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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Hillsdale holiday homes

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

1. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (40 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is €307
includes taxes & fees
3 Nov - 4 Nov
Home in Great Barrington
A wooden deck with a staircase leading to a covered porch area.

2. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"No frills, very clean and peaceful, beautiful setting"
United States
Lori M.
The price is €130
includes taxes & fees
1 Nov - 2 Nov
All the comforts of home
A staircase with a wooden handrail and a white wall with a light switch.

3. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 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 €253
includes taxes & fees
26 Oct - 27 Oct
Leaf-Peeper Paradise in the Berkshires
A camping setup with a metal chair and a table by a river in a forest.

4. 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, (16 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 €303
includes taxes & fees
22 Oct - 23 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

5. 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 €390
includes taxes & fees
2 Nov - 3 Nov
Cheerful 3-bedroom cottage with woodstove
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

6. 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 €313
includes taxes & fees
22 Oct - 23 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
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.

7. 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 €1,180
includes taxes & fees
22 Oct - 23 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is €614
includes taxes & fees
16 Nov - 17 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A modern interior with a staircase, wooden flooring, a dining area, and a brick wall.

9. Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (31 reviews)
"Fantastic place way better than expected."
United States
Robert H.
Catskill Cottage Walk to Downtown & River Views
A wooden dresser with a mirror above it, a lamp on top, and a vase with flowers on the dresser.

10. Hudson Retreat - 1780s Renovated Barn

Hudson Retreat - 1780s Renovated Barn
Hudson
10.0 out of 10, Exceptional, (2 reviews)
"The house is beyond beautiful! The host was very accommodating and readily available for any questions. We stayed with our toddler and friends and it was perfect for everyone. "
United States
Julie L.
Hudson Retreat - 1780s Renovated Barn
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

11. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is €585
includes taxes & fees
22 Oct - 23 Oct
Secluded Family Home in Serene Stockbridge Woods
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

12. 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)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is €192
includes taxes & fees
27 Oct - 28 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

13. 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 €201
includes taxes & fees
5 Nov - 6 Nov
1800s Carriage house in Berkshires / Hudson Valley
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.

14. 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 €406
includes taxes & fees
27 Oct - 28 Oct
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
A cabin with a large deck, multiple windows, and a fire pit.

15. Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (14 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 €311
includes taxes & fees
9 Nov - 10 Nov
Modern Luxurious Cabin, Catskills - The Tiny Nook
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 €255
includes taxes & fees
17 Nov - 18 Nov
Modern cabin retreat
A cozy living room with a sofa, a fireplace, and large windows.

17. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is €623
includes taxes & fees
27 Oct - 28 Oct
Luxury Barn Near Hudson With New Private Sauna
A dining area with a chandelier, wooden chairs, a table, and a view through a glass door.

18. Creek Views * Chef’s Kitchen * Walk To Lighthouse

Creek Views * Chef’s Kitchen * Walk To Lighthouse
Saugerties
9.8 out of 10, Exceptional, (7 reviews)
"this house was very comfortable and convenient to Saugerties"
United States
molly f.
The price is €527
includes taxes & fees
16 Nov - 17 Nov
Creek Views * Chef’s Kitchen * Walk To Lighthouse
A couple in a hot tub with a natural landscape in the background.

19. 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, (12 reviews)
"Beautiful house and wonderful host. I very much hope we get to stay again in the future. "
United States
Jeffrey D.
The price is €513
includes taxes & fees
26 Oct - 27 Oct
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
A modern living space with a kitchen area, a dining table, and a sofa.

20. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is €265
includes taxes & fees
17 Nov - 18 Nov
Cabin Oasis near Town
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"I needed to stay here for work. Hotel met and exceeded all my needs."
Matthew 1-night trip
Posted less than an hour ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Hillsdale

Hillsdale Holiday Homes information

Number of reviews
269
Accommodation
629 Holiday Homes
Lowest Price
€130
Highest Price
€1,180