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Hotels in Pine Plains

October 2026
6
November 2026

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This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Where to stay in Pine Plains?

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 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

Inn at Pine Plains
Pine Plains
$275
$311 total
includes taxes & fees
Oct 12 - Oct 13
Inn at Pine Plains
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 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.

2. Jenny's Country Manor

Jenny's Country Manor
Red Hook
$140
$158 total
includes taxes & fees
Oct 7 - Oct 8
Jenny's Country Manor
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 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.

3. the Alander

the Alander
Copake
$140
$157 total
includes taxes & fees
Nov 6 - Nov 7
the Alander
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.

4. Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn
Rhinebeck Village
$152
$172 total
includes taxes & fees
Oct 8 - Oct 9
Beekman Arms and Delamater Inn
A modern bedroom with a large bed, a red sofa, a fireplace, and a television.
A living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.
A window with a view of a forested area, a small potted plant, and a black kettle on the windowsill.
A wooden deck with wicker chairs and a small table, overlooking a forested area.

5. The Harlow House

The Harlow House
Rhinebeck
$218
$246 total
includes taxes & fees
Oct 8 - Oct 9
The Harlow House
An outdoor patio with a fire pit, seating, and umbrellas.
A bedroom with a bed, a sofa, a wooden bench, a window, and a door.
A long dining table set with multiple wine glasses, water glasses, and folded white napkins.
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.

6. The Millerton Inn

The Millerton Inn
Millerton
$279
$316 total
includes taxes & fees
Oct 13 - Oct 14
The Millerton Inn
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 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.

7. Courtyard by Marriott Kingston

Courtyard by Marriott Kingston
Kingston
$127
$142 total
includes taxes & fees
Oct 25 - Oct 26
Courtyard by Marriott Kingston
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 modern building with multiple windows and a landscaped area with decorative pumpkins and a tree.
A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.

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

Holiday Inn Express & Suites Kingston-Ulster by IHG
Lake Katrine
$139
$156 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express & Suites Kingston-Ulster by IHG
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.

9. Rhinebeck Village Inn

Rhinebeck Village Inn
Rhinebeck Village
$119
$135 total
includes taxes & fees
Oct 26 - Oct 27
Rhinebeck Village Inn
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 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.

10. Interlaken Inn & Resort

Interlaken Inn & Resort
Lakeville
$229
$263 total
includes taxes & fees
Oct 26 - Oct 27
Interlaken Inn & Resort
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
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 wooden fire pit surrounded by six Adirondack chairs in a forested area.
A house with a stone patio and wooden stools.

11. Little Cat Lodge

Little Cat Lodge
Copake Falls
$169
$189 total
includes taxes & fees
Nov 2 - Nov 3
Little Cat Lodge
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.

12. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
Craryville
$200
$224 total
includes taxes & fees
Oct 7 - Oct 8
Changing Times Boutique Country Lodging
A house with a brick pathway leading to the front door, surrounded by lush greenery and trees.
A cozy living room with a fireplace, wooden floors, and a comfortable seating area.
A kitchen with a checkered floor, wooden cabinets, a white refrigerator, and hanging plants.
A red barn with a small window, surrounded by lush greenery and trees.

13. it's a good thing

it's a good thing
Clinton Corners
$179
$203 total
includes taxes & fees
Oct 7 - Oct 8
it's a good thing
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
A hotel room with a wooden dresser, a television, a microwave, and a mirror.
A row of white plastic chairs on a covered outdoor area with a white building in the background.
A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

14. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
$67
$74 total
includes taxes & fees
Nov 1 - Nov 2
Monument Mountain Motel
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 two-story white house with a front porch, a red door, and a well-maintained lawn.
A garden with various plants and flowers, a white fence, and outdoor furniture.

15. Millbrook Country House Bed & Breakfast

Millbrook Country House Bed & Breakfast
Millbrook
$240
$272 total
includes taxes & fees
Oct 8 - Oct 9
Millbrook Country House Bed & Breakfast
A modern kitchen with a built-in oven, microwave, and stainless steel range hood.
A hallway with a staircase, a framed painting, a mirror, and a potted plant.
A two-story building with a brick facade and a flat roof.
A modern interior with a round mirror reflecting a dining area, a large vase, and a guitar.

