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 Sept - 6 Sept
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 cottages

A kitchen with white cabinetry, granite countertops, and a window with blinds.

1. Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (13 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
The price is AU$336
includes taxes & fees
9 Sept - 10 Sept
Charming loft cottage in tranquil Germantown with WiFi, AC
A single-story house with a black front door, two windows on either side, and two black trash bins in front.

2. Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (24 reviews)
"Everything was great! The house is in a great location and is very clean, modern and cozy. I would highly recommend staying here! "
United States
Dave P.
The price is AU$490
includes taxes & fees
24 Aug - 25 Aug
Charming Cottage in the Heart of Catskill & Pet Friendly
A covered porch with a wooden bench, a wicker chair, and a sofa with cushions.

3. Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.8 out of 10, Exceptional, (19 reviews)
"Host was super welcoming - the pace was gorgeous and had everything we could possibly need! Fabulous stay overall"
United States
Athena P.
The price is AU$434
includes taxes & fees
23 Sept - 24 Sept
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
A single-story house with a dark exterior, a chimney, and a small window.

4. Cozy 2-bedroom cottage in enchanting Catskill Mountains

Cozy 2-bedroom cottage in enchanting Catskill Mountains
Catskill
10.0 out of 10, Exceptional, (1 review)
"The property is great. Easy check-in and communication with host. Large property and comfortable beds."
United States
Robert G.
The price is AU$709
includes taxes & fees
24 Aug - 25 Aug
Cozy 2-bedroom cottage in enchanting Catskill Mountains
A cabin with a wooden deck, a covered porch, and a gravel driveway.

5. 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 AU$773
includes taxes & fees
24 Aug - 25 Aug
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A two-story house with a balcony, a chimney, and a window with a view.

6. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is AU$2,750
includes taxes & fees
22 Sept - 23 Sept
Berkshires farm, 30+ guests, 50 acres
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

The Whitlock

The Whitlock

8/10 Good
"This is a very quaint hotel in a fantastic location. It is easy to walk to everything in Lenox and even Tanglewood from the hotel. Just be aware it is an uphill walk back from Tanglewood. The room was very spacious and bed very comfortable. Would definitely stay here again. If looking for any opportunities to improve, only thing I can come up with is a small frig in the room. Great place!"
Patricia 1-night trip
Posted 9 hours ago
The Whitlock

Find out more about Hillsdale

Hillsdale Cottages information

Number of reviews
33
Accommodation
159 Cottages
Lowest Price
AU$336
Highest Price
AU$2,750

Frequently asked questions

What is there to do in Hillsdale near my cottage?
Once you've unpacked your bags and settled in, head out and discover the fantastic things Hillsdale has for you to experience. Catamount Aerial Adventure Park is a great attraction to add to your itinerary.