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 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

Mary

Rp4.923.325

Rp5.569.510 total

includes taxes & fees

27 Sept - 28 Sept

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 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.

2. the Alander

Copake

Thomas

Rp2.586.983

Rp2.897.420 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

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.

3. Residence Inn by Marriott Kingston

Kingston

Harold

Rp2.560.129

Rp2.867.344 total

includes taxes & fees

4 Oct - 5 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 two, featuring white tablecloths and black metal chairs.

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

A wooden interior with a barrel and a wine rack.

4. Beekman Arms and Delamater Inn

Rhinebeck Village

Mariya

Rp2.403.477

Rp2.718.933 total

includes taxes & fees

27 Sept - 28 Sept

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

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

5. The Millerton Inn

Millerton

Bernadette

Rp4.495.443

Rp5.085.469 total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

A tented area with lush greenery and a dining setup.

6. Interlaken Inn & Resort

Lakeville

Stacie

Rp3.566.278

Rp4.101.219 total

includes taxes & fees

26 Oct - 27 Oct

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

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

A hotel room with a sofa, ottoman, desk, chair, television, and a mirror.

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

7. Kingston Regency Inn

Kingston

Christopher

Rp2.309.487

Rp2.838.146 total

includes taxes & fees

27 Sept - 28 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 hotel room with two beds, a TV, a dresser, and a door leading to another room.

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

8. Howard Johnson by Wyndham Saugerties

Saugerties

Richard

Rp2.488.517

Rp2.787.140 total

includes taxes & fees

27 Sept - 28 Sept

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

A wooden fire pit surrounded by six Adirondack chairs in 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.

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

9. Little Cat Lodge

Copake Falls

Kees

Rp3.206.427

Rp3.591.198 total

includes taxes & fees

27 Sept - 28 Sept

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

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

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.

10. Courtyard by Marriott Kingston

Kingston

Ana

Rp2.267.415

Rp2.539.506 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

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

Lake Katrine

Bailey

Rp2.327.390

Rp2.606.675 total

includes taxes & fees

25 Oct - 26 Oct

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

12. The White Hart

Salisbury

William

Rp6.165.793

Rp7.090.662 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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.

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

Great Barrington

Bruce

Rp3.028.292

Rp3.382.603 total

includes taxes & fees

1 Oct - 2 Oct

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".

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.

14. Hampton Inn Kingston

Kingston

stephen

Rp2.515.551

Rp2.817.417 total

includes taxes & fees

26 Oct - 27 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 room with a bathroom, a bed, a desk, and a nightstand.

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

15. Quality Inn Great Barrington

Great Barrington

Kimberly

Rp1.810.888

Rp2.022.761 total

includes taxes & fees

18 Oct - 19 Oct

A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

A two-story building with a flat roof, solar panels, and a small patio area.

A bedroom with a wooden bed, two bedside tables, a window with curtains, and a radiator.

A covered porch with white railings and rocking chairs.

16. Locust Tree Bed and Breakfast LLC

East Canaan

Nicholas

Rp1.879.815

Rp2.161.787 total

includes taxes & fees

27 Sept - 28 Sept

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

A room with a fireplace, two striped armchairs, and a floral drape.

A cozy living room with floral wallpaper, a sofa, a coffee table, and two lamps.

A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.

17. Blackberry River Inn

Norfolk

Brian

Rp2.685.450

Rp3.088.267 total

includes taxes & fees

27 Sept - 28 Sept

A living room with a leather sofa, a wooden coffee table, a TV on a wooden stand, and a window with curtains.

A cozy lobby with patterned sofas, a wooden reception desk, and a mirror reflecting the interior.

A storefront with a 'DEFACE' sign, a 'NO PETS' notice, and various seasonal decorations including pumpkins and flowers.

A hotel room with two beds, a wooden dresser, a television, and a stone wall.

18. Red Ranch Motel

Catskill

Dhan

Rp2.300.894

Rp2.484.936 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

A multi-story hotel with a flat roof, large windows, and a brick facade.

19. Super 8 by Wyndham Kingston

Kingston

Simon

Rp1.567.408

Rp1.755.496 total

includes taxes & fees

4 Oct - 5 Oct

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

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

20. Changing Times Boutique Country Lodging

Craryville

Thomas

Rp3.580.600

Rp4.010.272 total

includes taxes & fees

28 Sept - 29 Sept

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Stay near popular Pine Plains attractions

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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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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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

Beekman Arms and Delamater Inn

10/10 Excellent

"The bartender she is excellent"

Quality Inn Great Barrington

10/10 Excellent

"A clean, well maintained, close to everything, motel. Would highly recommend and will stay again next time we are in the area."

Quality Inn Hyde Park Poughkeepsie North

8/10 Good

"A clean, well maintained hotel in an excellent location in Hyde Park."

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

10/10 Excellent

"Gorgeous view! Beautiful hotel, will be back!"

