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 39 Rentals in the Hillsdale Area
loading...
From
$461
Per Night
Hillsdale
3 Bedrooms, 2 Bathrooms, Sleeps 13
Booking
18 photos Details
Reviews (1) Make Enquiry
From
$163
Per Night
Hillsdale
4 Bedrooms, 3 Bathrooms, Sleeps 7
Booking
45 photos Details
Reviews (1) Make Enquiry
From
$109
Per Night
Hillsdale
2 Bedrooms, 1 Bathroom, Sleeps 3
10 photos Details
Make Enquiry
From
$190
Per Night
Hillsdale
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
30 photos Details
Make Enquiry
From
$109
Per Night
Hillsdale
3 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details
Reviews (4) Make Enquiry
From
$163
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
$217
Per Night
Copake
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
14 photos Details
Reviews (1) Make Enquiry
From
$136
Per Night
Ancram
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
19 photos Details
Reviews (1) Make Enquiry
From
$814
Per Week
Copake
3 Bedrooms, 1 Bathroom, Sleeps 6
4 photos Details
Reviews (1) Make Enquiry
From
$201
Per Night
Alford, MA
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
12 photos Details
Reviews (3) Make Enquiry
Get the List
From
$543
Per Night
Sheffield, MA
4 Bedrooms, 3 Bathrooms, Sleeps 15
19 photos Details
Reviews (8) Make Enquiry
From
$212
Per Night
Great Barrington, MA
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
10 photos Details
Reviews (9) Make Enquiry
From
$174
Per Night
North Egremont, MA
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
35 photos Details
Reviews (3) Make Enquiry
From
$271
Per Night
Great Barrington, MA
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
10 photos Details
Reviews (2) Make Enquiry
From
$271
Per Night
Austerlitz
4 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
12 photos Details
Reviews (3) Make Enquiry
From
$4,885
Per Week
Great Barrington, MA
6 Bedrooms, 6 Bathrooms, Sleeps 12
25 photos Details
Make Enquiry
From
$380
Per Night
Great Barrington, MA
5 Bedrooms, 3 Bathrooms, Sleeps 11
9 photos Details
Make Enquiry
From
$380
Per Night
Austerlitz
2 Bedrooms, 2 Bathrooms, Sleeps 4
12 photos Details
Make Enquiry
From
$217
Per Night
Austerlitz
3 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
18 photos Details
Make Enquiry
From
$868
Per Night
Ancram
5 Bedrooms, 4 Bathrooms, Sleeps 12
13 photos Details
Make Enquiry
From
$326
Per Night
Great Barrington, MA
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
23 photos Details
Make Enquiry
From
$505
Per Night
Great Barrington, MA
5 Bedrooms, 4 Bathrooms, Sleeps 10
Booking
27 photos Details
Make Enquiry
From
$217
Per Night
Great Barrington, MA
4 Bedrooms, 3 Bathrooms, Sleeps 10
15 photos Details
Make Enquiry
From
$217
Per Night
Great Barrington, MA
2 Bedrooms, 2 Bathrooms, Sleeps 4
10 photos Details
Make Enquiry
From
$516
Per Night
Great Barrington, MA
4 Bedrooms, 6 Bathrooms, Sleeps 12
22 photos Details
Make Enquiry
From
$326
Per Night
Great Barrington, MA
4 Bedrooms, 2 Bathrooms, Sleeps 9
Booking
11 photos Details
Make Enquiry
From
$217
Per Night
Great Barrington, MA
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
10 photos Details
Make Enquiry
From
$2,171
Per Night
Ancram
5 Bedrooms, 6 Bathrooms, Sleeps 12
20 photos Details
Make Enquiry
From
$163
Per Night
Craryville
2 Bedrooms, 3 Bathrooms, Sleeps 6
6 photos Details
Make Enquiry
From
$1,357
Per Week
Copake
3 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (2) Make Enquiry
From
$624
Per Night
Great Barrington, MA
4 Bedrooms, 3 Bathrooms, Sleeps 10
33 photos Details
Reviews (3) Make Enquiry
From
$570
Per Night
Sheffield, MA
4 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details
Reviews (16) Make Enquiry
From
$190
Per Night
Copake
3 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
16 photos Details
Reviews (5) Make Enquiry
From
$172
Per Night
Great Barrington, MA
5 Bedrooms, 5 Bathrooms, Sleeps 10
20 photos Details
Make Enquiry
From
$140
Per Night
Copake
3 Bedrooms, 2 Bathrooms, Sleeps 6
1 photo Details
Make Enquiry
From
$271
Per Night
Great Barrington, MA
3 Bedrooms, 2 Bathrooms, Sleeps 8
19 photos Details
Make Enquiry
From
$326
Per Night
Great Barrington, MA
4 Bedrooms, 2 Bathrooms, Sleeps 11
13 photos Details
Make Enquiry
From
$326
Per Night
Housatonic, MA
4 Bedrooms, 3 Bathrooms, Sleeps 10
9 photos Details
Make Enquiry
From
$290
Per Night
South Egremont, MA
4 Bedrooms, 2 Bathrooms, Sleeps 8
5 photos Details
Make Enquiry
Go to map view
Book Online(29)
Use filters to find the best results!

Suitability

  • Wheelchair access (0)
  • Elder access (20)
  • Suitable for children (26)
  • Pet friendly (15)
  • Smoking allowed (1)

Amenities

  • Internet (35)
  • Other outdoor space (35)
  • Grill (29)
  • Parking (26)
  • Air Conditioning (24)
  • 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