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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Hillsdale holiday homes

Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (31 reviews)
"The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!"
United States
Olivia C.
The price is HK$832
HK$1,107 total
includes taxes & fees
26 Mar - 27 Mar
All the comforts of home
Dining

Super Comfortable Water-view Home in Saugerties

Super Comfortable Water-view Home in Saugerties
Saugerties
9.8 out of 10, Exceptional, (6 reviews)
"Very comfortable home, everything that’s needed is there "
United States
gianni g.
The price is HK$1,327
HK$4,804 total
includes taxes & fees
25 Mar - 26 Mar
Super Comfortable Water-view Home in Saugerties
Interior

Brand New House w gated backyard that is located right at the Saugerties Village

Brand New House w gated backyard that is located right at the Saugerties Village
Saugerties
10.0 out of 10, Exceptional, (41 reviews)
"Great new and clean property! Very close to downtown, supermarket, and a short drive to Hunter Mountain & Kaaterskill falls. "
United States
Michael
The price is HK$1,333
HK$3,159 total
includes taxes & fees
25 Mar - 26 Mar
Brand New House w gated backyard that is located right at the Saugerties Village
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is HK$1,445
HK$2,349 total
includes taxes & fees
30 Mar - 31 Mar
Home in Great Barrington
Exterior

Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (10 reviews)
"Great place. Exactly like the pictures. "
United States
robert a.
The price is HK$1,253
HK$2,665 total
includes taxes & fees
25 Mar - 26 Mar
Modern Luxurious Cabin, Catskills - The Tiny Nook
Exterior detail

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is HK$1,622
HK$2,669 total
includes taxes & fees
29 Mar - 30 Mar
3-bedroom house in beautiful Berkshires, close to amenities!
Interior

Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (19 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
The price is HK$963
HK$1,639 total
includes taxes & fees
10 Apr - 11 Apr
Catskill Cottage Walk to Downtown & River Views
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is HK$1,015
HK$2,856 total
includes taxes & fees
27 Mar - 28 Mar
Near Tanglewood: Historic Summer Retreat
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,586
HK$2,481 total
includes taxes & fees
25 Mar - 26 Mar
Cozy Riverside Berkshires Retreat
Interior

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is HK$1,184
HK$3,055 total
includes taxes & fees
30 Mar - 31 Mar
Historic Berkshires Home Near Tanglewood, Trails & Wineries
TV, offices

Catskill Stay w/ Deck & Fire Pit

Catskill Stay w/ Deck & Fire Pit
Catskill
8.8 out of 10, Excellent, (3 reviews)
"we had a great stay at this house with a group of friends - rooms were comfortable and kitchen had a lot of things we needed for meals. "
United States
raquel p.
The price is HK$1,071
HK$3,318 total
includes taxes & fees
30 Mar - 31 Mar
Catskill Stay w/ Deck & Fire Pit
Smart TV, fireplace

Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties

Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties
Saugerties
The price is HK$2,644
HK$5,137 total
includes taxes & fees
25 Mar - 26 Mar
Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties
TV, fireplace

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is HK$1,264
HK$4,003 total
includes taxes & fees
25 Mar - 26 Mar
Artists’ Hideaway in Old Chatham
Outdoor dining

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!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is HK$2,108
HK$3,754 total
includes taxes & fees
25 Mar - 26 Mar
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
TV, fireplace, printers

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, (4 reviews)
"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 HK$4,434
HK$10,404 total
includes taxes & fees
27 Mar - 28 Mar
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (35 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is HK$2,812
HK$5,687 total
includes taxes & fees
25 Mar - 26 Mar
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Fridge, microwave, oven, stovetop

Modern getaway in Catskills

Modern getaway in Catskills
Cairo
10.0 out of 10, Exceptional, (13 reviews)
"The host was accommodating and the house was very nice!"
United States
Ken B.
The price is HK$3,721
HK$6,591 total
includes taxes & fees
1 Apr - 2 Apr
Modern getaway in Catskills
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,856
HK$3,972 total
includes taxes & fees
29 Mar - 30 Mar
Cheerful 3-bedroom cottage with woodstove
Outdoor pool, a heated pool

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
Hudson
9.8 out of 10, Exceptional, (31 reviews)
"The home was as described. Exceptional. It was immaculate and well stocked."
United States
judy h.
The price is HK$4,778
HK$8,621 total
includes taxes & fees
14 Apr - 15 Apr
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is HK$2,068
HK$4,388 total
includes taxes & fees
30 Mar - 31 Mar
Treetop Hideaway in Tyringham
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 Hillsdale Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"very clean and friendly staff"
mohamed 2-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

Find out more about Hillsdale

Hillsdale Vacation Homes information

Number of reviews
332
Accommodation
641 Vacation Homes
Lowest Price
HK$1,107
Highest Price
HK$10,404

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