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

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Our top choices for Hillsdale vacation homes

1. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is ¥34,033
¥50,158 total
includes taxes & fees
Nov 9 - Nov 10
Home in Great Barrington

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 ¥16,733
¥20,859 total
includes taxes & fees
Nov 4 - Nov 5
All the comforts of home

3. 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)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is ¥31,512
¥52,271 total
includes taxes & fees
Nov 3 - Nov 4
Sweet Cozy Victorian in Housatonic. Close to everything.

4. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ¥27,935
¥64,116 total
includes taxes & fees
Nov 3 - Nov 4
Cheerful 3-bedroom cottage with woodstove

5. 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 ¥31,906
¥47,430 total
includes taxes & fees
Nov 3 - Nov 4
Leaf-Peeper Paradise in the Berkshires

6. 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, (10 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 ¥89,195
¥189,740 total
includes taxes & fees
Nov 4 - Nov 5
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is ¥63,024
¥105,069 total
includes taxes & fees
Nov 16 - Nov 17
Cozy. Clean. Free bagel shop. 3 Fireplaces.

8. Maya's Garden House

Maya's Garden House
2.0 star property
Great Barrington
The price is ¥140,492
¥198,290 total
includes taxes & fees
Nov 3 - Nov 4
Maya's Garden House

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, (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 ¥31,512
¥51,352 total
includes taxes & fees
Nov 3 - Nov 4
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.8 out of 10, Excellent, (8 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 ¥11,029
¥30,831 total
includes taxes & fees
Nov 3 - Nov 4
NEW RENO - Chalet-style farm loft near Tanglewood

11. 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 ¥13,393
¥33,372 total
includes taxes & fees
Nov 5 - Nov 6
1800s Carriage house in Berkshires / Hudson Valley

12. 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 ¥59,715
¥104,013 total
includes taxes & fees
Nov 10 - Nov 11
Secluded Family Home in Serene Stockbridge Woods

13. Modern cabin retreat

Modern cabin retreat
Catskill
The price is ¥20,806
¥38,837 total
includes taxes & fees
Nov 3 - Nov 4
Modern cabin retreat

14. Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington

Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington
Great Barrington
The price is ¥142,004
¥210,018 total
includes taxes & fees
Nov 8 - Nov 9
Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington

15. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is ¥21,901
¥42,025 total
includes taxes & fees
Dec 1 - Dec 2
Cabin Oasis near Town

16. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
The price is ¥122,109
¥206,202 total
includes taxes & fees
Nov 9 - Nov 10
Beautiful and Private Home Centrally Located in the Berkshires

17. 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 ¥32,300
¥68,725 total
includes taxes & fees
Dec 1 - Dec 2
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren

18. 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 ¥60,267
¥102,087 total
includes taxes & fees
Nov 3 - Nov 4
Luxury Barn Near Hudson With New Private Sauna

19. 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 ¥21,665
¥91,853 total
includes taxes & fees
Nov 15 - Nov 16
Creek Views * Chef’s Kitchen * Walk To Lighthouse

20. 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 ¥22,689
¥43,676 total
includes taxes & fees
Nov 30 - Dec 1
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

Find out more about Hillsdale

Hillsdale Vacation Homes information

Number of reviews
216
Accommodation
629 Vacation Homes
Lowest Price
¥20,859
Highest Price
¥189,740