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

Hillsdale Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Hillsdale holiday rentals

Outdoor dining

1. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is S$281
includes taxes & fees
10 Aug - 11 Aug
Gatherwild Ranch
Exterior

2. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (163 reviews)
"This inn with cabins is a gorgeous setting with a nice vegetable garden, the setting is a bit remote and we like it, very quiet, unfortunately the restaurant was close."
United States
philippe
The price is S$192
includes taxes & fees
9 Aug - 10 Aug
Micosta Leisure Inn
Lobby

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,043 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is S$191
includes taxes & fees
23 Aug - 24 Aug
Berkshire Mountain Lodge
Exterior

4. 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, (266 reviews)
"Very clean, supplied burning wood, parking, WiFi, very cozy and comfortable"
United States
Enior
The price is S$331
includes taxes & fees
10 Aug - 11 Aug
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Interior

5. 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 S$949
includes taxes & fees
9 Aug - 10 Aug
Mtn-view Retreat in Huson Valley: Great for Groups
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
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 S$710
includes taxes & fees
9 Aug - 10 Aug
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.
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Top Hillsdale Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

8/10 Good
"Stayed for two nights in a 2 bedroom villa. The place was very clean, beds and bedding were comfortable. The place could stand a refresh - more so the kitchen and bathrooms but not terribly awful by any means. The area of the property where we stayed was quiet and peaceful."
elizabeth 2-night trip
Posted 11 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Frequently asked questions

Can I find a holiday rental in Hillsdale?

Yes, there are holiday rentals close to the most popular sights in Hillsdale, or you can select a more secluded option if you're looking for a relaxing stay. Hillsdale is known for its coffee shops and ski areas.

How many holiday rentals are there in Hillsdale?

With 49 Expedia holiday rentals, you're guaranteed 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 holiday rental in Hillsdale like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hillsdale. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for families.