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

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

1. Inn at Pine Plains

Pine Plains

teresina

Rp4.917.550

Rp5.562.978 total

includes taxes & fees

6 Oct - 7 Oct

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

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

A staircase with ornate black railings and a large chandelier.

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

2. Mirbeau Inn & Spa

Rhinebeck Village

Maria

Rp7.281.550

Rp8.237.343 total

includes taxes & fees

4 Nov - 5 Nov

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

A wooden interior with a barrel and a wine rack.

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

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

3. Beekman Arms and Delamater Inn

Rhinebeck Village

Victoria and Scott

Rp2.400.658

Rp2.715.745 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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 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

Thomas

Rp2.583.949

Rp2.894.023 total

includes taxes & fees

6 Oct - 7 Oct

A hotel room with a bed, two bedside tables, a desk with a chair, a small armchair, and a floor lamp.

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

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

A tented area with lush greenery and a dining setup.

5. Interlaken Inn & Resort

Lakeville

Stacie

Rp3.562.094

Rp4.096.409 total

includes taxes & fees

26 Oct - 27 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.

6. Diamond Mills Resort

Saugerties

Rp4.752.678

Rp5.769.985 total

includes taxes & fees

6 Oct - 7 Oct

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

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

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.

7. Courtyard by Marriott Kingston

Kingston

Ana

Rp2.264.755

Rp2.536.525 total

includes taxes & fees

25 Oct - 26 Oct

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.

8. The Millerton Inn

Millerton

Chelsy

Rp4.490.170

Rp5.079.506 total

includes taxes & fees

6 Oct - 7 Oct

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

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.

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

9. The White Hart

Salisbury

William

Rp8.054.947

Rp9.263.234 total

includes taxes & fees

7 Oct - 8 Oct

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

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.

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

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

Lake Katrine

Cindy

Rp2.467.716

Rp2.763.840 total

includes taxes & fees

2 Nov - 3 Nov

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 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.

11. Residence Inn by Marriott Kingston

Kingston

Lamisa

Rp2.557.126

Rp2.863.981 total

includes taxes & fees

1 Nov - 2 Nov

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.

An arched stone structure with windows, surrounded by trees and a clear sky.

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

12. Hutton Brickyards Riverfront Hotel + Venue

Kingston

Georgiann

Rp4.090.507

Rp5.117.830 total

includes taxes & fees

6 Oct - 7 Oct

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

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

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

A living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

13. The Harlow House

Rhinebeck

Lauren

Rp3.974.453

Rp4.496.100 total

includes taxes & fees

3 Nov - 4 Nov

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

A bedroom with two single beds, a nightstand with a lamp, a wooden chair, a door, and a wall-mounted light fixture.

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

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

14. Jenny's Country Manor

Red Hook

amanda

Rp2.503.480

Rp2.832.151 total

includes taxes & fees

6 Oct - 7 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 traditional living room with a fireplace, floral patterned sofa, and a patterned rug.

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

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

15. Changing Times Boutique Country Lodging

Craryville

Thomas

Rp3.576.400

Rp4.005.568 total

includes taxes & fees

6 Oct - 7 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 Quality Inn sign, a brick building, and a parking lot with cars.

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

16. Quality Inn Great Barrington

Great Barrington

Joan

Rp1.344.369

Rp1.501.660 total

includes taxes & fees

1 Nov - 2 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".

17. Hampton Inn Kingston

Kingston

stephen

Rp2.434.098

Rp2.726.190 total

includes taxes & fees

2 Nov - 3 Nov

A stone building with a wooden staircase and a garden with white flowers.

A spacious hotel room with a large bed, a sitting area with a sofa and chairs, a dining table, and a kitchen area with cabinets and a coffee machine.

A room with a hanging rattan chair, a wooden sofa, a small round table, and a ceiling fan. Large windows provide views of greenery outside.

A garden pathway surrounded by various flowering plants and a wooden structure in the background.

