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Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
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Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Pine Plains

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

1. Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (318 reviews)
"good location/ walkable to down town !"
United States
teresina
The price is CA $324
CA $366 total
includes taxes & fees
Nov 16 - Nov 17
Inn at Pine Plains
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

2. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is CA $252
CA $995 total
includes taxes & fees
Nov 9 - Nov 10
NEW: Chic Modern Barn Style Home in Fun Area
A modern kitchen with white cabinets, a large island, and a skylight.

3. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"Stayed with a group for Millbrook Horse Trials, we had an amazing weekend at this calm and relaxing home with plenty of beds and amenities! What a treat!"
United States
Marianne R.
The price is CA $1,244
CA $1,954 total
includes taxes & fees
Nov 7 - Nov 8
A Country Lodge Straight Out of the Pages of a Great Novel
A modern bedroom with a large bed, a red sofa, a fireplace, and a television.

4. The Harlow House

The Harlow House
2.0 star property
Rhinebeck
8.8 out of 10, Excellent, (23 reviews)
"Great place"
United States
Robert
The price is CA $271
CA $307 total
includes taxes & fees
Nov 12 - Nov 13
The Harlow House
A swimming pool with a glass ceiling, indoor seating, and a brick wall.

5. Kingston Regency Inn

Kingston Regency Inn
2.5 star property
Kingston
6.4 out of 10, (117 reviews)
"Good stay for the price."
United States
Colleen
The price is CA $157
CA $193 total
includes taxes & fees
Nov 12 - Nov 13
Kingston Regency Inn
A wooden cabin with a deck, large windows, and outdoor seating.

6. The Cozy Cat Motel

The Cozy Cat Motel
Copake Falls
The price is CA $188
CA $211 total
includes taxes & fees
Nov 8 - Nov 9
The Cozy Cat Motel
A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

7. the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (291 reviews)
"Super cute, fairly clean and such a lovely breakfast!"
United States
Luis
The price is CA $231
CA $258 total
includes taxes & fees
Nov 21 - Nov 22
the Alander
A buffet with various food items, including omelets and baked goods, served in metal containers.

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

Holiday Inn Express & Suites Kingston-Ulster by IHG
2.5 star property
Lake Katrine
9.4 out of 10, Exceptional, (1,002 reviews)
"The room was clean and spacious. The bathroom was suitable for elderly guests such as my mother. The buffet breakfast was excellent too"
United States
Timothy
The price is CA $154
CA $173 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Kingston-Ulster by IHG
An outdoor patio with a fire pit, seating, and a building in the background.

9. Courtyard by Marriott Kingston

Courtyard by Marriott Kingston
3.0 star property
Kingston
8.8 out of 10, Excellent, (1,001 reviews)
"Very nice hotel in a convenient area too."
United States
Yvette
The price is CA $153
CA $172 total
includes taxes & fees
Dec 2 - Dec 3
Courtyard by Marriott Kingston
A room with a view of a lake, a balcony with a table and chairs, and a sofa.

10. Rhinecliff Hotel

Rhinecliff Hotel
2.0 star property
Rhinecliff
9.6 out of 10, Exceptional, (69 reviews)
"Our stay at the Rhinecliff Hotel was great! The view is amazing and the hotel was wonderful. Our room was beautiful and clean and had all the amenities we needed (hair dryer, steamer, extra towels, etc.). Checking in and out of the hotel was so easy. Would definitely stay here again!"
United States
Laura
The price is CA $201
CA $227 total
includes taxes & fees
Dec 7 - Dec 8
Rhinecliff Hotel
A tented area with two wooden folding chairs and a table, a patterned rug, and a view of greenery and a white tent in the background.

11. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is CA $311
CA $380 total
includes taxes & fees
Nov 8 - Nov 9
Gatherwild Ranch
A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

12. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (127 reviews)
"A great place to stay!"
United States
Thomas
The price is CA $279
CA $313 total
includes taxes & fees
Nov 7 - Nov 8
Changing Times Boutique Country Lodging
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

13. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,001 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is CA $106
CA $118 total
includes taxes & fees
Nov 29 - Nov 30
Quality Inn Great Barrington
A garden with a variety of plants and flowers, a white picket fence, and a small table with chairs.

14. Millbrook Country House Bed & Breakfast

Millbrook Country House Bed & Breakfast
4.0 star property
Millbrook
9.0 out of 10, Wonderful, (86 reviews)
"the minute we arrived the host was helpful, and very nice. He even asked if we needed dinner reservations. The room was clean and pristine. the breakfast was excellent. the host was very cordial and helpful. would definitely recommend. would definitely stay again if in that area"
United States
kenneth
The price is CA $335
CA $379 total
includes taxes & fees
Nov 8 - Nov 9
Millbrook Country House Bed & Breakfast
A kitchen with wooden shelves, a sink, and a dining area with a table and chairs.

15. the suite @ barn & bike - private, bucolic, serene setting

the suite @ barn & bike - private, bucolic, serene setting
Red Hook
9.8 out of 10, Exceptional, (16 reviews)
"The host was great, we enjoyed the suite, it was perfect for our ski trip. Lots of food options near, ver accomating."
United States
William D.
The price is CA $278
CA $338 total
includes taxes & fees
Nov 22 - Nov 23
the suite @ barn & bike - private, bucolic, serene setting
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

16. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (155 reviews)
"Beyond amazing, we loved it so much!"
United States
Stacy
The price is CA $202
CA $226 total
includes taxes & fees
Dec 6 - