Pine Plains Holiday Rentals, New York: Private House Rentals

A rustic barn surrounded by autumn foliage on a hillside.

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Our top choices for Pine Plains hotels

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Hotel

Breakfast included

Bed & breakfast

Motel

A breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.

A room with two yellow armchairs, a small table with a lamp, a framed painting on the wall, and a window with curtains.

A staircase with a wooden handrail and a wall with three framed paintings of forest scenes.

A cozy living room with a dark blue sofa, patterned armchair, and a wooden fireplace.

1. Inn at Pine Plains

Pine Plains

Katherine

Rp4.906.000

Rp5.549.914 total

includes taxes & fees

23 Aug - 24 Aug

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

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.

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

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

2. Residence Inn by Marriott Kingston

Kingston

Ali

Rp2.408.400

Rp2.697.408 total

includes taxes & fees

23 Aug - 24 Aug

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

A modern hotel room with a grey sofa, an orange armchair, a small wooden table, and a large window with sheer curtains.

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

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

3. Courtyard by Marriott Kingston

Kingston

Thuy

Rp2.107.796

Rp2.360.732 total

includes taxes & fees

23 Aug - 24 Aug

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

A modern living room with a sofa, armchair, and coffee table. There is a bed with a headboard and pillows, a lamp, and a shelf with items.

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

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

4. the Alander

Copake

Jerry

Rp3.032.800

Rp3.396.736 total

includes taxes & fees

31 Aug - 1 Sept

A swimming pool with a glass ceiling, indoor seating, and a brick wall.

A restaurant with booths, tables, and a bar area.

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

A bar area with a long counter, multiple bar stools, and a television mounted above the bar.

5. Kingston Regency Inn

Kingston

kyle

Rp2.836.560

Rp3.176.949 total

includes taxes & fees

23 Aug - 24 Aug

A wooden deck with a swing chair and a bench overlooking a lake.

A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.

A modern bar area with a counter, bar stools, and a variety of bottles.

A modern hotel room with a bed, sofa, leather chair, and a small table.

6. Interlaken Inn & Resort

Lakeville

Stacie

Rp3.997.944

Rp4.597.635 total

includes taxes & fees

20 Sept - 21 Sept

A historic white building with a porch, American flags, and a sign for Beekman Arms Inn.

A covered outdoor dining area with tables set for a meal, surrounded by columns and large windows.

A wooden interior with a barrel and a wine rack.

A covered outdoor dining area with tables set for two, featuring white tablecloths and black metal chairs.

7. Beekman Arms and Delamater Inn

Rhinebeck Village

Marisa

Rp3.207.122

Rp3.628.057 total

includes taxes & fees

31 Aug - 1 Sept

A buffet with labeled food stations including omelets and cheese.

A hotel lobby with seating areas, a reception desk, and a display of local attractions.

A hotel with a modern facade, a covered entrance, and a landscaped area with potted plants.

8. Holiday Inn Express & Suites Kingston-Ulster by IHG

Lake Katrine

Mark

Rp2.247.840

Rp2.517.582 total

includes taxes & fees

20 Sept - 21 Sept

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

A house with a stone patio and wooden stools.

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

9. Little Cat Lodge

Copake Falls

Jolie

Rp3.933.720

Rp4.405.767 total

includes taxes & fees

23 Aug - 24 Aug

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

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".

An indoor swimming pool with clear water, a 5 feet deep sign, and a tiled floor.

10. Hampton Inn Kingston

Kingston

stephen

Rp2.355.237

Rp2.637.864 total

includes taxes & fees

20 Sept - 21 Sept

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

A hotel room with a bathroom, a bed, a desk, and a nightstand.

A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

11. Quality Inn Great Barrington

Great Barrington

Lisa

Rp1.652.876

Rp1.846.262 total

includes taxes & fees

14 Sept - 15 Sept

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

A dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

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

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.

12. The White Hart

Salisbury

William

Rp6.125.364

Rp7.044.124 total

includes taxes & fees

23 Aug - 24 Aug

A row of metal chairs and a wooden barrel on a concrete floor against a wooden wall.

A hotel room with two beds, a desk with a lamp, a chair, a coffee machine, and a window with curtains.

A hotel room with two beds, a nightstand with a lamp, a chair, and a window with curtains.

A hotel room with two beds, wooden paneling, a nightstand with a lamp, and a framed picture on the wall.

13. Rhinebeck Village Inn

Rhinebeck Village

Rachel

Rp2.230.000

Rp2.522.688 total

includes taxes & fees

23 Aug - 24 Aug

A building entrance with a covered porch, stone pillars, and a mailbox.

A hotel lobby with a check-in counter, two armchairs, a small table, and a mirror.

A hotel room with two beds, a nightstand, a lamp, an air conditioning unit, and a window with curtains.

A hotel dining area with wooden tables and chairs, a kitchen counter, a refrigerator, and a television on the wall.