18. Troutbeck

Amenia

Charles

Rp9.195.818

Rp11.118.049 total

includes taxes & fees

3 Nov - 4 Nov

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

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.

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

19. Millbrook Country House Bed & Breakfast

Millbrook

kenneth

Rp4.291.680

Rp4.854.963 total

includes taxes & fees

8 Oct - 9 Oct

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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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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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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

Prospect Berkshires

10/10 Excellent

"Absolutely spectacular resort! Could not have enjoyed more."

Quality Inn Great Barrington

8/10 Good

"The cleaning staff were friendly and helpful!"

Quality Inn Hyde Park Poughkeepsie North

8/10 Good

"Room was clean... Bed/ Sheets were comfortable. Close to Vanderbilt National Park and probably cleanest and most affordable option near Rhinebeck and the great restaurants on the area. Bathroom fixtures could use some updates."

Super 8 by Wyndham Kingston

8/10 Good

"A great place to spend the weekend visiting family near by."

Howard Johnson by Wyndham Saugerties

10/10 Excellent

"The room was clean and staff very pleasant and helpful. I would stay again."

Residence Inn by Marriott Kingston

10/10 Excellent

"Very nice spot"

AutoCamp Catskills

10/10 Excellent

"Absolutely loved our stay! The area is beautiful, the property is amazing and so well-maintained, and the friendly staff. This was our first time staying in a premium Airstream for both me and my hubby, and we were honestly amazed very clean too! Such a fun, unique, and awesome experience."

Courtyard by Marriott Kingston

10/10 Excellent

"Awesome hotel. Staff is amazing and room was so comfortable."

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

Rp1.291.975

Rp1.461.546 total

2 Nov - 3 Nov

includes taxes & fees

8/10 Very good! (1,004 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Rp1.344.369

Rp1.501.660 total

1 Nov - 2 Nov

includes taxes & fees

8.6/10 Excellent! (1,003 reviews)

Super 8 by Wyndham Kingston

487 Washington Ave Kingston NY

Rp1.504.770

Rp1.685.343 total

4 Nov - 5 Nov

includes taxes & fees

6.2/10 (1,003 reviews)

Kingston Regency Inn

503 Washington Avenue Kingston NY

Rp2.253.132

Rp2.768.755 total

2 Nov - 3 Nov

includes taxes & fees

St. Charles Hotel

16 Park Place Hudson NY

Rp2.682.300

Rp3.030.999 total

6 Oct - 7 Oct

includes taxes & fees

6.6/10 (988 reviews)

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

Rp3.332.654

Rp4.574.165 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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Find hotels in Pine Plains, NY from Rp1.461.546

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. Mirbeau Inn & Spa

3. Beekman Arms and Delamater Inn

4. the Alander

5. Interlaken Inn & Resort

6. Diamond Mills Resort

7. Courtyard by Marriott Kingston

8. The Millerton Inn

9. The White Hart

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

11. Residence Inn by Marriott Kingston

12. Hutton Brickyards Riverfront Hotel + Venue

13. The Harlow House

14. Jenny's Country Manor

15. Changing Times Boutique Country Lodging

16. Quality Inn Great Barrington

17. Hampton Inn Kingston

18. Troutbeck

19. Millbrook Country House Bed & Breakfast

Stay near popular Pine Plains attractions

Thompson Pond

The Stissing Center

Stissing Lake Park

Gallatin Town Hall

Pine Plains Library

Learn more about Pine Plains

Top Pine Plains Hotel Reviews

Prospect Berkshires

Quality Inn Great Barrington

Quality Inn Hyde Park Poughkeepsie North

Super 8 by Wyndham Kingston

Howard Johnson by Wyndham Saugerties

Residence Inn by Marriott Kingston

AutoCamp Catskills

Courtyard by Marriott Kingston

Interlaken Inn & Resort

More cheap stays in Pine Plains

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Great Barrington

Super 8 by Wyndham Kingston

Kingston Regency Inn

St. Charles Hotel

Pocketbook Hotel and Bath

Frequently asked questions

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