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Compare 99 Cottages in Pine Plains with updated reviews, rates, and availability.

Charming Artist's Retreat
10.0 out of 10, Exceptional, (124)
"We had a lovely time relaxing at Maureen’e cottage for the weekend. Sitting in the garden, taking in the mountain view, and listening to the surrounding wildlife was the perfect respite from hectic city life. As artists, we felt right at home among the artwork and vintage treasures around the house. We enjoyed a hearty breakfast at the Village Diner, and loved exploring the Saugerties Lighthouse Trail - only ten minutes away! Thank you Maureen for a wonderful stay. - Dave and Alie"
Charming Artist's Retreat
Two Bedroom Cottage Close To Town
9.6 out of 10, Exceptional, (17)
"What a wonderful time we had in this beautiful cottage! The property is so idyllic and perfect for a country getaway. We couldn’t ask for more in this home & needed for nothing. The beds were comfortable and the decor was just beautiful! The property owners were so friendly and very presponsive to any questions we had. We were staying in the area because it is close to Lime Rock Park, where my son was racing. We will definitely be back to stay in this wonderful cottage! Thank you for opening...
Two Bedroom Cottage Close To Town
Loblolly Cottage - Enchanting Retreat set among towering pines.
10.0 out of 10, Exceptional, (34)
"Finally, we can rave about a home rental!! Loblolly is a quaint cabin with all of the amenities you could wish for. We cancelled dinner reservations twice because we just wanted to bring in food and enjoy the stay. Relaxing on the hammock with the firepit and outdoor kitchen was superb! Very clean, cozy and private. The homeowner lives next door but the backyard is secluded so we didn’t see him other than check-in. He checked in to be sure we had everything we needed. Otto’s Market is right up...
Loblolly Cottage - Enchanting Retreat set among towering pines.
Charming Cottage in Private Lake Community (Pet-Friendly!)
9.8 out of 10, Exceptional, (20)
"Cute cottage in upstate New York. Clean and stocked with the basics made it a great choice for our quick trip. Easy to find. Lovely yard with fire pit and grill. We did not have any questions or concerns but the hosts sent clear check in/out info. Highly recommend! "
Charming Cottage in Private Lake Community (Pet-Friendly!)
Country Cottage with beautiful views and easy access to Catskills activities.
10.0 out of 10, Exceptional, (5)
"My daughter and I stayed in this adorable little cottage while she was showing at Hits. Great location and only 6 minutes from the show grounds!"
The price is SAR 413
SAR 658 total
includes taxes & fees
11 Oct - 12 Oct
Country Cottage with beautiful views and easy access to Catskills activities.
Charming Cottage in the Heart of Catskill & Pet Friendly
10.0 out of 10, Exceptional, (10)
"We loved everything about this stylish and super clean cottage! The decor is lovely, it is well stocked with everything you need, and is in a quiet neighborhood, perfect for dog walking. We walked each morning up the hill to the convent and enjoyed looking at the older homes and gardens. You could walk into town from this place but we drove and parked along the street. There is a waterfront park nearby too. The hosts were wonderful and provided such clear instructions. The house looks completely...
Charming Cottage in the Heart of Catskill & Pet Friendly
THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need
9.6 out of 10, Exceptional, (4)
"We really enjoyed our stay and will definitely come back. Highly recommended!"
THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need
Idillic summer getaway in Litchfield Hills, CT.
10.0 out of 10, Exceptional, (12)
"The property was lovely and the property manager was very friendly and accommodating. The space was ample, beds were very comfortable, and the a/c kept us cool in the middle of a heat wave. Only issue was that the house had a very musty smell to it. Also, the coffee pot was filled with old coffee-apparently they forgot to clean it prior to our arrival. Otherwise a great stay!"
Idillic summer getaway in Litchfield Hills, CT.
Rose Cottage
10.0 out of 10, Exceptional, (2)
"It's so peaceful there. It was lovely."
Rose Cottage
Catskill Cottage, Walk to Downtown & River Views
10.0 out of 10, Exceptional, (5)
"We rented the cottage "
Catskill Cottage, Walk to Downtown & River Views
Experience Peace in this Beautiful country cottage nestled beneath the mountains
10.0 out of 10, Exceptional, (2)
"I have nothing but wonderful things to say about the property, my stay and Bridget. Inside anything you might need is right there for you. The beds are very comfy and the energy is warm and inviting. The outside is so well thought out! The firepit is perfect there is lots of room for games and fun! Plenty of wood and privacy makes for lots of outdoor fun! The deck was a favorite spot for me, so comfy and catching the morning sun on the couch is delightful! I cannot recommend this little gem...