16. Howard Hotel

Howard Hotel
Hudson
$102
$116 total
includes taxes & fees
Nov 2 - Nov 3
Howard Hotel
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.
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'.
A hotel room with a bathroom, a bed, a desk, and a nightstand.

17. Quality Inn Great Barrington

Quality Inn Great Barrington
Great Barrington
$76
$85 total
includes taxes & fees
Nov 1 - Nov 2
Quality Inn Great Barrington
A spacious lobby with a fireplace, comfortable seating, and large windows.
An outdoor patio with a fire pit, wicker furniture, and a red building in the background.
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.

18. Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston
Kingston
$143
$160 total
includes taxes & fees
Nov 1 - Nov 2
Residence Inn by Marriott Kingston
A landscaped garden with coniferous trees and a bed of yellow flowers.
A compact kitchenette with a microwave, a small refrigerator, and a flat-screen TV mounted on the wall.
Point of interest
A flat-screen TV mounted on a wall above a wooden countertop.

19. Hudson Valley 9w Motel

Hudson Valley 9w Motel
Lake Katrine
$95
$156 total
includes taxes & fees
Oct 11 - Oct 12
Hudson Valley 9w Motel
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Go beyond your typical stay in Pine Plains

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Condo
Condo
Our prices for hotels in Pine Plains are cheapest in September

Price trends for hotels in Pine Plains

Pricing is based on two traveler single night rates
View properties in October

October

High 15°C / low 7°C. Sunny most days.
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Top landmarks in Pine Plains

Thompson Pond

8.0/10 (1 review)
Why not relax on the waterfront and snap some great vacation pics at Thompson Pond when visiting Pine Plains.
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The Stissing Center

If you’re after a show while in the center of Pine Plains, you might want to get tickets at The Stissing Center. If you'd also like to explore some of the parks in Pine Plains, Stissing Lake Park is nearby.
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Stissing Lake Park

Stissing Lake Park is 0.8 mi (1.3 km) from central Pine Plains, why not stop by during your stay. If you like Stissing Lake Park, you'll love Northern Dutchess Botanical Gardens and Stanford Recreation Park, both just a short drive away.
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Gallatin Town Hall

Gallatin Town Hall is worth a visit, located 3.9 mi (6.3 km) from central Pine Plains.
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Pine Plains Library

Pine Plains Library is worth a visit when in central Pine Plains.
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Learn more about Pine Plains

Pine Plains is well-known for its attractions such as The Stissing Center and Thompson Pond.

See all hotels in Pine Plains
A rustic barn surrounded by autumn foliage on a hillside.

Check out reviews of Pine Plains hotels guests love

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 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.

Inn at Pine Plains

Inn at Pine Plains
Pine Plains

10/10 Exceptional

United States
Kevin
Inn at Pine Plains
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.

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
Craryville

10/10 Exceptional

United States
Kathleen
Changing Times Boutique Country Lodging
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 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.

the Alander

the Alander
Copake

10/10 Exceptional

United States
NORAIDA
the Alander
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
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 wooden fire pit surrounded by six Adirondack chairs in a forested area.
A house with a stone patio and wooden stools.

Little Cat Lodge

Little Cat Lodge
Copake Falls

10/10 Exceptional

United States
Elisabeth
Little Cat Lodge
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 modern building with multiple windows and a landscaped area with decorative pumpkins and a tree.
A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.

Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG
Lake Katrine

10/10 Exceptional

United States
Maria
Holiday Inn Express & Suites Kingston-Ulster by IHG
A modern kitchen with a built-in oven, microwave, and stainless steel range hood.
A hallway with a staircase, a framed painting, a mirror, and a potted plant.
A two-story building with a brick facade and a flat roof.
A modern interior with a round mirror reflecting a dining area, a large vase, and a guitar.

