Search Pine Plains Cottage Rentals from CA $171

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Check prices for these dates

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

Our top choices for Pine Plains cottages

A kitchen with white cabinetry, granite countertops, and a window with blinds.

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 CA $171
CA $347 total
includes taxes & fees
Nov 16 - Nov 17
Charming loft cottage in tranquil Germantown with WiFi, AC
A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

2. 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 CA $308
CA $667 total
includes taxes & fees
Nov 15 - Nov 16
Sharon Retreat w/ Private Yard
A single-story house with a black front door, two windows on either side, and two black trash bins in front.

3. 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 CA $271
CA $500 total
includes taxes & fees
Nov 15 - Nov 16
Charming Cottage in the Heart of Catskill & Pet Friendly
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, (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 CA $184
CA $458 total
includes taxes & fees
Nov 16 - Nov 17
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, (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 CA $343
CA $694 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 2-bedroom cottage in enchanting Catskill Mountains
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 Pine Plains

Hike the trails of Stissing Mountain for panoramic views of this charming Hudson Valley town and its surrounding countryside. Spend afternoons exploring local farm stands or enjoying the peaceful waters of Stissing Lake with a picnic from Main Street businesses.

See all hotels in Pine Plains
A rustic barn surrounded by autumn foliage on a hillside.

Top reviews in Pine Plains

A hotel with a covered entrance, stone facade, and a sign indicating it is a Holiday Inn Express & Suites.
Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG
Lake Katrine

10/10 Excellent

Parfait pour une pause lors de trajet en voiture. Propre, accueillant , confortable. Personnel courtois et attenionné.
Canada
Martin
Reviewed November 5, 2026
Holiday Inn Express & Suites Kingston-Ulster by IHG

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