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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Hillsdale holiday homes

A two-story house with a front porch, surrounded by lush greenery and trees.

1. Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam
Hillsdale
8.4 out of 10, Very good, (5 reviews)
"Overall a very pleasant stay. It is a cool old house with all its charm and quirks. Very spacious, comfortable. Decent kitchen. Location very accessible for mountains and tooling around. Just right for a getaway"
United States
Annetta D.
The price is £593
includes taxes & fees
11 Oct - 12 Oct
Perfect House In Hillsdale, Brings Friends & Fam
A two-story house with a balcony, a deck, and a view of the surrounding forest.

2. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (134 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is £569
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

3. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is £254
includes taxes & fees
26 Oct - 27 Oct
Home in Great Barrington
A wooden deck with a staircase leading to a covered porch area.

4. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (37 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is £110
includes taxes & fees
12 Oct - 13 Oct
All the comforts of home
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

5. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is £263
includes taxes & fees
13 Oct - 14 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

6. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is £334
includes taxes & fees
12 Oct - 13 Oct
Cheerful 3-bedroom cottage with woodstove
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

7. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is £243
includes taxes & fees
4 Oct - 5 Oct
Leaf-Peeper Paradise in the Berkshires
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

8. 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, (9 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 £995
includes taxes & fees
4 Oct - 5 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A camping setup with a metal chair and a table by a river in a forest.

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (15 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is £259
includes taxes & fees
15 Oct - 16 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

10. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is £531
includes taxes & fees
19 Oct - 20 Oct
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A single-story house with a porch, a chimney, and a well-maintained lawn.

11. Country House offers 2 bedrooms and a den, lots of parking.

Country House offers 2 bedrooms and a den, lots of parking.
Saugerties
The price is £245
includes taxes & fees
3 Oct - 4 Oct
Country House offers 2 bedrooms and a den, lots of parking.
A wooden cabin with a door open to a sandy beach, a sign reading "Ditch House," and a view of a lake and forest in the background.

12. Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren

Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is £363
includes taxes & fees
14 Oct - 15 Oct
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

13. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is £161
includes taxes & fees
4 Oct - 5 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

14. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is £176
includes taxes & fees
5 Oct - 6 Oct
1800s Carriage house in Berkshires / Hudson Valley
A kitchen with a central island, bar stools, and pendant lighting.

15. Cozy Catskill Escape

Cozy Catskill Escape
Catskill
10.0 out of 10, Exceptional, (2 reviews)
"Very accommodating host. Great with last minute visits."
United States
Kevin P.
The price is £210
includes taxes & fees
5 Oct - 6 Oct
Cozy Catskill Escape
A wooden deck leading to a cabin with a window and a door, surrounded by trees.

16. Modern cabin retreat

Modern cabin retreat
Catskill
The price is £223
includes taxes & fees
4 Oct - 5 Oct
Modern cabin retreat
A cabin with a large deck, multiple windows, and a fire pit.

17. Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (12 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 £264
includes taxes & fees
28 Oct - 29 Oct
Modern Luxurious Cabin, Catskills - The Tiny Nook
A modern building with a wooden deck and a door.

18. 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, (5 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 £453
includes taxes & fees
5 Oct - 6 Oct
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A spacious room with a wooden ceiling, large windows, and a chandelier.

19. Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is £557
includes taxes & fees
5 Oct - 6 Oct
Luxury Barn Retreat — All-Season Escape Awaits!
A living room with a white armchair, a grey sofa, a large green plant, and a wooden coffee table. A staircase with white railings leads to an upper floor.

20. Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties

Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties
Saugerties
10.0 out of 10, Exceptional, (3 reviews)
"Very comfortable accommodation, beds and pillows are wonderful!"
United States
Danita K.
The price is £385
includes taxes & fees
28 Oct - 29 Oct
Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties
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
"Lots of space. Very comfy beds. Toilet was really short though! Didn't use kitchen at all but looked great."
Susan 5-night trip
Posted 2 hours ago
Berkshire Mountain Lodge

Find out more about Hillsdale

Hillsdale Holiday Homes information

Number of reviews
367
Accommodation
642 Holiday Homes
Lowest Price
£110
Highest Price
£995