Pine Plains Holiday Rentals, New York: Private House Rentals

A rustic barn surrounded by autumn foliage on a hillside.

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Go beyond your typical stay in Pine Plains

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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

฿9,221

฿10,431 total

includes taxes & fees

22 Oct - 23 Oct

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

2. Beekman Arms and Delamater Inn

Rhinebeck Village

Victoria and Scott

฿5,115

฿5,787 total

includes taxes & fees

9 Nov - 10 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 stone building with multiple windows and a door, situated on a street corner.

A modern building with multiple windows and a landscaped area with decorative pumpkins and a tree.

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

Lake Katrine

Timothy

฿4,359

฿4,882 total

includes taxes & fees

8 Nov - 9 Nov

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

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

4. the Alander

Copake

Joseph

฿5,700

฿6,384 total

includes taxes & fees

14 Oct - 15 Oct

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

An indoor swimming pool with lounge chairs and a view of the outside.

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.

5. Residence Inn by Marriott Kingston

Kingston

Lamisa

฿4,507

฿5,048 total

includes taxes & fees

8 Nov - 9 Nov

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

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

6. Courtyard by Marriott Kingston

Kingston

Ana

฿4,247

฿4,756 total

includes taxes & fees

25 Oct - 26 Oct

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

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 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.

7. The Millerton Inn

Millerton

Chelsy

฿8,419

฿9,524 total

includes taxes & fees

20 Oct - 21 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 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 dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

8. The White Hart

Salisbury

William

฿30,278

฿34,819 total

includes taxes & fees

24 Oct - 25 Oct

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

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

A swimming pool with a person in the water, surrounded by outdoor furniture and a building with a balcony.

A staircase with ornate black railings and a large chandelier.

9. Mirbeau Inn & Spa

Rhinebeck Village

Maria

฿16,446

฿18,605 total

includes taxes & fees

9 Nov - 10 Nov

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

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

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

A tented area with lush greenery and a dining setup.

10. Interlaken Inn & Resort

Lakeville

Stacie

฿8,118

฿9,335 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

11. Hampton Inn Kingston

Kingston

Jennifer

฿4,427

฿4,958 total

includes taxes & fees

12 Nov - 13 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 living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

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

12. The Harlow House

Rhinebeck

Lauren

฿6,751

฿7,637 total

includes taxes & fees

2 Nov - 3 Nov

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

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

A modern lobby with a reception desk, seating area, and a dining section.

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

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

Saugerties

Linda

฿4,271

฿4,784 total

includes taxes & fees

11 Nov - 12 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 traditional living room with a fireplace, floral patterned sofa, and a patterned rug.

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

A two-story house with a porch, a front door, and a mailbox.

14. Changing Times Boutique Country Lodging

Craryville

Thomas

฿6,706

฿7,511 total

includes taxes & fees

26 Oct - 27 Oct

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

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

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

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

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

Great Barrington

Kelly

฿4,831

฿5,397 total

includes taxes & fees

2 Nov - 3 Nov

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 historic hotel with a prominent tower and a brick facade.

16. Diamond Mills Resort

Saugerties

฿8,939

฿10,852 total

includes taxes & fees

14 Oct - 15 Oct

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

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

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

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

17. Quality Inn Hyde Park Poughkeepsie North

Hyde Park

Jon

฿2,423

฿2,741 total

includes taxes & fees

11 Nov - 12 Nov

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

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

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.

18. Jenny's Country Manor

Red Hook

amanda

฿4,694

฿5,310 total

includes taxes & fees

14 Oct - 15 Oct

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

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

19. Millbrook Country House Bed & Breakfast

Millbrook

kenneth

฿8,047

฿9,103 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

20. Rhinebeck Village Inn

Rhinebeck Village

Rachel

฿3,990

฿4,514 total

includes taxes & fees

26 Oct - 27 Oct

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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.

See all hotels in Pine Plains

Top Pine Plains Hotel Reviews

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."

Beekman Arms and Delamater Inn

10/10 Excellent

"Amazing property!"

Quality Inn Hyde Park Poughkeepsie North

8/10 Good

"Great location close to FDR, CIA and other Hyde Park sights"

Kingston Regency Inn

8/10 Good

"Good property for one night stay"

AutoCamp Catskills

8/10 Good

"Our stay was great , we really enjoyed the clubhouse the boardgames, a small hike on the property and the airstream was nicely equipped with outside grill, smart tv, and very nice outdoor space. Cleaning wise it was okay, we found hair in the shower drain, futon cover felt unwashed and I wish they had coffee in the clubhouse throughout the day. Would definitely recommend it!"

Mirbeau Inn & Spa

10/10 Excellent

"We had an exceptional stay here! The room was huge, clean, and the amenities top notch! Staff were friendly, engaging, and they could not have been more welcoming! Our spa experiences were more than wonderful, and the spa itself is one to experience for sure! An evening at the bar for dinner was heightened by exceptional service provided by Bella! We undoubtedly look forward to returning soon!"

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."

St. Charles Hotel

8/10 Good

"The St. Charles hotel is a good place to stay if you are looking for a great location to stay. It's within walking distance of restaurants and close to places to visit. However the WiFi network does kick out a lot."

Interlaken Inn & Resort

10/10 Excellent

"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."

More cheap stays in Pine Plains

Quality Inn Hyde Park Poughkeepsie North

4142 Albany Post Rd Hyde Park NY

฿2,423

฿2,741 total

11 Nov - 12 Nov

includes taxes & fees

8/10 Very good! (1,006 reviews)