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
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

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 CA $197
CA $462 total
includes taxes & fees
Jun 29 - Jun 30
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Interior

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, (11 reviews)
"Very clean, comfortable, good location, great communication with host. "
United States
Lisa B.
The price is CA $179
CA $335 total
includes taxes & fees
Jul 28 - Jul 29
Charming loft cottage in tranquil Germantown with WiFi, AC
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 CA $256
CA $509 total
includes taxes & fees
Jun 30 - Jul 1
Charming Cottage in the Heart of Catskill & Pet Friendly
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 CA $277
CA $503 total
includes taxes & fees
Jun 29 - Jun 30
Pet Friendly • Fenced Yard • Hot Tub • Romantic
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 CA $318
CA $787 total
includes taxes & fees
Jun 29 - Jun 30
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

Cozy 2-bedroom cottage in enchanting Catskill Mountains

Cozy 2-bedroom cottage in enchanting Catskill Mountains
Catskill
The price is CA $341
CA $727 total
includes taxes & fees
Jun 29 - Jun 30
Cozy 2-bedroom cottage in enchanting Catskill Mountains
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 CA $1,970
CA $3,551 total
includes taxes & fees
Jul 7 - Jul 8
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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"great bedding including a cotton blanket and full choices at breakfast with helpful staff"
Patricia 1-night trip
Posted 2 hours ago
Hampton Inn & Suites Berkshires-Lenox

Find out more about Hillsdale

Hillsdale Cottages information

Number of reviews
17
Accommodation
164 Cottages
Lowest Price
CA $462
Highest Price
CA $3,551

Frequently asked questions

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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.

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