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

Holiday Homes in Hillsdale

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Check prices for these dates

In two weeks
3 July - 5 July
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Hillsdale holiday homes

Interior

Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (22 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
The price is AU$241
includes taxes & fees
28 June - 29 June
Catskill Cottage Walk to Downtown & River Views
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 AU$204
includes taxes & fees
30 June - 1 July
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, (7 reviews)
"Very comfortable home, everything that’s needed is there "
United States
gianni g.
The price is AU$926
includes taxes & fees
23 June - 24 June
Super Comfortable Water-view Home in Saugerties
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (16 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AU$457
includes taxes & fees
24 June - 25 June
Cozy Riverside Berkshires Retreat
TV, fireplace, books

NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
The price is AU$918
includes taxes & fees
23 June - 24 June
NEW: Chic Modern Barn Style Home in Fun Area
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 AU$575
includes taxes & fees
24 June - 25 June
Catskill Stay w/ Deck & Fire Pit
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is AU$537
includes taxes & fees
23 June - 24 June
Near Tanglewood: Historic Summer 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 AU$485
includes taxes & fees
8 July - 9 July
Modern Luxurious Cabin, Catskills - The Tiny Nook
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 AU$790
includes taxes & fees
30 June - 1 July
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, (6 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is AU$535
includes taxes & fees
23 June - 24 June
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
TV

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is AU$720
includes taxes & fees
23 June - 24 June
Charles Cottage Near Warren St New Renovation
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 reviews)
"Perfect space for an overnight stay. Very clean and well appointed. Communication from host was great and check in was a breeze. 2 minute drive from downtown Great Barrington."
United States
Anonymous traveller
The price is AU$524
includes taxes & fees
23 June - 24 June
Home in Great Barrington
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 AU$672
includes taxes & fees
29 June - 30 June
stylish Berkshires 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 AU$710
includes taxes & fees
23 June - 24 June
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy Family Friendly home near Hunter Mt, Katerskill Falls & hiking trails

Cozy Family Friendly home near Hunter Mt, Katerskill Falls & hiking trails
Catskill
10.0 out of 10, Exceptional, (1 review)
"Great and funny time thanks owner you very kindly "
United States
Gabdulkarim Z.
The price is AU$761
includes taxes & fees
23 June - 24 June
Cozy Family Friendly home near Hunter Mt, Katerskill Falls & hiking trails
Fridge, microwave, oven, stovetop

NEW: Chic Family Home in Boutique Town

NEW: Chic Family Home in Boutique Town
Catskill
10.0 out of 10, Exceptional, (1 review)
"As described."
United States
kimberly j.
The price is AU$1,003
includes taxes & fees
23 June - 24 June
NEW: Chic Family Home in Boutique Town
Terrace/patio

Hot tub on water, 5min HITS, 20mi to Hunter skiing

Hot tub on water, 5min HITS, 20mi to Hunter skiing
Malden
10.0 out of 10, Exceptional, (7 reviews)
"It was terrific!"
United States
Alexandra M.
The price is AU$1,267
includes taxes & fees
23 June - 24 June
Hot tub on water, 5min HITS, 20mi to Hunter skiing
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 AU$518
includes taxes & fees
23 June - 24 June
rural, serene + sophisticated space
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 AU$518
includes taxes & fees
23 June - 24 June
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Smart TV

Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking

Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking
Catskill
10.0 out of 10, Exceptional, (1 review)
"Very clean; loved the spacious living room/kitchen/ dining area. Hope to stay here again. "
United States
Anonymous traveller
The price is AU$603
includes taxes & fees
23 June - 24 June
Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking
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

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

10/10 Excellent
"Very nice property right in downtown Hudson. Rooms are small but cute and with all amenities."
Robert 2-night trip
Posted 1 hour ago
Pocketbook Hotel and Bath

Find out more about Hillsdale

Hillsdale Holiday Homes information

Number of reviews
182
Accommodation
646 Holiday Homes
Lowest Price
AU$204
Highest Price
AU$1,267