Holiday houses in Pine Plains

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Popular amenities for Pine Plains holiday rentals

Stay near Pine Plains's top sights

Stissing House72 locals recommend
Stissing Mountain Fire Tower Parking Area15 locals recommend
Peck's Food Market6 locals recommend
Hammertown Barn4 locals recommend
Lia's3 locals recommend
Tower Pizza5 locals recommend

Other great holiday rentals in Pine Plains

Guest favourite
Home in Windham
5 out of 5 average rating, 22 reviews

Cozy Mountain Cabin Near Windham Slopes

MardaRating, 5 stars3 weeks ago
Impressed by the attention to detail! Communication was seamless! The host was responsive and considerate, ensuring our stay was comfortable from start to finish The host stocked the kitchen with essentials. Highly recommend to anyone looking for a cozy and clean place to stay!
Top Guest favourite
Home in Athens
5 out of 5 average rating, 38 reviews

Perfect home for a getaway from NYC

ScottRating, 5 stars1 month ago
Antonio and Yoon's place was perfect for our large group and dog. It's a very spacious home that is thoughtfully designed and in a lovely residential community. The beds and furniture were extremely comfortable, the backyard huge with a large patio and a fire pit. The six bedrooms, three full bathrooms, two living rooms, dining room, fully stocked kitchen, and finished basement gave our group of ten adults more than enough room to both gather together and enjoy time on our own. The location is near wonderful hikes and great restaurants and shops in Athens, Catskill, Hudson, and more. Antonio and Yoon were proactive, friendly, and clear in all communications. Highly recommended!
Top Guest favourite
Home in Millerton
4.96 out of 5 average rating, 185 reviews

Vacation Home In Millerton

BettyRating, 5 stars2 weeks ago
We wanted to get away from the city for some peace and quiet and Corina’s place was exactly what we were looking for. It felt very tucked away. The home was stocked with pretty much anything I think one would need. The outdoor space is huge, nice and safe for our dog to frolic. Loved the large firepit - wish we had more time to sit outside. Corina was super friendly, accommodating, and extremely quick to respond to any inquiries, so you should be in good hands if you need any help. I like to try a new airbnb whenever I can, but when we return to Millerton, we’ll be going back to Corina’s!
Guest favourite
Home in Cornwallville
4.92 out of 5 average rating, 50 reviews

Catskill/Windham Gorgeous Home

SwetaRating, 5 stars2 months ago
Stan is an amazing host and was so courteous that he cleaned up the drive way when it snowed like crazy. He was extremely warm and nice to our daughter and it was great experience. We enjoyed the house and hospitality.
Guest favourite
Home in Hensonville
5 out of 5 average rating, 10 reviews

Perfect Windham & Hunter Ski House 2 Miles to Mntn

PeterRating, 5 stars2 months ago
One of the best Airbnbs I've stayed at. The house is amazing - spacious, cozy, ad each room had their own temperature control! Plenty of communal space and the kitchen was very functional. The hosts were so responsive and nice and even offered to mail a piece of clothing we had left at the house afterwards. Definitely would come back again and highly recommended.
Top Guest favourite
Home in Great Barrington
5 out of 5 average rating, 13 reviews

Great Barrington Ranch. Sleeps 10,Hot Tub, 5 acres

JuanRating, 5 stars1 month ago
We loved this airbnb! The location was perfect very close to Catamount where we went skiing. The house had plenty of space for 9 people. The best part was the host though. Alyssa’s communication is great and she was very flexible and helpful. Would definitely stay again!
Top Guest favourite
Home in Athens
5 out of 5 average rating, 16 reviews

Lake house with arcade games

AdrienneRating, 5 stars3 months ago
Rosane and Daniel's place was great. Very clean and comfortable. It was well stocked with everything we needed.
Guest favourite
Cabin in Shandaken
4.99 out of 5 average rating, 105 reviews

A Place Called Home in The Catskill

KateRating, 5 stars1 month ago
We just finished a two month rental of John’s wonderful home. Our family of 5 used the home primarily on the weekends when we were enjoying ski season at Belleayre Mountain. I can’t say enough great things about this home. Our family felt totally at home - every aspect was perfectly maintained and the home maximized comfort. Our favorite part of the home was the great room where we would watch movies on the huge family sofa in front of a crackling fire. It was the perfect way to end a day of skiing. Our kids loved the downstairs family room with the foosball table and there were lots of games to play and keep everyone busy and entertained. And the kitchen is huge and very well stocked with all the appliances you will ever need. So it was a fantastic 2 months and we look forward to renting this property again!

Quick stats about holiday rentals in Pine Plains

  • Total rentals

    20 properties

  • Nightly prices starting at

    $169 AUD before taxes and fees

  • Total number of reviews

    1.5K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

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  4. Dutchess County
  5. Pine Plains