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
10 July - 12 July
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Hillsdale cottages

Terrace/patio

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 AU$440
includes taxes & fees
29 June - 30 June
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 AU$512
includes taxes & fees
28 June - 29 June
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 AU$801
includes taxes & fees
29 June - 30 June
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 AU$509
includes taxes & fees
29 June - 30 June
Pet Friendly • Fenced Yard • Hot Tub • Romantic
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 AU$3,568
includes taxes & fees
21 July - 22 July
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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"Best hotel breakfast I have had in a long time. The breakfast attendant kept items well stocked. She made sure that vacated tables were cleaned and ready for the next guests to enjoy their meal. The room was kept very clean. I really enjoyed the fresh pancakes that were made to order by a pancake machine! Also, the pool and hot tub were great. The area was kept clean and towels were well stocked. Our room was also very spacious and immaculate."
Helen 1-night trip
Posted 2 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Hillsdale

Hillsdale Cottages information

Number of reviews
17
Accommodation
158 Cottages
Lowest Price
AU$440
Highest Price
AU$3,568

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.