The price is SAR 559
SAR 1,328 total
includes taxes & fees
23 Sep - 24 Sep
Experience Peace in this Beautiful country cottage nestled beneath the mountains
Reset and Relax in Luxury Cottage
10.0 out of 10, Exceptional, (26)
"We enjoyed staying at the cottage and exploring various parts of Hudson valley. "
Reset and Relax in Luxury Cottage
Charming Cottage with Expansive Hudson River Views
10.0 out of 10, Exceptional, (10)
"This was a wonderful property with a beautiful view of the Hudson Valley. The host was very accommodating. I highly recommend it. "
Charming Cottage with Expansive Hudson River Views
Fun Getaway Lakehouse in the Hudson Valley
10.0 out of 10, Exceptional, (11)
"Beautiful house with amazing views. Very clean, all brand new. Great location. We would rent it again. Had an amazing Labor Day weekend. Thank you!"
Fun Getaway Lakehouse in the Hudson Valley
The Schoolhouse, Rhinebeck Perfection
10.0 out of 10, Exceptional, (4)
"Great location to explore Rhinebeck, Red Hook, Tivoli, Kingston and the surrounding area. We hiked everyday on well-marked trails nearby, visited breweries and wineries, and had great meals in Rhinebeck. The house was perfect— separate “wings” with bedrooms and bathrooms and many places to sit and chat or read a book. The kitchen has everything you need for a short stay with condiments/teas/coffees to make things easy. Anna was super welcoming and responsive in our communications. Would...
The price is SAR 867
SAR 2,065 total
includes taxes & fees
23 Oct - 24 Oct
The Schoolhouse, Rhinebeck Perfection
Lakefront cottage with Year round Hot Tub private beach and dock
9.6 out of 10, Exceptional, (75)
"The property was exactly as described, but the pictures do not accurately show just how homey it is. The house was immaculate and had everything we could possibly need. We love the craftsman/ farmhouse style and the furnishings. The screened porch had a table and ample seating with a view overlooking the lake and the sunrise The lake was the perfect size and we took advantage of the kayaks. Our absolutely favorite part was the hot tub!"
Lakefront cottage with Year round Hot Tub private beach and dock
Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!
9.8 out of 10, Exceptional, (6)
"Our family of four stayed here for the weekend after picking up our daughter from Hawthorne Valley Farm Camp, and this property was perfect for us! The home was immaculate and cool when we arrived. Rudy communicated a few days ahead of time about an issue with the fridge and provided coolers and ice for us to use. We loved eating dinner out on the porch and playing board games down in the media room. The beds were clean and comfortable without being too soft. It made a huge difference that our...
Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (5)
"Beautifully kept, quaint little space - perfect for a relaxing getaway with a small family/friend group or two couples. Very private even though it was in back of the owners' property. The space was thoughtfully arranged and had one of the most in-depth guides to the property and surrounding areas we've ever seen! Nick and Tiffany were great hosts - I would be surprised if they didn't work in hospitality. I would go back."
The price is SAR 938
SAR 1,765 total
includes taxes & fees
14 Oct - 15 Oct
The Blue Elm - A Historic Berkshire Cottage
LAKE FRONT COTTAGE - YEAR ROUND HOT TUB
9.4 out of 10, Exceptional, (40)
"came here with my partner to celebrate my birthday. it was the perfect place to relax & wind down from living in the city. i would love to come back during warmer months!"
LAKE FRONT COTTAGE - YEAR ROUND HOT TUB
Cozy cottage with kettle pond lake 2 minutes away. FYI - No air conditioning!
9.0 out of 10, Wonderful, (2)
"This is a lovely property in a perfect, serene location. Highly recommend!"
Cozy cottage with kettle pond lake 2 minutes away. FYI - No air conditioning!
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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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Other property types in Pine Plains

Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (83)
"The owner was fantastic! Super kind and accommodating. Very available for any help or questions. Well maintained, clean and quiet property. Would definitely stay there again! "
The price is SAR 424
SAR 457 total
includes taxes & fees
6 Oct - 7 Oct
Micosta Leisure Inn
The Farm at Hyde Park
9.8 out of 10, Exceptional, (61)
"We came up from Brooklyn to see the hot air balloons with my parents and it was just what we needed. Our Host Glen is very gracious and helpful! We loved staying at the Farm. The church and the grounds are beautiful. Glen provided us with fresh eggs, milk and honey. We were also allowed to pick tomatoes from his garden. All very delicious. "
The Farm at Hyde Park
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very Good, (41)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is SAR 469
SAR 544 total
includes taxes & fees
25 Sep - 26 Sep
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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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