Courtyard by Marriott Kingston

10/10 Excellent

"I enjoyed my stay very much. It was very clean and very convenient. I have no complaints whatsoever"

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"Excellent place"

Mirbeau Inn & Spa

10/10 Excellent

"Beautiful property, relaxing spa, clean, great food. Would stay again!"

Pocketbook Hotel and Bath

10/10 Excellent

"Lovely. Staff was very helpful and friendly. The rooms were well appointed. We arrived at night and it was a little difficult finding the main entrance but obviously we succeeded"

Inn at Pine Plains

10/10 Excellent

"I had a lovely stay! Plan to return another time."

More cheap stays in Pine Plains

Quality Inn Hyde Park Poughkeepsie North

4142 Albany Post Rd Hyde Park NY

Rp1.445.667

Rp1.635.411 total

19 Oct - 20 Oct

includes taxes & fees

8/10 Very good! (1,012 reviews)

Super 8 by Wyndham Kingston

487 Washington Ave Kingston NY

Rp1.567.408

Rp1.755.496 total

4 Oct - 5 Oct

includes taxes & fees

6.2/10 (1,007 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Rp1.810.888

Rp2.022.761 total

18 Oct - 19 Oct

includes taxes & fees

8.6/10 Excellent! (1,002 reviews)

Kingston Regency Inn

503 Washington Avenue Kingston NY

Rp2.309.487

Rp2.838.146 total

27 Sept - 28 Sept

includes taxes & fees

6/10 (59 reviews)

St. Charles Hotel

16 Park Place Hudson NY

Rp2.685.450

Rp3.034.559 total

1 Oct - 2 Oct

includes taxes & fees

6.8/10 (980 reviews)

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

Rp3.853.621

Rp5.163.808 total

26 Oct - 27 Oct

includes taxes & fees

Frequently asked questions

What's the best place for a stay in Pine Plains?

Based on our traveller data, Inn at Pine Plains is one of the top choices for your stay. This B&B offers free breakfast and free parking. Two other choices for your trip to the area are Beekman Arms and Delamater Inn and Quality Inn Great Barrington. See all available top hotels, or vacation rentals in Pine Plains.

If I need to cancel my hotel reservation in Pine Plains, will I receive a refund?

Yes! Most hotel room reservations are refundable provided that you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, you might still have the option to cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Pine Plains.

What's the best dog-friendly hotel in Pine Plains?

Inn at Pine Plains is a top dog-friendly B&B and offers pillowtop beds for its human guests. See more pet-friendly hotel accommodations in Pine Plains.

What are some hotels with pools in Pine Plains?

Pocketbook Hotel and Bath: Features a steam room, 3 indoor swimming pools and spa services. Courtyard by Marriott Kingston and Kingston Regency Inn are two additional hotels with an on-site pool. View all hotels with pools in Pine Plains.

What is staying in Pine Plains like?

Travellers to Pine Plains will find plenty to explore and enjoy. In Pine Plains, there are 33 hotels and other accommodation options to choose from. Find out more about Pine Plains.

What should I see while I'm in Pine Plains?

The picturesque setting of Thompson Pond and Stissing Lake Park exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are The Stissing Center and Pine Plains Library. Take a look at what more there is to see and do in Expedia's Pine Plains guide.

What's the seasonal weather like in Pine Plains?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Pine Plains are January, February, March and April, with each month seeing an average of 17 cm of snowfall.

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Book Hotels in Pine Plains on Expedia.com

Find hotels in Pine Plains, NY from Rp1.367.789

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Pine Plains

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Pine Plains hotels

1. Inn at Pine Plains

2. the Alander

3. Residence Inn by Marriott Kingston

4. Beekman Arms and Delamater Inn

5. The Millerton Inn

6. Interlaken Inn & Resort

7. Kingston Regency Inn

8. Howard Johnson by Wyndham Saugerties

9. Little Cat Lodge

10. Courtyard by Marriott Kingston

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

12. The White Hart

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

14. Hampton Inn Kingston

15. Quality Inn Great Barrington

16. Locust Tree Bed and Breakfast LLC

17. Blackberry River Inn

18. Red Ranch Motel

19. Super 8 by Wyndham Kingston

20. Changing Times Boutique Country Lodging

Stay near popular Pine Plains attractions

Thompson Pond

Stissing Lake Park

The Stissing Center

Gallatin Town Hall

Pine Plains Library

Learn more about Pine Plains

Top Pine Plains Hotel Reviews

Beekman Arms and Delamater Inn

Quality Inn Great Barrington

Quality Inn Hyde Park Poughkeepsie North

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Courtyard by Marriott Kingston

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Mirbeau Inn & Spa

Pocketbook Hotel and Bath

Inn at Pine Plains

More cheap stays in Pine Plains

Quality Inn Hyde Park Poughkeepsie North

Super 8 by Wyndham Kingston

Quality Inn Great Barrington

Kingston Regency Inn

St. Charles Hotel

Pocketbook Hotel and Bath

Frequently asked questions

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