Howard Hotel

Howard Hotel
Hudson

10/10 Exceptional

United States
David
Howard Hotel
A room with a view of a lake, a balcony with a table and chairs, and a sofa.
A building with a yellow exterior, a door with a glass panel, a potted plant, and a sign indicating accessibility.
A bathroom with a freestanding bathtub, a window with blinds, and a towel rack.
A room with a flat-screen TV mounted on the wall, two brown armchairs, a woven rug, and a wooden floor.

Rhinecliff Hotel

Rhinecliff Hotel
Rhinecliff

10/10 Exceptional

United States
Sandra
Rhinecliff Hotel
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 spa area with a large rock centerpiece, multiple seating areas, and a skylight ceiling.
A building with a central entrance, multiple windows, and outdoor seating.

Mirbeau Inn & Spa

Mirbeau Inn & Spa
Rhinebeck Village

10/10 Exceptional

United States
Paula
Mirbeau Inn & Spa
A bedroom with a large bed, a chair, and a window with curtains.
A covered porch with a dining area, a sofa, and decorative wall art.
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.

The White Hart

The White Hart
Salisbury

10/10 Exceptional

United States
thomas
The White Hart
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
A wooden wall with a white pendant light fixture.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.
A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.

Prospect Berkshires

Prospect Berkshires
Egremont

10/10 Exceptional

United States
Emily
Prospect Berkshires
An outdoor patio with a fire pit, seating, and umbrellas.
A bedroom with a bed, a sofa, a wooden bench, a window, and a door.
A long dining table set with multiple wine glasses, water glasses, and folded white napkins.
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.

The Millerton Inn

The Millerton Inn
Millerton

10/10 Exceptional

United States
Tatiana
The Millerton Inn
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 two-story white house with a front porch, a red door, and a well-maintained lawn.
A garden with various plants and flowers, a white fence, and outdoor furniture.

Millbrook Country House Bed & Breakfast

Millbrook Country House Bed & Breakfast
Millbrook

10/10 Exceptional

United States
Anonymous traveler
Millbrook Country House Bed & Breakfast
A modern bedroom with a large bed, a red sofa, a fireplace, and a television.
A living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.
A window with a view of a forested area, a small potted plant, and a black kettle on the windowsill.
A wooden deck with wicker chairs and a small table, overlooking a forested area.

The Harlow House

The Harlow House
Rhinebeck

10/10 Exceptional

United States
Matthew
The Harlow House
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.

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn
Rhinebeck Village

10/10 Exceptional

United States
John
Beekman Arms and Delamater Inn
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 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.

Jenny's Country Manor

Jenny's Country Manor
Red Hook

10/10 Exceptional

United States
Elyssamay
Jenny's Country Manor
A spacious living area with a high ceiling, wooden beams, and large windows. There are multiple seating arrangements including a sofa, chairs, and a dining table.
A bed with white linens and a woven pillow, a window with a view of trees and a wooden structure, and a wall-mounted light fixture.
A modern interior with a wooden dining table, chairs, a sofa, and a bar area with wine bottles.
A modern house with a sloped roof, large windows, and a well-maintained lawn.

AutoCamp Catskills

AutoCamp Catskills
Saugerties

10/10 Exceptional

United States
Nickolas
AutoCamp Catskills

Frequently Asked Questions

What hotels do travelers recommend in Pine Plains?

Guests like Inn at Pine Plains.

Can I book a refundable hotel in Pine Plains?

If you want the flexibility to change your travel plans to Pine Plains, most accommodations offer refundable* bookable rates. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Pine Plains if I want a vacation rental instead of a hotel?

If you want to find a good alternative to a hotel, review our selection of 23 vacation homes.

What will the weather in Pine Plains be like during my visit?

The warmest months in Pine Plains are usually July and August with an average temp of 67°F. January and February are the chilliest months when the average temp is 29°F. The rainiest months are October and August.

Why should I book my Pine Plains hotel with Hotels.com?

There are plenty of reasons to book your Pine Plains travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.