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

Hillsdale Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Hillsdale vacation rentals

Outdoor dining

1. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is P13,519
P15,141 total
includes taxes & fees
Aug 25 - Aug 26
Gatherwild Ranch
Exterior

2. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (168 reviews)
"Clean, quiet and relaxing stay."
United States
Andrea
The price is P8,329
P9,328 total
includes taxes & fees
Aug 18 - Aug 19
Micosta Leisure Inn
Lobby

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,077 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is P5,813
P7,866 total
includes taxes & fees
Aug 31 - Sep 1
Berkshire Mountain Lodge
Interior

4. Mtn-view Retreat in Huson Valley: Great for Groups

Mtn-view Retreat in Huson Valley: Great for Groups
3.0 star property
Hudson
The price is P15,854
P46,802 total
includes taxes & fees
Aug 21 - Aug 22
Mtn-view Retreat in Huson Valley: Great for Groups
Exterior

5. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (274 reviews)
"Very clean, supplied burning wood, parking, WiFi, very cozy and comfortable"
United States
Enior
The price is P9,893
P13,339 total
includes taxes & fees
Sep 16 - Sep 17
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Front of property

6. Sleepy Hollow Lake Home w/ Deck, Pool Access!

Sleepy Hollow Lake Home w/ Deck, Pool Access!
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (2 reviews)
"The house was convenient to our friend’s wedding venue. It was spacious, clean and comfortable! There were many great amenities that we didn’t have time use due to our schedule and rainy weather."
United States
audrey
The price is P18,619
P36,346 total
includes taxes & fees
Aug 19 - Aug 20
Sleepy Hollow Lake Home w/ Deck, Pool Access!
Interior

7. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is P13,765
P34,053 total
includes taxes & fees
Aug 24 - Aug 25
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Hillsdale Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Pleasant stay and Sarah made a bouquet of flowers for my daughter’s birthday..a fellow Leo!"
Marion 1-night trip
Posted 11 hours ago
Berkshires Untold

Find out more about Hillsdale

Search for holiday rentals in Hillsdale on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillsdale using one of the methods below:

  • View our selection of featured holiday rentals in Hillsdale
  • Use the map to find apartments and other holiday homes in the Hillsdale neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Hillsdale while they last

Look no further and take a look at our great range of rental properties in Hillsdale!

Frequently asked questions

Can I find a vacation rental in Hillsdale?

Yes, we have vacation rentals close to the most popular attractions in Hillsdale, or you can go with a more remote option if you'd like a relaxing place to stay. Hillsdale is known for its coffeehouses and ski areas.

How many vacation rentals are there in Hillsdale?

With 46 Expedia vacation rentals, you're sure to find just the right place for your Hillsdale stay.

What’s there to see and do in Hillsdale?

Copake Lake and Mosquito Island are a couple of lovely local spots to get outside and enjoy nature. While here, Catamount Aerial Adventure Park and Catamount Ski Area are other places worth a visit.

What’s a vacation rental in Hillsdale like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Hillsdale. Vacation rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for families.