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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Hillsdale holiday homes

A two-story house with a balcony, a deck, and a view of the surrounding forest.

1. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (133 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.
Gorgeous Mountain Views Retreat: Family & Nature
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

2. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (26 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 AU$440
includes taxes & fees
25 Sept - 26 Sept
Riverside Retreat in the Berkshires
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

3. 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 AU$1,048
includes taxes & fees
28 Sept - 29 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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.

4. 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, (7 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 AU$1,833
includes taxes & fees
30 Sept - 1 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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 AU$606
includes taxes & fees
12 Oct - 13 Oct
Cheerful 3-bedroom cottage with woodstove
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

6. 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 AU$467
includes taxes & fees
24 Sept - 25 Sept
Home in Great Barrington
A camping setup with a metal chair and a table by a river in a forest.

7. 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 AU$466
includes taxes & fees
27 Sept - 28 Sept
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

8. 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, (40 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveller
The price is AU$1,172
includes taxes & fees
2 Oct - 3 Oct
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

9. 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 AU$819
includes taxes & fees
28 Sept - 29 Sept
Treetop Hideaway in Tyringham
A modern building with a wooden deck and a door.

10. 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 AU$835
includes taxes & fees
24 Sept - 25 Sept
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A spacious room with a wooden ceiling, large windows, and a chandelier.

11. 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 AU$1,035
includes taxes & fees
28 Sept - 29 Sept
Luxury Barn Retreat — All-Season Escape Awaits!
A wooden deck with a staircase leading to a covered porch area.

12. 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 AU$201
includes taxes & fees
5 Oct - 6 Oct
All the comforts of home
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

13. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is AU$949
includes taxes & fees
28 Sept - 29 Sept
Chic Barn Style * Fireplace * Near Stissing House
A modern kitchen with a central island, built-in appliances, and a dining area with a round table.

14. 2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Stottville
The price is AU$1,081
includes taxes & fees
28 Sept - 29 Sept
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
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.

15. 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 AU$658
includes taxes & fees
14 Oct - 15 Oct
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
A wooden deck with a wicker sofa, a hammock, and a grill.

16. Larkspire I Sleepy Hollow Lake I Beach & Firepit

Larkspire I Sleepy Hollow Lake I Beach & Firepit
Athens
10.0 out of 10, Exceptional, (1 review)
"Great property, very nice and updated, also good location at the lake"
United States
Dan K.
The price is AU$793
includes taxes & fees
20 Oct - 21 Oct
Larkspire I Sleepy Hollow Lake I Beach & Firepit
A couple in a hot tub with a natural landscape in the background.

17. 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, (10 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 AU$490
includes taxes & fees
20 Oct - 21 Oct
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

18. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is AU$1,196
includes taxes & fees
18 Oct - 19 Oct
Stylish Mid-century Modern Berkshires Cape
A kitchen with a central island, bar stools, and pendant lighting.

19. 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 AU$441
includes taxes & fees
7 Oct - 8 Oct
Cozy Catskill Escape
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
"Kudos to the welcoming and attentive staff. Fast check-in, clean suite, convenient laundry room, quiet area, and less than a 10 minute drive to Tanglewood and restaurants. Hot tub was unavailable but the beverage machine at the lobby was very much appreciated."
L 2-night trip
Posted less than an hour ago
Berkshire Mountain Lodge

Find out more about Hillsdale

Hillsdale Holiday Homes information

Number of reviews
390
Accommodation
618 Holiday Homes
Lowest Price
AU$201
Highest Price
AU$1,833