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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Hillsdale cottages

A kitchen with a central island, white cabinetry, a stove, and a sink. There is a staircase leading to another level.

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, (17 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
The price is €222
includes taxes & fees
16 Nov - 17 Nov
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, (31 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 €322
includes taxes & fees
15 Nov - 16 Nov
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, (21 reviews)
"Artsy, comfortable and cozy cottage in a country setting. Love the deck for grilling! This was our second time here and we hope to be back again!"
United States
Laura G.
The price is €293
includes taxes & fees
16 Nov - 17 Nov
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
A wooden deck with a glass table and chairs, an umbrella, and a view of autumn trees.

4. 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 €532
includes taxes & fees
15 Nov - 16 Nov
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

5. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
The price is €412
includes taxes & fees
15 Nov - 16 Nov
Sharon Retreat w/ Private Yard
A single-story house with a dark exterior, a chimney, and a small window.

6. Cozy 2-bedroom cottage in enchanting Catskill Mountains

Cozy 2-bedroom cottage in enchanting Catskill Mountains
Catskill
10.0 out of 10, Exceptional, (2 reviews)
"The property is great. Easy check-in and communication with host. Large property and comfortable beds."
United States
Robert G.
The price is €440
includes taxes & fees
16 Nov - 17 Nov
Cozy 2-bedroom cottage in enchanting Catskill Mountains
A white single-story house with a front porch, surrounded by trees with autumn foliage.

7. 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 €1,874
includes taxes & fees
14 Dec - 15 Dec
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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Learn more about Hillsdale

Tucked in the Hudson Valley, this rural hamlet offers scenic hikes through Taconic State Park and charming farm-to-table dining. Explore nearby art galleries in Copake or visit Catamount Mountain Resort for outdoor adventures in all seasons.

See all hotels in Hillsdale
A landscape with a row of trees in autumn colors, a wooden fence, and a hilly background.

Frequently Asked Questions

Why book your cottage in Hillsdale with Expedia?

We think that holidays 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.