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

Search Hillsdale Cottage Rentals from CA $334

  • 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 cottages

A wooden deck with a railing, a blue exterior wall, and a yellow door.

1. 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 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 CA $248
CA $492 total
includes taxes & fees
Aug 24 - Aug 25
Charming Cottage in the Heart of Catskill & Pet Friendly
A kitchen with white cabinetry, granite countertops, and a window with blinds.

3. 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 CA $182
CA $334 total
includes taxes & fees
Sep 9 - Sep 10
Charming loft cottage in tranquil Germantown with WiFi, AC
A covered porch with a wooden bench, a wicker chair, and a sofa with cushions.

4. 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, (18 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 CA $185
CA $438 total
includes taxes & fees
Sep 14 - Sep 15
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
A single-story house with a dark exterior, a chimney, and a small window.

5. 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 CA $331
CA $703 total
includes taxes & fees
Aug 24 - Aug 25
Cozy 2-bedroom cottage in enchanting Catskill Mountains
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 CA $1,552
CA $3,011 total
includes taxes & fees
Sep 9 - Sep 10
Berkshires farm, 30+ guests, 50 acres
A cabin with a wooden deck, a covered porch, and a gravel driveway.

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 CA $309
CA $764 total
includes taxes & fees
Aug 29 - Aug 30
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"."
Mark 3-night trip
Posted 8 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Hillsdale

Hillsdale Cottages information

Number of reviews
32
Accommodation
154 Cottages
Lowest Price
CA $334
Highest Price
CA $3,011

Frequently asked questions

Why book your cottage in Hillsdale with Expedia?
We think that vacations should be easy, so if you're looking for cottages in Hillsdale at an affordable rate, Expedia has got your back. Keep the budget under control and check in to an inexpensive option far away from the city rush, or splurge on a 5-star cottage to treat your loved ones.
How can I find cheap cottages in Hillsdale?
The quickest way to score cheap cottages in Hillsdale is with Expedia's user-friendly filter tool. Refine your search results by star rating, budget and amenities to take advantage of awesome rates with only a few clicks.
What is there to do in Hillsdale near my cottage?
The ideal travel accessory is a well-thought-out travel plan. Catamount Aerial Adventure Park is a wonderful spot to kick off your exploration of Hillsdale.

Explore a world of travel with Expedia