Villas in Pine Plains
New York
United States of America
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A rustic barn surrounded by autumn foliage on a hillside.

Search Pine Plains Villa Rentals from CA $264

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your current months are November, 2026 and December, 2026.

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Our top choices for Pine Plains villas

An outdoor patio with a fire pit, wicker furniture, and string lights.

A dining area with a round table, black chairs, a neon sign, and a brick wall.

A modern kitchen with a dining area, featuring stainless steel appliances, a brick accent wall, and a neon sign.

A modern living room with a leather sectional sofa, a coffee table, and a desk with a globe lamp.

1. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Stottville

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Enjoyed our 2 night stay, everything was clean and worked smoothly. The hot tub and couch were the favorites, also enjoyed the coffee maker very much. Would highly recommended staying here!"

Ross O.

The price is CA $264

CA $264

CA $493 total

includes taxes & fees

Nov 17 - Nov 18

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson 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.

View all properties

Learn more about Pine Plains

Hike the trails of Stissing Mountain for panoramic views of this charming Hudson Valley town and its surrounding countryside. Spend afternoons exploring local farm stands or enjoying the peaceful waters of Stissing Lake with a picnic from Main Street businesses.

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Top reviews in Pine Plains

A hotel with a covered entrance, stone facade, and a sign indicating it is a Holiday Inn Express & Suites.

A row of refrigerators with shelves stocked with beverages and condiments.

A hotel lobby with a reception desk, seating area, and a refrigerator stocked with beverages.

A buffet with various food items, including omelets and baked goods, served in metal containers.

Holiday Inn Express & Suites Kingston-Ulster by IHG

Lake Katrine

10/10 Excellent

Parfait pour une pause lors de trajet en voiture. Propre, accueillant , confortable. Personnel courtois et attenionné.

Martin

Reviewed November 5, 2026Reviewed November 5, 2026

Holiday Inn Express & Suites Kingston-Ulster by IHG

A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

A dining table set with plates of food, wine glasses, and bottles, with a chandelier above and shelves above holding glasses and bottles.

A bar area with a green counter, two pendant lights, and shelves stocked with bottles.

A dog standing at a door entrance with a wooden floor and a mat with paw prints.

the Alander

Copake

10/10 Excellent

Loved our stay, staff very attentive and helpful!!

Kelly

Reviewed May 24, 2025Reviewed May 24, 2025

the Alander

A balcony with a white table and chairs, overlooking a body of water and distant land.

A room with a flat-screen TV mounted on the wall, two brown armchairs, a woven rug, and a wooden floor.

A building with a yellow exterior, a door with a glass panel, a potted plant, and a sign indicating accessibility.

A bathroom with a freestanding bathtub, a window with blinds, and a towel rack.

Rhinecliff Hotel

Rhinecliff

10/10 Excellent

Clean room, cozy beautiful area and place

Farzad Attar

Reviewed June 27, 2026Reviewed June 27, 2026

Rhinecliff Hotel

A Hampton Inn hotel with a modern facade, multiple entry points, and a well-lit entrance.

A candy store with shelves of various treats and a sign that reads "TREATS".

A spacious living area with a sofa, armchairs, and a coffee table. There is a dining area with chairs and a table, and a stone fireplace.

A spacious living area with a fireplace, a dining table with chairs, and a television mounted on the wall.

Hampton Inn Kingston

Kingston

10/10 Excellent

Très bien, bon service et bien situé pour reprendre

carl

Reviewed July 2, 2026Reviewed July 2, 2026

Hampton Inn Kingston

A Courtyard by Marriott hotel with a modern facade, large windows, and a well-maintained entrance area.

A modern cafe with a wooden counter, bar stools, and a menu board above the counter.

An outdoor patio with a fire pit, seating, and a building in the background.

A hotel room with two beds, a desk, a chair, and a large window with curtains.

Courtyard by Marriott Kingston

Kingston

10/10 Excellent

Beautiful new rooms, staff was very friendly and helpful. Really enjoyed our stay.

Ana

Reviewed September 10, 2026Reviewed September 10, 2026

Courtyard by Marriott Kingston

A bedroom with a large bed, a chair, and a window with curtains.

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

A framed painting of a white horse on a wooden dresser, a white fireplace with a black mantle, and two green vases with white flowers on the wall.

A covered porch with a dining area, a sofa, and decorative wall art.

The White Hart

Salisbury

10/10 Excellent

They upgraded us to a 2-room suite at no extra charge!

Andy

Reviewed May 14, 2018Reviewed May 14, 2018

The White Hart

A multi-story hotel with a well-lit entrance, a flag, and a sign indicating it is a Marriott Residence Inn.

A spacious lobby with a fireplace, comfortable seating, and large windows.

An outdoor patio with a fire pit, wicker furniture, and a red building in the background.

A breakfast buffet setup with a variety of food items, including bread, cereal, and fruits, in a modern hotel dining area with striped chairs and a large window.

Residence Inn by Marriott Kingston

Kingston

10/10 Excellent

Great location, great staff

Jean

Reviewed May 26, 2026Reviewed May 26, 2026

Residence Inn by Marriott Kingston

A two-story building with a brick facade and a flat roof.

An outdoor seating area with a stone table and wicker furniture.

A modern interior with a round mirror reflecting a dining area, a large vase, and a guitar.

A modern kitchen with a built-in oven, microwave, and stainless steel range hood.

Howard Hotel

Hudson

10/10 Excellent

Loved how we felt like we were walking into our own place instead of just another hotel. The room was so nice, large, clean, bright. I’ve already recommended it to others.

Alexandra

Reviewed August 6, 2026Reviewed August 6, 2026

Howard Hotel

A two-story house with a covered porch and a small front yard.

A hallway with a bed in the background, a door with the number 4, and a small table with water bottles and a coffee maker.

A black rocking chair in front of a house with a sign that reads "The Nest" and a small potted plant beside the door.

A bedroom with a large bed, a desk with a mirror, a television on the wall, and a chandelier.

The Nest Hudson

Hudson

10/10 Excellent

Great stay! Great location!

Amanda

Reviewed January 1, 2026Reviewed January 1, 2026

The Nest Hudson

Frequently Asked Questions

Why book your villa in Pine Plains with Expedia?

We think arranging a vacation shouldn't be hard, so if you're on the lookout for villas at a competitive price, Expedia has your back. Keep costs down and pick an all-inclusive stay, or splurge on a deluxe villa to spoil your favorite people. Our search filters make it easy to secure a property in Pine Plains that checks your boxes.

How can I find cheap villas in Pine Plains?

With Expedia's user-friendly filter tool, locating cheap villas in Pine Plains is a snap. To discover accommodations that will keep some cash in your pocket, narrow down your search by amenities, budget and star rating.

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Mohonk Preserve Visitor Center
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Search Pine Plains Villa Rentals from CA $264

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Pine Plains villas

1. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Learn more about Pine Plains

Top reviews in Pine Plains

Holiday Inn Express & Suites Kingston-Ulster by IHG

10/10 Excellent

Frequently Asked Questions

Why book your villa in Pine Plains with Expedia?

How can I find cheap villas in Pine Plains?

Explore a world of travel with Expedia