Pine Plains Vacation Rentals

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Check prices for these dates

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

Browse Select Pine Plains Vacation Homes

The Farm at Hyde Park
Set amidst lush greenery and mature trees, this charming building features a steeply pitched roof and a brick facade.

The Farm at Hyde Park

9.8 out of 10, Exceptional, (74)
"We were visiting the Culinary Institute highly recommend it."
The Farm at Hyde Park
Spacious Home nestled along the Blackberry River in Northwest CT
Enjoy cooking and dining in this well-equipped kitchen with a central island, appliances, and a dining area that opens to a deck with a grill.

Spacious Home nestled along the Blackberry River in Northwest CT

10.0 out of 10, Exceptional, (86)
"The team stayed here for a curling tournament. Great location for that and perfect for 4 non-couple guests"
Spacious Home nestled along the Blackberry River in Northwest CT
Esopus Creek modern Tiny house Retreat!
Enjoy a romantic dinner for two on this deck with a beautiful floral arrangement and a bottle of wine.

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (45)
"4 of us stayed for a fishing trip and had a blast. Nice place at a reasonable price. Would stay again. "
The price is CA $204
CA $326 total
includes taxes & fees
Aug 17 - Aug 18
Esopus Creek modern Tiny house Retreat!
Charming cottage with lake access, wood burning fire place, and WiFi
Relax in this inviting living room with a sofa, dresser, and small table.

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
9.0 out of 10, Wonderful, (7)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi
Charming Catskill getaway walking distance to Main St. Pet-friendly!
Enjoy cooking in this well-lit kitchen with a central island and modern appliances.

Charming Catskill getaway walking distance to Main St. Pet-friendly!

10.0 out of 10, Exceptional, (3)
"We had a great stay here! The check in process was super easy and Jiyon was very communicative. The house was super comfortable and conveniently located for a weekend of hiking. Would definitely stay here again!"
Charming Catskill getaway walking distance to Main St. Pet-friendly!
STUNNING VACATION AND SKI HOME - Hudson Valley, Woodstock, Hunter
Enjoy cooking in this well-lit kitchen with a central island and stainless steel appliances.

STUNNING VACATION AND SKI HOME - Hudson Valley, Woodstock, Hunter

10.0 out of 10, Exceptional, (48)
"We loved our time out here and hope to be back soon!"
STUNNING VACATION AND SKI HOME - Hudson Valley, Woodstock, Hunter
Secluded family retreat within minutes of Woodstock village
Relax on the deck with a sofa, armchairs, and ottomans, taking in the view of the wooded area.

Secluded family retreat within minutes of Woodstock village

10.0 out of 10, Exceptional, (41)
"My wife and I came for just the weekend and enjoyed the house as always! Comfortable, clean, spacious, and convenient to everything yet quiet as can be. "
Secluded family retreat within minutes of Woodstock village
Stylish Cozy Home with Gorgeous Views!
Enjoy cooking in this well-equipped kitchen with a central island and modern appliances.

Stylish Cozy Home with Gorgeous Views!

10.0 out of 10, Exceptional, (25)
"Second time staying here; check in and out is super easy. Place is beautiful and comfortable. Perfect place to relax."
Stylish Cozy Home with Gorgeous Views!
Spectacular views and close to Great Barrington.
Relax in this inviting living area with a high ceiling, brick fireplace, and expansive windows offering views of the surrounding landscape.

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay in Great Barrington for the long holiday weekend. The house is very comfortable, super clean, and the property is lovely. We were able to cool off in the pool and enjoy time with family. 10/10!"
Spectacular views and close to Great Barrington.
Taconic Hideaway – Swimming, BBQ Pit, Hiking
Relax on the deck surrounded by trees, with Adirondack chairs and a small table for a peaceful retreat.

Taconic Hideaway – Swimming, BBQ Pit, Hiking

2.0 star property
10.0 out of 10, Exceptional, (6)
"Great stay. The host was great with communicating directions and details for the home and even shared local recommendations. We appreciated their quick response to our questions, too. "
Taconic Hideaway – Swimming, BBQ Pit, Hiking
Falls Reach In The Heart of Copake
Property grounds

Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake
Super Comfortable Water-view Home in Saugerties
Relax in a spacious living area with a pool table, dining space, and cozy seating area.

Super Comfortable Water-view Home in Saugerties

9.6 out of 10, Exceptional, (4)
"A very clean, spacious, and friendly environment with all the amenities you need. "
The price is CA $345
CA $994 total
includes taxes & fees
Sep 9 - Sep 10
Super Comfortable Water-view Home in Saugerties
Stylish Pine Plains Home Near Parks & Hiking!
Enjoy cooking in this fully equipped kitchen with a range, oven, microwave, and sink.

Stylish Pine Plains Home Near Parks & Hiking!

9.8 out of 10, Exceptional, (15)
"Place looked great in pictures and turned out to be even better! Will definitely stay there again."
Stylish Pine Plains Home Near Parks & Hiking!
Woodland A-Frame
Spacious living area with a high ceiling, stone accent wall, and kitchen island.

Woodland A-Frame

10.0 out of 10, Exceptional, (1)
"Nice, clean place out in the woods. Enjoyed our stay and had no issues. Host responded quickly and check-in/out was refreshingly simple. Our kid enjoyed the supply of children’s books. "
Woodland A-Frame
Poolside Luxe at Long Pond
Exterior

Poolside Luxe at Long Pond

Poolside Luxe at Long Pond
Hamptons on the Hudson in South Saugerties
Relax in a cozy outdoor space with a fireplace, wicker furniture, and a scenic view.

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (24)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties
The Chicken Coop
Relax on the covered porch with outdoor seating and grill, surrounded by a serene backyard with a brick patio and well-maintained lawn.

The Chicken Coop

9.2 out of 10, Wonderful, (7)
"Very cool place everything u need is just a short drive away "
The Chicken Coop
Brand New House w gated backyard that is located right at the Saugerties Village
Relax in this inviting living area with a high ceiling, leather sofa, and patterned rug.

Brand New House w gated backyard that is located right at the Saugerties Village

10.0 out of 10, Exceptional, (35)
"Newly remodeled and in a nice quiet neighborhood next to a store. Walking distance to downtown shops and restaurants."
The price is CA $242
CA $574 total
includes taxes & fees
Aug 11 - Aug 12
Brand New House w gated backyard that is located right at the Saugerties Village
Peaceful Catskills Creek House
Relax by the serene lake with a dock offering a bench and table for a peaceful retreat.

Peaceful Catskills Creek House

10.0 out of 10, Exceptional, (4)
"If we decide to stay in the area again this will be the first place I’ll check for availability. So cute and comfortable! "
Peaceful Catskills Creek House
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel range hood, and large window offering a view of the outdoors.

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
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

Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

10/10 Excellent
"It was very conveniently located, walkable to the downtown historic areas of town, shopping and restaurants "
Grazyna 1-night trip
Posted 1 day ago
Best Western Plus Kingston Hotel And Conference Center