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

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Check prices for these dates

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

Our top choices for Hillsdale holiday rentals

A tented area with two wooden folding chairs and a table, a patterned rug, and a view of greenery and a white tent in the background.

1. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is 6.461.482 ₫
7.236.862 ₫ total
includes taxes & fees
15 Sept - 16 Sept
Gatherwild Ranch
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

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 3.387.039 ₫
3.793.861 ₫ total
includes taxes & fees
27 Aug - 28 Aug
Micosta Leisure Inn
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,084 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is 2.476.432 ₫
3.351.012 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge

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

Mtn-view Retreat in Huson Valley: Great for Groups
3.0 star property
Hudson
Mtn-view Retreat in Huson Valley: Great for Groups
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

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, (278 reviews)
"Beautiful place"
United States
Kevin
The price is 4.203.227 ₫
5.667.307 ₫ total
includes taxes & fees
21 Sept - 22 Sept
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A deck with wicker furniture and a glass door leading to a covered patio.

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!
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

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 5.847.968 ₫
14.467.455 ₫ total
includes taxes & fees
2 Sept - 3 Sept
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 & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"."
Mark 3-night trip
Posted 6 hours ago
Holiday Inn & Suites Pittsfield-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 46 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.