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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Hillsdale holiday rentals

Exterior

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,253 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is ฿2,788
฿3,868 total
includes taxes & fees
3 Dec - 4 Dec
Berkshire Mountain Lodge
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, (194 reviews)
"Great stay"
United States
George
The price is ฿3,334
฿3,735 total
includes taxes & fees
4 Nov - 5 Nov
Micosta Leisure Inn
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

3. 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, (335 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
The price is ฿5,134
฿7,004 total
includes taxes & fees
2 Dec - 3 Dec
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A cozy living room with green sofas, a wooden ceiling, and a large window.

4. Maya's Garden House

Maya's Garden House
2.0 star property
Great Barrington
The price is ฿30,064
฿42,431 total
includes taxes & fees
4 Dec - 5 Dec
Maya's Garden House
A cabin with a triangular window, wooden walls, and a bed with pillows.

5. Gather Greene

Gather Greene
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (5 reviews)
"The room was spotless and very cozy! Everything was perfect, the scenery the smell, the atmosphere…EVRYTHING! The staff on the property were extremely friendly and generously helpful! Would 100% recommend for a couple’s getaway! Parking wasn’t a problem at all as well! Short walking distance to the cabins and back."
United States
Jabari
The price is ฿9,255
฿9,995 total
includes taxes & fees
20 Nov - 21 Nov
Gather Greene
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.

6. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is ฿7,524
฿9,184 total
includes taxes & fees
4 Nov - 5 Nov
Gatherwild Ranch
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 ฿8,564
฿19,807 total
includes taxes & fees
17 Nov - 18 Nov
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

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"very centrally located, convenient"
Sheri 1-night trip
Posted 2 hours ago
Quality Inn Lee - Lenox South

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

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.