A rural landscape with snow-covered fields, a winding road, and scattered trees.

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

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, (32 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is £110
includes taxes & fees
8 Jul - 9 Jul
All the comforts of home
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (18 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is £252
includes taxes & fees
6 Jul - 7 Jul
Cozy Riverside Berkshires Retreat
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
10.0 out of 10, Exceptional, (1 review)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is £332
includes taxes & fees
13 Jul - 14 Jul
stylish Berkshires Retreat
Exterior

Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (11 reviews)
"We had an excellent experience. The place was wonderful. A real place to disconnect from everything. We Highly recommend it."
United States
Saul
The price is £266
includes taxes & fees
28 Jul - 29 Jul
Modern Luxurious Cabin, Catskills - The Tiny Nook
TV, offices

Catskill Stay w/ Deck & Fire Pit

Catskill Stay w/ Deck & Fire Pit
Catskill
9.0 out of 10, Wonderful, (4 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 £356
includes taxes & fees
6 Jul - 7 Jul
Catskill Stay w/ Deck & Fire Pit
Fridge, microwave, stovetop, dishwasher

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.6 out of 10, Exceptional, (4 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is £416
includes taxes & fees
1 Jul - 2 Jul
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Property grounds

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (9 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is £284
includes taxes & fees
1 Jul - 2 Jul
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Exterior

Cozy Catskill Escape

Cozy Catskill Escape
Catskill
The price is £207
includes taxes & fees
6 Jul - 7 Jul
Cozy Catskill Escape
TV

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is £388
includes taxes & fees
5 Jul - 6 Jul
Charles Cottage Near Warren St New Renovation
Exterior

Modern cabin retreat

Modern cabin retreat
Catskill
The price is £212
includes taxes & fees
6 Jul - 7 Jul
Modern cabin retreat
Exterior detail

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (3 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is £433
includes taxes & fees
7 Jul - 8 Jul
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Outdoor spa tub

Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is £218
includes taxes & fees
8 Jul - 9 Jul
Cabin Oasis near Town
Outdoor dining

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Hudson’
The price is £270
includes taxes & fees
1 Jul - 2 Jul
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Pool

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Our host was fantastic! She allowed us to check in early and check out late. The house was cozy and perfect for my girls weekend! "
United States
Kim W.
The price is £447
includes taxes & fees
1 Jul - 2 Jul
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Interior

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is £319
includes taxes & fees
1 Jul - 2 Jul
rural, serene + sophisticated space
Dining

Pool, Fireplace, Converted Barn! | Chic Barn House

Pool, Fireplace, Converted Barn! | Chic Barn House
Germantown
10.0 out of 10, Exceptional, (4 reviews)
"The property was exactly as described and has an excellent location, walking distance to the village shop but away from the main road. We especially appreciated the large, fenced, reasonably private yard and the lovely clean pool. "
United States
Anne L.
The price is £716
includes taxes & fees
1 Jul - 2 Jul
Pool, Fireplace, Converted Barn! | Chic Barn House
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (33 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is £327
includes taxes & fees
19 Jul - 20 Jul
Home in Great Barrington
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is £512
includes taxes & fees
6 Jul - 7 Jul
Treetop Hideaway in Tyringham
Pool

Charming Hudson Valley Escape | Heated Pool & Fire Pit

Charming Hudson Valley Escape | Heated Pool & Fire Pit
Claverack-Red Mills
10.0 out of 10, Exceptional, (1 review)
"amazing property - best rental i’ve ever stayed at. can’t recommend it enough"
United States
jessica c.
Charming Hudson Valley Escape | Heated Pool & Fire Pit
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is £597
includes taxes & fees
6 Jul - 7 Jul
Spacious 5-bedroom house in charming Lee with WiFi
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
"Well-maintained older property. Spacious suites. Accommodating staff. Great pool and location."
joann 4-night trip
Posted 3 hours ago
Berkshire Mountain Lodge

Find out more about Hillsdale

Hillsdale Holiday Homes information

Number of reviews
8,522
Accommodation
664 Holiday Homes
Lowest Price
£48
Highest Price
£215