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
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Hillsdale cottages

Exterior

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

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.6 out of 10, Exceptional, (16 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 €264
includes taxes & fees
29 Jun - 30 Jun
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Exterior

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)
"Clean and cozy with great amenities! Would come back!"
United States
Kristen B.
The price is €312
includes taxes & fees
22 Jun - 23 Jun
Charming Cottage in the Heart of Catskill & Pet Friendly
House (3 Bedrooms) | Interior

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 €483
includes taxes & fees
22 Jun - 23 Jun
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Property grounds

Pet Friendly • Fenced Yard • Hot Tub • Romantic

Pet Friendly • Fenced Yard • Hot Tub • Romantic
Ravena
10.0 out of 10, Exceptional, (1 review)
"This was a very quaint cottage type home the owner was very quick with replies. Loved that it had a fenced in yard for our dog. Was scheduled to work at the hospital all weekend, so this was a nice getaway from the hustle and bustle. We’ll stay again if we are ever in the area. "
United States
Sunshine G.
The price is €310
includes taxes & fees
22 Jun - 23 Jun
Pet Friendly • Fenced Yard • Hot Tub • Romantic
Terrace/patio

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Exterior

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 €2,062
includes taxes & fees
7 Jul - 8 Jul
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"best location possible. so convenient and easy. not a luxury property but perfect for what we need. have stayed multiple times"
Carrie 1-night trip
Posted 1 hour ago
Quality Inn Great Barrington

Find out more about Hillsdale

Hillsdale Cottages information

Number of reviews
Accommodation
164 Cottages
Lowest Price
€483
Highest Price
€483

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.