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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Hillsdale holiday homes

Exterior

Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (129 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 €631
includes taxes & fees
9 Aug - 10 Aug
Gorgeous Mountain Views Retreat: Family & Nature
TV, fireplace, printers

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, (6 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 €1,168
includes taxes & fees
28 Jul - 29 Jul
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (19 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is €304
includes taxes & fees
26 Jul - 27 Jul
Cozy Riverside Berkshires Retreat
TV, fireplace, DVD player, books

Mtn-View Retreat in Huson Valley: Great for Groups

Mtn-View Retreat in Huson Valley: Great for Groups
Claverack
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful rental - spacious, beautiful views, and gorgeous home!"
United States
Samantha A.
The price is €664
includes taxes & fees
23 Jul - 24 Jul
Mtn-View Retreat in Huson Valley: Great for Groups
Coffee/tea maker, fridge, microwave, oven

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (34 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is €363
includes taxes & fees
29 Jul - 30 Jul
Home in Great Barrington
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (7 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 €427
includes taxes & fees
3 Aug - 4 Aug
Sweet Cozy Victorian in Housatonic. Close to everything.
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, (9 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is €336
includes taxes & fees
28 Jul - 29 Jul
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
TV, fireplace, stereo

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, Cabin Sleeps 14, Walk To Town
Great Barrington
9.6 out of 10, Exceptional, (50 reviews)
"The host was wonderful and the place was amazing!"
United States
James M.
The price is €2,144
includes taxes & fees
2 Aug - 3 Aug
Great Barrington, Cabin Sleeps 14, Walk To Town
Pool

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, (8 reviews)
"Our host was fantastic! She allowed us to check in early and check out late. The house was cozy and perfect for my girls weekend! "
United States
Kim W.
The price is €492
includes taxes & fees
23 Jul - 24 Jul
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Exterior detail

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
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 €384
includes taxes & fees
30 Jul - 31 Jul
Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Property grounds

Lakefront Summer Stunner in New England Just 2 Hours From NYC

Lakefront Summer Stunner in New England Just 2 Hours From NYC
Sharon
10.0 out of 10, Exceptional, (95 reviews)
"Great location, quiet and beautiful. Loved the trails, picturesque drives between small towns and cozy accommodations. "
United States
Chad J.
The price is €536
includes taxes & fees
25 Jul - 26 Jul
Lakefront Summer Stunner in New England Just 2 Hours From NYC
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.
rural, serene + sophisticated space
TV, fireplace, books

NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
10.0 out of 10, Exceptional, (2 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 €822
includes taxes & fees
27 Jul - 28 Jul
NEW: Chic Modern Barn Style Home in Fun Area
TV

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 €605
includes taxes & fees
28 Jul - 29 Jul
Treetop Hideaway in Tyringham
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 €509
includes taxes & fees
11 Aug - 12 Aug
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Desk, WiFi

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is €480
includes taxes & fees
23 Jul - 24 Jul
Charles Cottage Near Warren St New Renovation
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (34 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is €128
includes taxes & fees
23 Jul - 24 Jul
All the comforts of home
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"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 €381
includes taxes & fees
4 Aug - 5 Aug
stylish Berkshires Retreat
Coffee/tea maker, fridge, microwave, oven

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 €715
includes taxes & fees
6 Aug - 7 Aug
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
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 €361
includes taxes & fees
27 Jul - 28 Jul
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"I liked the gym, bed, pillows, TV stations selections. I didn't like the location of the room safe which was literally floor level and practically impossible to access. The couch in our room seemed to be missing a cushion to allow one to rest against."
Brian 1-night trip
Posted 10 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Hillsdale

Hillsdale Holiday Homes information

Number of reviews
438
Accommodation
664 Holiday Homes
Lowest Price
€128
Highest Price
€2,144