14. Quality Inn Hyde Park Poughkeepsie North

Hyde Park

Joshua

Rp1.525.058

Rp1.725.221 total

includes taxes & fees

13 Sept - 14 Sept

An outdoor patio with a fire pit, seating, and umbrellas.

A two-story building with a balcony, outdoor seating area with umbrellas, and potted plants.

A bedroom with a large bed, a dresser, a chair, and a table. There are three windows with blinds, and a lamp is on a nightstand.

A bedroom with a bed, a sofa, a wooden bench, a window, and a door.

15. The Millerton Inn

Millerton

Bernadette

Rp4.479.624

Rp5.067.630 total

includes taxes & fees

22 Aug - 23 Aug

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

16. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Lisa

Rp3.472.556

Rp3.878.845 total

includes taxes & fees

25 Aug - 26 Aug

A hotel room with two beds, a nightstand, a lamp, and two framed pictures on the wall.

A bathroom with a walk-in shower, grab bars, and a white tiled wall.

A hotel lobby with a reception desk, two armchairs, a small table, and a lamp.

A compact hotel room with a wooden dresser, a television, a microwave, a small refrigerator, a trash bin, and a chair.

17. Super 8 by Wyndham Kingston

Kingston

Simon

Rp1.503.087

Rp1.683.459 total

includes taxes & fees

13 Sept - 14 Sept

A room with a view of a lake, a balcony with a table and chairs, and a sofa.

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

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

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

18. Rhinecliff Hotel

Rhinecliff

RONDA

Rp3.416.003

Rp3.864.353 total

includes taxes & fees

3 Sept - 4 Sept

An indoor swimming pool with a brick border, surrounded by lounge chairs and tables.

A hotel hallway with a patterned carpet, doors on both sides, and wall-mounted lights.

A restaurant with a bar area, wooden booths, and a coffee machine.

A hotel room with two beds, a TV, a dresser, and a door leading to another room.

19. Howard Johnson by Wyndham Saugerties

Saugerties

grant

Rp2.057.702

Rp2.304.626 total

includes taxes & fees

13 Sept - 14 Sept

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Stay near popular Pine Plains attractions

Stissing Lake Park

Stissing Lake Park offers a serene lakeside escape with clear waters perfect for swimming and fishing. Families gather at picnic areas surrounded by natural beauty, creating a peaceful retreat from everyday life.

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The Stissing Center

This restored historic venue hosts diverse performances from music to theatre in Pine Plains, New York. Immerse yourself in intimate cultural experiences where historic charm meets modern artistic expression.

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Thompson Pond

8.0/10 (1 review)

This 15,000-year-old glacial kettle pond offers a peaceful 2.7-mile trail through diverse ecosystems. Bring binoculars to spot some of the 160 bird species that inhabit this National Natural Landmark.

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Gallatin Town Hall

Gallatin Town Hall serves as the administrative heart of the community, hosting public meetings and town services. Monthly board meetings are held on the third Tuesday at 6:30 PM.

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Pine Plains Library

This welcoming community library offers diverse programmes and a rich collection. Enjoy comfortable reading areas and free Wi-Fi while exploring local history resources with help from knowledgeable staff.

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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.

See all hotels in Pine Plains

Top Pine Plains Hotel Reviews

Quality Inn Great Barrington

8/10 Good

"We only stayed a night but the rooms were clean enough and the staff was extremely kind. Would stay here again."

Hampton Inn Kingston

10/10 Excellent

"Great stay. Great breakfast!"

Courtyard by Marriott Kingston

10/10 Excellent

"Convenient"

Residence Inn by Marriott Kingston

10/10 Excellent

"Room was spacious and this location is very close to everything you could possibly need. Pet friendly and great patio area! We will be back!"

St. Charles Hotel

8/10 Good

"The place was clean and reasonably priced and perfectly located for a jaunt around Hudson. However one of the lamps in my room wasn’t functional and there was no hair dryer. Small things but noticeable. The details are small but noticeable. But I would stay there again of traveling to Hudson"

AutoCamp Catskills

10/10 Excellent

"Wonderful experience!"

Little Cat Lodge

10/10 Excellent

"Was much nicer than the photos and description, it usually goes the other way. The room was spacious, pool was great, lots of activities on site, excellent view and location. Looking forward to coming back!"

Howard Johnson by Wyndham Saugerties

8/10 Good

"The staff was friendly and professional. The free parking was a plus. Access to key area roads was great. My room was clean and the bed was comfortable."

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

8/10 Good

"Much better than expected for location and ratings shown when I booked."

More cheap stays in Pine Plains

Super 8 by Wyndham Kingston

487 Washington Ave Kingston NY

Rp1.503.087

Rp1.683.459 total

13 Sept - 14 Sept

includes taxes & fees

6.2/10 (1,022 reviews)