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Compare 264 Vacation Homes in Hinsdale with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is SAR 548
SAR 839 total
includes taxes & fees
2 Dec - 3 Dec
Berkshire Village Carriage House - Super Private!!

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

10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is SAR 984
SAR 2,013 total
includes taxes & fees
2 Dec - 3 Dec
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

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

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake

Cozy apartment located in quiet Williamsburg

9.4 out of 10, Exceptional, (47)
"Convenient location, comfortable."
The price is SAR 563
SAR 972 total
includes taxes & fees
2 Dec - 3 Dec
Cozy apartment located in quiet Williamsburg

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

10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

10.0 out of 10, Exceptional, (20)
"clean, wonderful views of the lake. "
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

Berkshire Ski House on Lake Garfield w/HT By Great Barrington

10.0 out of 10, Exceptional, (3)
"We had a lovely stay! The space was perfect for our group of 4 moms looking for a peaceful getaway. The host was very responsive. Only note for those visiting, rideshares (Uber and otherwise) are few and far between. Schedule ahead! We'd definitely stay again :)"
Berkshire Ski House on Lake Garfield w/HT By Great Barrington

Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

10.0 out of 10, Exceptional, (33)
"We had a wonderful time at this property! It was perfect for what we wanted- a place to ourselves in nature with beautiful views. Host was great! Would definitely recommend! "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

Quintessential 6-BR Berkshires Lodge

9.8 out of 10, Exceptional, (8)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

10.0 out of 10, Exceptional, (90)
"Very clean, spacious, and comfortable. Property manager’s information was helpful."
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (82)
"My mom and I did a mother/daughter trip to the Berkshires in October. Everything about this property is perfect! Location was 5/10 min from groceries/restaurants but felt like we were in the middle of nowhere. The house itself was very clean and so comfortable (the bed felt like a dream)! We spent our days exploring the surrounding towns and our evenings relaxing at he house. We saw deer in the mornings and 2 bald eagles! Thank you for the incredible stay!! "
Hearts Desire is a furnished whole house in a small, colorful garden center.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (10)
"As advertised "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Plainfield House in a 10,000 acre state forest and private pond

9.6 out of 10, Exceptional, (82)
"Perry was awesome and easy to connect with. Beds were all very comfortable and there are 2 large bathrooms easy to share with a big family. Everything is labeled in the house and it makes it so easy to do everything. We will look forward to staying here in the future! "
Plainfield House in a 10,000 acre state forest and private pond

Woodland Zen by AvantStay | Modern Design + Patio

10.0 out of 10, Exceptional, (5)
"This home is large, full of light and has modern decor. Mostly bare floors so bring slippers/socks for cold nights. Fully appointed kitchen that has everything, including plenty of trash bags, dish soap, pots, pans, dishes, etc. We cooked several meals there and it was easy to do. Bedroom windows have blinds, bathroom windows do not! The house is surrounded by trees but showering in a room with bare windows took some getting used to. There are many light switches that some labeling might be...
Woodland Zen by AvantStay | Modern Design + Patio

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (15)
"Amanda is a very responsive and accommodating host. The house was comfortable and perfect for our girls weekend with plenty of space for us to relax and feel at home. "
The price is SAR 507
SAR 1,280 total
includes taxes & fees
9 Dec - 10 Dec
Near Tanglewood: Historic Summer Retreat

Great Barrington Walkable to Lake and Town!

9.6 out of 10, Exceptional, (5)
"Needed a rental in a hurry, lucked into Lucas’ house. Quiet, comfortable and cozy. Great visit. Thank you for hosting me and Birdie. "
Great Barrington Walkable to Lake and Town!

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (65)
"Beautiful home perfect for our multi-generational family. We loved the separate spaces and easy walk to the town center. We can’t wait to come back!"
Enjoy comfortable elegance in this secluded grand home located in town

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life
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

10.0 out of 10, Exceptional, (47)
"The house was very clean and the yard is large. It's a great place for family vacations."
Berkshire Lake access

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

10.0 out of 10, Exceptional, (23)
"My partner and I really enjoyed our relaxing stay at this quaint cottage. It was clean, comfortable, and tucked away in a very quiet area. It was easy to get to restaurants and theaters in Pittsfield / Lenox / Stockbridge. The hot tub was also a great way to spend a cozy fall afternoon!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1746)
"Property was beautiful, great staff "
The price is SAR 634
SAR 733 total
includes taxes & fees
2 Dec - 3 Dec
Vacation Village in the Berkshires
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.