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

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

A neatly made bed with white and brown pillows, two bedside lamps, and framed pictures on the wall.

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.

1. Inn at Pine Plains

Pine Plains

teresina

7.115.075 ₫

8.048.930 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A large, multi-story hotel with a symmetrical facade, multiple balconies with flower boxes, and a central entrance with a fountain.

A staircase with ornate black railings and a large chandelier.

A building with a central entrance, multiple windows, and outdoor seating.

A spa area with a large rock centerpiece, multiple seating areas, and a skylight ceiling.

2. Mirbeau Inn & Spa

Rhinebeck Village

Maria

12.393.167 ₫

14.019.803 ₫ total

includes taxes & fees

16 Nov - 17 Nov

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

A bar area with a variety of liquor bottles, a menu board, and a rustic wooden backdrop.

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

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

3. Beekman Arms and Delamater Inn

Rhinebeck Village

Katherine

3.935.283 ₫

4.451.789 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

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

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

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

4. the Alander

Copake

Luis

4.269.045 ₫

4.781.330 ₫ total

includes taxes & fees

13 Nov - 14 Nov

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.

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.

5. Courtyard by Marriott Kingston

Kingston

Ana

3.276.815 ₫

3.670.034 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

An outdoor patio with a round table and orange chairs, a black metal fence, and string lights.

A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.

A stone building with multiple windows and a door, situated on a street corner.

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

Lake Katrine

Timothy

3.156.506 ₫

3.535.286 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

A tented area with lush greenery and a dining setup.

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.

7. Interlaken Inn & Resort

Lakeville

Stacie

6.962.424 ₫

8.006.788 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A bathroom with a white toilet, a wooden vanity with a sink, and a mirror above the vanity. There are two wall-mounted light fixtures and a towel rack above the toilet.

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 long dining table set with multiple wine glasses, water glasses, and folded white napkins.

8. The Millerton Inn

Millerton

Chelsy

6.496.710 ₫

7.349.402 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A balcony with a table featuring a bottle, glasses, and binoculars, overlooking a river, greenery, and a house.

A dining area with a brick fireplace, wooden beams, and a chandelier.

A bar with a patterned floor, bar stools, and a bar counter with taps.

9. Diamond Mills Resort

Saugerties

luping

6.876.526 ₫

8.348.441 ₫ total

includes taxes & fees

19 Oct - 20 Oct

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

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

10. The White Hart

Salisbury

William

7.986.995 ₫

9.185.174 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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.

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

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

11. Residence Inn by Marriott Kingston

Kingston

Lamisa

3.699.839 ₫

4.143.821 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

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.

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

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

12. Hampton Inn Kingston

Kingston

Jennifer

3.161.163 ₫

3.540.501 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A modern bedroom with a large bed, a red sofa, a fireplace, and a television.

A wooden deck with wicker chairs and a small table, overlooking a forested area.

A room with a long wooden table, multiple chairs, a sofa, and large windows offering a forest view.

A window with a view of a forested area, a small potted plant, and a black kettle on the windowsill.

13. The Harlow House

Rhinebeck

George

5.134.497 ₫

5.808.399 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A vintage black car parked on a road with a white fence and trees in the background.

A two-story house with a front porch, a garage with a red car, and a driveway with a black car.

A dining area with wooden chairs and tables, a central wooden display cabinet with glass doors, and a green-lit wall lamp.

A living room with a fireplace, a sofa, a chair, and a coffee table.

14. Jenny's Country Manor

Red Hook

amanda

3.622.220 ₫

4.097.766 ₫ total

includes taxes & fees

21 Oct - 22 Oct

A wooden cabin with a circular window overlooking a lake and grassy area.

A restaurant with round tables, potted plants, and a glass of wine on a table.

A row of modern cabins with large windows, surrounded by a grassy field and trees.

A cozy room with a bed, two white chairs, a table with breakfast items, and a view of a snowy landscape through a large window.

15. Hutton Brickyards Riverfront Hotel + Venue

Kingston

Victoria

7.102.138 ₫

8.730.583 ₫ total

includes taxes & fees

28 Oct - 29 Oct

A Holiday Inn Express hotel with a covered entrance, multiple floors, and a brick facade.

A modern breakfast area with a coffee machine, cereal, and bakery options.

