was very convenient to all the restaurants and shops. The fall foliage was spectacular and truly enjoyed biking and hiking in the Berkshires."
United States
Farida K.
The price is AED 579
AED 970 total
includes taxes & fees
16 Nov - 17 Nov
Home in Great Barrington
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs
9.0 out of 10, Wonderful, (19)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is AED 502
AED 1,373 total
includes taxes & fees
16 Nov - 17 Nov
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is AED 496
AED 890 total
includes taxes & fees
17 Nov - 18 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior
North Getaway Cottage

North Getaway Cottage

Williamstown
9.4 out of 10, Exceptional, (23)
"The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. "
United States
Mary Alice H.
The price is AED 744
AED 1,635 total
includes taxes & fees
17 Nov - 18 Nov
North Getaway Cottage
Fridge, microwave, oven, stovetop
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!

2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is AED 988
AED 1,806 total
includes taxes & fees
16 Nov - 17 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior
Bungalow in the Berkshires

Bungalow in the Berkshires

Lee
10.0 out of 10, Exceptional, (4)
"Great location, very clean and well appointed with everyth"
United States
Nick R.
The price is AED 1,010
AED 1,415 total
includes taxes & fees
30 Nov - 1 Dec
Bungalow in the Berkshires
Game room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.0 out of 10, Wonderful, (4)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AED 744
AED 1,085 total
includes taxes & fees
23 Nov - 24 Nov
Pet Friendly Riverfront Home in Great Barrington
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Great Barrington Get Away

Great Barrington
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is AED 1,047
AED 1,912 total
includes taxes & fees
16 Nov - 17 Nov
Great Barrington Get Away
Property grounds
Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont
The price is AED 588
AED 1,518 total
includes taxes & fees
18 Nov - 19 Nov
Riverbend Berkshire East Basecamp - 3 bedrooms available
Fridge, microwave, oven, stovetop
The Greylock Cabin

The Greylock Cabin

Florida
10.0 out of 10, Exceptional, (4)
"We really enjoyed our stay at Greylock Cabin! It is clean, well maintained, and was very prepared for our arrival. Extra towels, bedding, and basic cookware were helpful for a comfortable getaway. It was easy to access the cabin and park. The host was very communicative and easy to reach throughout our stay. The outdoor space had a great view and was perfect to grill and unwind by the fire."
United States
Robert G.
The price is AED 955
AED 1,596 total
includes taxes & fees
14 Dec - 15 Dec
The Greylock Cabin
Exterior
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock
9.8 out of 10, Exceptional, (72)
"Awesome place to stay to ski for the weekend. Skiing on and off was very easy, quick ride to dinner and plenty of room in the condo for everyone. Can’t wait to come back!"
United States
Christine L.
The price is AED 970
AED 2,019 total
includes taxes & fees
16 Nov - 17 Nov
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
9.0 out of 10, Wonderful, (7)
"Family ski trip was made extremely enjoyable by staying at this property. Everything worked out as advertised"
United States
Henry C.
The price is AED 1,183
AED 2,662 total
includes taxes & fees
16 Nov - 17 Nov
Comfortable Berkshires retreat on mtn resort, SISO
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is AED 1,561
AED 2,905 total
includes taxes & fees
1 Dec - 2 Dec
Spacious 5-bedroom house in charming Lee with WiFi
Exterior
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (15)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
United States
Jim O.
The price is AED 2,200
AED 4,081 total
includes taxes & fees
9 Dec - 10 Dec
Hancock Village Inn Near Jiminy Peak
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington
10.0 out of 10, Exceptional, (1)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is AED 2,089
AED 4,890 total
includes taxes & fees
16 Nov - 17 Nov
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington
The price is AED 1,249
AED 2,105 total
includes taxes & fees
19 Nov - 20 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"The room was nice, but wish we would have asked for the lake view. The breakfast area was really nice and they had good food. The coffee machine was available 24/7 and it made a pretty good mocha! "
terri 1-night trip
Posted 3 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel