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Compare 717 Vacation Homes in Hillsdale with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (240)
"Great experience....very clean facility in excellent condition......except for driveway & sidewalk. Sheet of ice....yes there were unusual conditions this winter, but I would be concerned for any elderly or uncoordinated guests."
The price is SAR 563
SAR 851 total
includes taxes & fees
2 Apr - 3 Apr
Berkshire Village Carriage House - Super Private!!

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (16)
"Host was eary to communicate with. My kids enjoyed the games. Great view looking over the Hudson River. Easily accessible to town, Kingston, or Ski areas. Definitely would return!"
Hamptons on the Hudson in South Saugerties

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 2,060
SAR 3,882 total
includes taxes & fees
29 Mar - 30 Mar
Hancock Village Inn at Jiminy Peak

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.

Lakeside Retreat Just You, The Lake & The View!

9.8 out of 10, Exceptional, (69)
"We had a lovely stay. Views are amazing. Property owner was very responsive and helpful. Would love to go back in the fall."
Lakeside Retreat Just You, The Lake & The View!

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (25)
"Our family of 4 stayed here while skiing at Catamount - great proximity, exactly as pictured, clean, and perfect size. Host was responsive - would stay here again!"
The price is SAR 596
SAR 1,248 total
includes taxes & fees
27 Apr - 28 Apr
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

9.0 out of 10, Wonderful, (22)
"This was the perfect cozy home for a few nights away. Gorgeous property and welcoming vibes. "
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

Secluded Lux Mansion Pool Home with Amazing Views

10.0 out of 10, Exceptional, (1)
"We had a great time staying in the house for the weekend as a group of 10. Kitchen and bathrooms are well-stocked. The living room couch is enormous. All of the bedrooms are bright and cozy. The views and property are absolutely stunning. Had we been fewer, we probably would have used the outdoor firepits. Barry and Alisha are lovely and helpful hosts -- they sent along a great list of food reccs ahead of time, responded quickly when I couldn't find a few things, etc. "
Secluded Lux Mansion Pool Home with Amazing Views

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (69)
"Cottage is a very short walk to town. Clean and well appointed space. Tom was extremely responsive to any messages. Would stay again."
Heart of Lenox Walk to Town Cozy Cottage!

Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

10.0 out of 10, Exceptional, (46)
"We had the most wonderful time! The views are unbelievable - sitting in the pool or hot tub or around the fire pit, watching the barges sail by was so special! We can’t wait to come back!"
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (24)
"Beautiful, remote property perfect for large groups! We'll definitely try get back there in the summer!"
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (35)
"The property was centrally located for skiing, and was a comfortable stay."
The price is SAR 739
SAR 1,672 total
includes taxes & fees
24 Apr - 25 Apr
Cheerful 3-bedroom cottage with woodstove

Perfect Nature Retreat 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 Retreat In Great Barrington

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

10.0 out of 10, Exceptional, (3)
"Our group of 8 were happy in this comfy home. The kitchen was well appointed with everything we needed. The bedding, towels and toiletries provided were very much appreciated. The cozy living room with the pellet stove has a beautiful view for morning coffee. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

The Best 3-bedroom house in Tivoli

The Best 3-bedroom house in Tivoli

Cozy Hudson River Waterfront, 3 Bdrm Pool/Quiet Street/Great Views/HITS 2 miles

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great pool on the river! Loved watching th La ge barges go by! "
Cozy Hudson River Waterfront, 3 Bdrm Pool/Quiet Street/Great Views/HITS 2 miles

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

9.4 out of 10, Exceptional, (8)
"The location was great and just a short walk to downtown. We thought the pictures on the site were a bit misleading. The house looked a little more open than it actually was, especially in the kitchen. The outside fire pit area was a little run down. A chair was broken and the string lights were down on the ground, water filled and no outlet to plug into. Plenty of bed space for everyone to sleep and beds were comfortable. Plenty of extra sheets and towels and the kitchen was well equipped. We...
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Private Estate, Heated Yearround Outdoor Pool

9.8 out of 10, Exceptional, (17)
"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "
Private Estate, Heated Yearround Outdoor Pool

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
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 Hillsdale

Postcard Cabins Eastern Catskills

2.0 star property
8.4 out of 10, Very Good, (5)
"We love our Bartow cabin, it was so cozy and relaxing for us. A perfect getaway from the city life. Will definitely stay again. "
The price is SAR 657
SAR 709 total
includes taxes & fees
2 Apr - 3 Apr
Postcard Cabins Eastern Catskills

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (94)
"Lovely caring owner. Beautiful room Hope to stay there again!"
The price is SAR 487
SAR 526 total
includes taxes & fees
10 Apr - 11 Apr
Micosta Leisure Inn

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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.