A hotel lobby with a reception desk, seating area, and a corridor leading to other rooms.

A Holiday Inn Express & Suites sign with a clear view of the hotel building in the background.

16. Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Saugerties

Linda

3.182.379 ₫

3.564.264 ₫ total

includes taxes & fees

15 Nov - 16 Nov

A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

A room with a white door, a window, and a wall with various framed pictures.

A traditional living room with a fireplace, floral patterned sofa, and a patterned rug.

A fire pit with two Adirondack chairs, a table with drinks, and a house in the background.

17. Changing Times Boutique Country Lodging

Craryville

Thomas

5.174.600 ₫

5.795.552 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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

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

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.

18. Quality Inn Great Barrington

Downtown Great Barrington

Scott Patterson

1.957.292 ₫

2.186.295 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A garden with a variety of plants and flowers, a white picket fence, and a small table with chairs.

A garden with various plants and flowers, a white fence, and outdoor furniture.

A hallway with a table, a vase with flowers, a framed picture, and a painting on the wall.

A formal dining table set with plates, cutlery, and wine glasses, surrounded by chairs.

19. Millbrook Country House Bed & Breakfast

Millbrook

kenneth

6.209.520 ₫

7.024.520 ₫ total

includes taxes & fees

30 Oct - 31 Oct

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 gym with exercise equipment, a mirror, and a door leading to a room.

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

20. Quality Inn Hyde Park Poughkeepsie North

Hyde Park

Jon

1.869.324 ₫

2.114.673 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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Hotels recommended for families in Pine Plains

Inn at Pine Plains

Pine Plains

7.115.075 ₫

8.048.930 ₫ total

includes taxes & fees

18 Oct - 19 Oct

Changing Times Boutique Country Lodging

Craryville

5.174.600 ₫

5.795.552 ₫ total

includes taxes & fees

28 Oct - 29 Oct

Holiday Inn Express & Suites Kingston-Ulster by IHG

Lake Katrine

3.156.506 ₫

3.535.286 ₫ total

includes taxes & fees

15 Nov - 16 Nov

Courtyard by Marriott Kingston

Kingston

3.276.815 ₫

3.670.034 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

A single bed with a wooden frame, white bedding, and a patterned throw. There is a wooden floor and a small rug in front of the bed.

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

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

Rhinecliff Hotel

Rhinecliff

4.418.591 ₫

4.998.531 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

A two-story building with a covered porch and a stone chimney.

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.

Rhinebeck Village Inn

Rhinebeck Village

3.078.887 ₫

3.482.990 ₫ total

includes taxes & fees

7 Nov - 8 Nov

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Stay near popular Pine Plains attractions

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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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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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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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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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.

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Top Pine Plains Hotel Reviews

Beekman Arms and Delamater Inn

10/10 Excellent

"We loved the uniqueness of this very special inn. The history is amazing. Our room had been upgraded to include a bathroom, tv, etc., of course, but still felt timeless."

Mirbeau Inn & Spa

10/10 Excellent

"An incredible experience from the moment we checked in until we left. The hotel was beautiful with great amenities. The spa was perfect and spent an enjoyable day there with my sisters. The staff couldn’t be friendlier and more helpful. Love the location, easy access to downtown to all the shops and great restaurants. Highly recommend."

Quality Inn Great Barrington

10/10 Excellent

"good location, friendly helpful staff"

Quality Inn Hyde Park Poughkeepsie North

8/10 Good

"There is some wear and tear on the rooms, they could do with a refresh. But the room was clean. The breakfast was good - with waffles, eggs, sausage, yogurt fruit, juice and coffee. Close to nearby attractions like the FDR Library as well."

Super 8 by Wyndham Kingston

8/10 Good

"Josh was super helpful at Check-in. Very accommodating and super polite. The property was heavily used by semi-permanent guests and needed a bit of cleaning. I was there to close out a storage unit, so the accommodation was very adequate with close proximity to good eateries and downtown Kingston. My room was quiet and had everything I needed. All good."

Hotel Kinsley

8/10 Good

"Check in staff only provided information on parking and the address our room was located. It would have been extremely helpful to inform us of the free breakfast, restaurant coupon and the use of the outdoor patio as we bought breakfast out and paid for dessert at the Hotel Kinsey restaurant. The room was very clean."