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Browse Select Pine Plains Cottages

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!)

Rose Cottage

9.6 out of 10, Exceptional, (5)
"It's so peaceful there. It was lovely."
Rose Cottage

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

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

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

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.

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

9.8 out of 10, Exceptional, (140)
"Enjoyed our stay!"
Charming Artist's Retreat

Private Woodstock cottage. Don't forget your dog!

10.0 out of 10, Exceptional, (9)
"The property was Great! It was close to town, but far enough away for a little peace and quiet. The place itself was very clean, comfortable, and great for a couples weekend retreat."
Private Woodstock cottage. Don't forget your dog!

4 Mi to Dtwn Catskill: Mtn-view Home

3.0 star property
4 Mi to Dtwn Catskill: Mtn-view Home

Waterfall, Back Yard, and Fire Pit!

The price is CA $497
CA $713 total
includes taxes & fees
Aug 12 - Aug 13
Waterfall, Back Yard, and Fire Pit!

THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need

9.0 out of 10, Wonderful, (8)
"We really enjoyed our stay and will definitely come back. Highly recommended!"
THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need

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

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 $619 total
includes taxes & fees
Aug 31 - Sep 1
Hits Adjacent | Pet Friendly | Caraway Cottage

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

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

3.0 star property
West Cornwall Cabin ~ 4 Mi to Covered Bridge!

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

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

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 $245 total
includes taxes & fees
Aug 18 - Aug 19
Country Cottage with beautiful views and easy access to Catskills activities.

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (8)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is CA $275
CA $567 total
includes taxes & fees
Aug 11 - Aug 12
The Blue Elm - A Historic Berkshire Cottage
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