Search Pine Plains Cottage Rentals from CA $136

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Pine Plains Cottages

Rose Cottage
Situated in a forested area, this cabin features a simple design with a flat roof and a front porch with a railing, perfect for outdoor dining and grilling.

Rose Cottage

9.6 out of 10, Exceptional, (5)
"It's so peaceful there. It was lovely."
Rose Cottage
Summer Lake Cottage, private beach, Berkshire Hills, small village
Escape to a serene lakeside retreat surrounded by trees and a tranquil atmosphere.

Summer Lake Cottage, private beach, Berkshire Hills, small village

9.4 out of 10, Exceptional, (81)
"Amazing cabin, thank you for a beautiful stay! We came in for a wedding and this was a great location to where the wedding was held. "
Summer Lake Cottage, private beach, Berkshire Hills, small village
Charming Artist's Retreat
Exterior

Charming Artist's Retreat

9.8 out of 10, Exceptional, (140)
"Enjoyed our stay!"
Charming Artist's Retreat
Charming Cottage in Private Lake Community (Pet-Friendly!)
Fully equipped kitchen with refrigerator, microwave, oven, sink, and window.

Charming Cottage in Private Lake Community (Pet-Friendly!)

10.0 out of 10, Exceptional, (31)
"We enjoyed ourselves,relaxed,visited had a very enjoyable bisit"
Charming Cottage in Private Lake Community (Pet-Friendly!)
Charming Cottage in the Heart of Catskill & Pet Friendly
Enjoy outdoor dining at The New York Restaurant with tables and chairs set amidst lush greenery.

Charming Cottage in the Heart of Catskill & Pet Friendly

10.0 out of 10, Exceptional, (14)
"Really enjoyed my stay! Very thoughtful host. "
Charming Cottage in the Heart of Catskill & Pet Friendly
Two Bedroom Cottage Close To Town
Equipped with a refrigerator, microwave, oven, and dishwasher, this kitchen offers ample space for meal preparation.

Two Bedroom Cottage Close To Town

9.2 out of 10, Wonderful, (23)
"We enjoyed three nights at the cottage. It's beautifully decorated, comfortable, warm and welcoming - a perfect home base for nearby hikes and exploring the area. The large yard was perfect for playing soccer with our child. Renters note: we also had a fabulous meal at nearby restaurant Fern. "
Two Bedroom Cottage Close To Town
Hits Adjacent | Pet Friendly | Caraway Cottage
Relax in this stylish living room with a sofa, armchair, and dining area.

Hits Adjacent | Pet Friendly | Caraway Cottage

10.0 out of 10, Exceptional, (9)
"It was super cozy and very comfortable. It really is a lovely cottage. Perfect getaway. "
The price is CA $303
CA $628 total
includes taxes & fees
Aug 31 - Sep 1
Hits Adjacent | Pet Friendly | Caraway Cottage
Idillic summer getaway in Litchfield Hills, CT.
Surrounded by lush greenery, this house features a gabled roof and a prominent chimney.

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"Great spot close to Limerock Raceway - private, cute, and a perfect spot to stay! The owners are so nice and accommodating - I couldn’t say nicer things about this place and will be back!"
Idillic summer getaway in Litchfield Hills, CT.
Pet-friendly Cottage at Historic Millbrook Farm Estate
Traditional dresser with ornate carvings and multiple drawers, featuring a mirror above and a decorative candelabra.

Pet-friendly Cottage at Historic Millbrook Farm Estate

9.4 out of 10, Exceptional, (8)
"Stayed in this renovated farmhouse for a very snowy weekend. Nicely redone and furnished with spacious living/dining area. Could have fit 2 more adults or 2-3 kids. Hosts were lovely and introduced us to the goats. Too snowy and icy to get outdoors or explore much but local village has shops and kitchen was stocked with pantry staples and bottled water, milk/creamers for coffee so arrival day grocery run was not needed. Bonus large picture window let us enjoy the abundant snow from the warmth of...
Pet-friendly Cottage at Historic Millbrook Farm Estate
Country Cottage with beautiful views and easy access to Catskills activities.
Cozy cabin with a porch, featuring a front door, window, and chimney, surrounded by a grassy lawn and stone pathway.

Country Cottage with beautiful views and easy access to Catskills activities.

10.0 out of 10, Exceptional, (10)
"Great spot!"
The price is CA $136
CA $246 total
includes taxes & fees
Aug 5 - Aug 6
Country Cottage with beautiful views and easy access to Catskills activities.
Private Woodstock cottage. Don't forget your dog!
Relax in this stylish room with a large bed, sofa, and dining table, perfect for unwinding and enjoying your stay.

Private Woodstock cottage. Don't forget your dog!

10.0 out of 10, Exceptional, (9)
"Irene was wonderful! Will return!"
Private Woodstock cottage. Don't forget your dog!
Be in Nature at this Gorgeous Riverfront Cabin
Relax in this stylish living room with a sofa, armchair, and coffee table, offering a view of lush greenery.

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (18)
"Property was as advertised. Clean and nearby places we wanted to visit while, still being out of the way and quiet."
Be in Nature at this Gorgeous Riverfront Cabin
Waterfall, Back Yard, Fire pit, and Grill!
Exterior

Waterfall, Back Yard, Fire pit, and Grill!

The price is CA $314
CA $484 total
includes taxes & fees
Aug 10 - Aug 11
Waterfall, Back Yard, Fire pit, and Grill!
4 Mi to Dtwn Catskill: Mtn-view Home
House (4 Bedrooms) | Interior

4 Mi to Dtwn Catskill: Mtn-view Home

3.0 star property
4 Mi to Dtwn Catskill: Mtn-view Home
Reset and Relax in Luxury Cottage
Guests can enjoy a serene forest view from this deck with a sturdy railing.

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (40)
"Amazing floors, bathroom showers (wow!), and an awesome kitchen."
Reset and Relax in Luxury Cottage
Peaceful Goshen Cottage w/ Screened Porch & Views!
Kitchen features stainless steel appliances, white cabinetry, and a granite countertop.

Peaceful Goshen Cottage w/ Screened Porch & Views!

9.0 out of 10, Wonderful, (31)
"Enjoyed our stay very much. The accommodations suited our needs. Appreciated the cleanliness of the property and the ease of checking in/out."
Peaceful Goshen Cottage w/ Screened Porch & Views!
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Kitchen features a stainless steel toaster oven, sink, and double oven with a range hood.

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

3.0 star property
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
Relax in this cabin with a bed, large window offering a view of the surrounding water and greenery.

Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake

10.0 out of 10, Exceptional, (7)
"Very clean, cute house right on the lake. We enjoyed our time there. "
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
Creekside Cottage The Fitz House Red Hook NY
Cozy cabin surrounded by trees, featuring a small porch with two chairs and a table.

Creekside Cottage The Fitz House Red Hook NY

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay. Communication with host was excellent. Highly recommend the location for a couple."
Creekside Cottage The Fitz House Red Hook NY
Saugerties Cottage - relaxing home in nature, close to downtown, HITS & hikes
Surrounded by autumn leaves, a fire pit sits within a stone border, nestled among wooden structures and leafless trees.

Saugerties Cottage - relaxing home in nature, close to downtown, HITS & hikes

10.0 out of 10, Exceptional, (5)
"quiet sanctuary close to Woodstock and saugerties"
Saugerties Cottage - relaxing home in nature, close to downtown, HITS & hikes
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 Pine Plains Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Amazing service and cheerful staff !!! Thanks so much "
Shaniqua 2-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG