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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 345 Vacation Homes in Hinsdale with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (242)
"Celebrate 34 anniversary great place. Better than a hotel. Love the place would stay again. Couldn’t figure out how to use Apple TV to watch Netflix. Just need a couple steak knives if you do take out or cook in. Had a great time. Thanks Ed"
The price is SAR 563
SAR 838 total
includes taxes & fees
3 May - 4 May
Berkshire Village Carriage House - Super Private!!
Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"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...
The price is SAR 2,059
SAR 3,882 total
includes taxes & fees
28 Apr - 29 Apr
Hancock Village Inn at Jiminy Peak
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Exterior

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

10.0 out of 10, Exceptional, (150)
"Very cozy, very clean, really enjoyed our stay. Marshall was a great host"
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Property grounds

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (71)
"Highly recommend this charming, historic place.  Well appointed. Has everything you need for your stay.  Cozy…yet plenty of space for everyone.  Looks like it was just renovated.  Took my daughter and two granddaughters for a ski weekend.  Wouldn’t hesitate to come back here.  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Spectacular views and close to Great Barrington.
Smart TV, fireplace

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (214)
"I love this place! It's been beautifully remodeled and is very comfortable. I would love to visit when it's warmer, but it's very cozy in the snow. I can't wait to come back with my kids. "
Peace and quiet on the lake
Lakeside Oasis Just You, The Lake & The View!
Exterior

Lakeside Oasis Just You, The Lake & The View!

9.8 out of 10, Exceptional, (70)
"It's a really lovely home on a beautiful property, with all the amenities we could have possibly needed, and also perfectly peaceful. The host was so welcoming and responsive, which made it that much nicer, too. My only regret is that we couldn't stay longer, and I would definitely want to stay there again. "
Lakeside Oasis Just You, The Lake & The View!
Heart of Lenox Walk to Town Cozy Cottage!
Fridge, microwave, oven, stovetop

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (70)
"Was as nice as the pictures. A plus for a very comfortable king sized bed! Right in town for walking to shops and restaurants. Thank you!"
Heart of Lenox Walk to Town Cozy Cottage!
Perfect Nature Haven In Great Barrington
Exterior

Perfect Nature Haven In Great Barrington

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."
Perfect Nature Haven In Great Barrington
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Property grounds

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (4)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Hilltown Nest is a wonderful place for family and friends to gather.
Property grounds

Hilltown Nest is a wonderful place for family and friends to gather.

9.8 out of 10, Exceptional, (15)
"Sadly we were only here for a couple of nights, but this place was very nice. I manage vacation rentals myself and i was very impressed by the cleanliness of this place, especially considering the size of it. The house is great for a family with lots of room to spread out. Our grandkids enjoyed tinkling on the piano and playing in the backyard. Would definitely choose to stay here again!"
Hilltown Nest is a wonderful place for family and friends to gather.
Mountain Blossom Retreat by Evergreen Home
A heated pool

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"Had a great long weekend getaway in Lanesboro. The property manager was super communicative, which was helpful. Would highly recommend!"
Mountain Blossom Retreat by Evergreen Home
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Terrace/patio

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (9)
"We had a great stay, thank you! Everything was great as all accommodations were met and other than getting food from the local nearby grocery store and our own personal things, nothing more was needed. Everything went so smoothly, other than our two dogs being home sick and whining at times, which ended up entailing a 7 hour round trip back home to leave them there with a sitter as we felt it was too much for our little fur babies to endure being in a strange place without us and better to...
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Quintessential 6-BR Berkshires Lodge
Exterior

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
Near Tanglewood: Historic Summer Retreat
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
Exterior

Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

10.0 out of 10, Exceptional, (10)
"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (121)
"Would definetely stay again.IF....LOL minor but not so minor.Need t.v. in master bedroom.Would not be a huge iinvestment.Cc"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Interior

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (46)
"What a wonderful property for our girls trip! The house is clean, there’s so much hangout space, and it’s so well supplied. "
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Interior

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.6 out of 10, Exceptional, (42)
"Ben and I enjoyed a good long weekend at the correctly described Beautiful Lenox Home. Mary, your host, has thought of everything to help you feel comfortable and very quickly to adjust to your home away from home. It is very well located so that you can easily visit the many places of interest nearby. The rules for checking in and out were clear and simple. We are delighted give this a 5-star rating. David and Ben will return, for sure!"
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.6 out of 10, Exceptional, (20)
"Our family (adults plus two teenage kids) loved our stay. The house sits behind and up the hill from the main house, and is private and quiet. The upstairs loft area with two separate beds was perfect for the kids, and we appreciated the well stocked kitchen. This was our family's favorite place on a recent college tour throughout New England."
The price is SAR 825
SAR 1,282 total
includes taxes & fees
27 Apr - 28 Apr
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.
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Other property types in Hinsdale

Berkshire Lake access
Lake

Berkshire Lake access

10.0 out of 10, Exceptional, (52)
"Joni is always great to work with, house is in a great location to Ashmere lake and is always well stocked with everything you need to enjoy your stay!"
Berkshire Lake access
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1799)
"What a beautiful place. Could not be more beautiful and we are so satisfied. We will be back!"
The price is SAR 348
SAR 422 total
includes taxes & fees
8 May - 9 May
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (928)
"Last minute find. Room was tidy/no odors. The kitchen was complete and cute wood art made the place feel cozy. The spare roll away bed was delivered as requested, and surprisingly comfortable. Traveled with hubby and 9 year old between seasons to hit Bash Bish. Will stay here again to visit Naumkeag."
The price is SAR 503
SAR 562 total
includes taxes & fees
26 Apr - 27 Apr
Jiminy Peak Mountain Resort
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.