We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation rentals in Hillsdale, NY and nearby

Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 36 Rentals in the Hillsdale Area
loading...
From
$480
Per Night
Hillsdale
3 Bedrooms, 2 Bathrooms, Sleeps 13
Booking
18 photos Details Reviews (1) Make Enquiry
From
$169
Per Night
Hillsdale
4 Bedrooms, 3 Bathrooms, Sleeps 7
Booking
45 photos Details Reviews (2) Make Enquiry
From
$113
Per Night
Hillsdale
2 Bedrooms, 1 Bathroom, Sleeps 3
10 photos Details Make Enquiry
From
$198
Per Night
Hillsdale
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
30 photos Details Make Enquiry
From
$113
Per Night
Hillsdale
3 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details Reviews (4) Make Enquiry
From
$169
Per Night
Hillsdale
3 Bedrooms, 3 Bathrooms, Sleeps 8
8 photos Details Make Enquiry

The following rentals are within 15 kilometres of Hillsdale, New York.

From
$209
Per Night
Alford, MA
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
12 photos Details Reviews (3) Make Enquiry
From
$226
Per Night
Copake
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
14 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 6 February 2014
The home fit all 5 of my guests comfortably. It was centrally located to skiing and was a wonderful home and a very cozy experience
See all reviews
From
$846
Per Week
Copake
3 Bedrooms, 1 Bathroom, Sleeps 6
4 photos Details Reviews (1) Make Enquiry
From
$181
Per Night
North Egremont, MA
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
35 photos Details Reviews (5) Make Enquiry
5 of 5 stars Reviewed 11 September 2014
I had a wonderful stay! The property is gorgeous and serene. The suite is clean, very nicely decorated and private. Absolutely lovely!
5 of 5 stars Reviewed 4 September 2014
Lovely haven in the bucolic Berkshire countryside . Our suite had everything we could want- privacy, beautiful restful decor, comfort , all in a gorgeous setting. Short drive to...
See all reviews
Get the List
From
$141
Per Night
Ancram
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
19 photos Details Reviews (1) Make Enquiry
From
$564
Per Night
Sheffield, MA
4 Bedrooms, 3 Bathrooms, Sleeps 15
19 photos Details Reviews (8) Make Enquiry
5 of 5 stars Reviewed 6 August 2014
Casey's place was really lovely - just exactly as described! WONDERFUL central great room/dining room for our large group to gather and relax - and beautiful decks for reading...
5 of 5 stars Reviewed 23 February 2014
Racebrook Lodge is our "home away from home", and Casey and Dave (the owners) are so incredibly hospitable. This house, their most recent addition to the property, is the GEM of...
See all reviews
From
$339
Per Night
Austerlitz
4 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
12 photos Details Reviews (3) Make Enquiry
From
$282
Per Night
Great Barrington, MA
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
10 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 20 May 2013
This was a perfect weekend for us. I am very picking when choosing a cabin rental because I want it to be "just right--" to fit into all of my ideal visions of the quintessential...
See all reviews
From
$220
Per Night
Great Barrington, MA
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
10 photos Details Reviews (9) Make Enquiry
5 of 5 stars Reviewed 17 August 2014
We stayed at the cottage for three days, and it was just as lovely as advertised. The space is perfect for a couple, with a comfortable queen bed and well-equipped kitchen...
5 of 5 stars Reviewed 22 July 2014
My wife and I were extremely lucky to find Efrem and Frederica's cottage in The Berkshires. We really enjoyed the beautiful and relaxing view that their backyard had to offer! The...
See all reviews
From
$367
Per Night
Great Barrington, MA
5 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
27 photos Details Reviews (1) Make Enquiry
3 of 5 stars Reviewed 11 September 2014
This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
See all reviews
From
$5,079
Per Week
Great Barrington, MA
6 Bedrooms, 6 Bathrooms, Sleeps 12
25 photos Details Make Enquiry
From
$395
Per Night
Great Barrington, MA
5 Bedrooms, 3 Bathrooms, Sleeps 10
9 photos Details Make Enquiry
From
$226
Per Night
Austerlitz
3 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
18 photos Details Make Enquiry
From
$339
Per Night
Great Barrington, MA
4 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
11 photos Details Make Enquiry
From
$226
Per Night
Great Barrington, MA
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
10 photos Details Make Enquiry
From
$536
Per Night
Great Barrington, MA
4 Bedrooms, 6 Bathrooms, Sleeps 12
22 photos Details Make Enquiry
From
$226
Per Night
Great Barrington, MA
2 Bedrooms, 2 Bathrooms, Sleeps 4
10 photos Details Make Enquiry
From
$395
Per Night
Austerlitz
2 Bedrooms, 2 Bathrooms, Sleeps 4
12 photos Details Make Enquiry
From
$226
Per Night
Great Barrington, MA
4 Bedrooms, 3 Bathrooms, Sleeps 10
15 photos Details Make Enquiry
From
$169
Per Night
Craryville
2 Bedrooms, 3 Bathrooms, Sleeps 6
6 photos Details Make Enquiry
From
$339
Per Night
Great Barrington, MA
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
23 photos Details Make Enquiry
From
$593
Per Night
Sheffield, MA
4 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details Reviews (16) Make Enquiry
From
$1,411
Per Week
Copake
3 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details Reviews (2) Make Enquiry
From
$649
Per Night
Great Barrington, MA
4 Bedrooms, 3 Bathrooms, Sleeps 10
33 photos Details Reviews (3) Make Enquiry
From
$198
Per Night
Copake
3 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
16 photos Details Reviews (6) Make Enquiry
5 of 5 stars Reviewed 5 September 2014
a great location tucked away yet close to all activities. The house is super comfortable and clean. Includes everything you might want, wifi internet is free and easy to access
5 of 5 stars Reviewed 24 July 2014
Had family coming from New York, Massachusetts and Connecticut to celebrate my birthday ~ hotels, motels are expensive, and they're not home. This house offered a great place to...
See all reviews
From
$282
Per Night
Great Barrington, MA
3 Bedrooms, 2 Bathrooms, Sleeps 8
19 photos Details Make Enquiry
From
$339
Per Night
Housatonic, MA
4 Bedrooms, 3 Bathrooms, Sleeps 10
9 photos Details Make Enquiry
From
$146
Per Night
Copake
3 Bedrooms, 2 Bathrooms, Sleeps 6
1 photo Details Make Enquiry
From
$212
Per Night
Great Barrington, MA
4 Bedrooms, 2 Bathrooms, Sleeps 10
12 photos Details Make Enquiry
From
$301
Per Night
South Egremont, MA
4 Bedrooms, 2 Bathrooms, Sleeps 8
5 photos Details Make Enquiry
Go to map view
Book Online(27)
Use filters to find the best results!

Suitability

  • Wheelchair access (0)
  • Elder access (18)
  • Suitable for children (25)
  • Pet friendly (13)
  • Smoking allowed (1)

Amenities

  • Internet (33)
  • Other outdoor space (33)
  • Parking (29)
  • Grill (28)
  • Washer/Dryer (26)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities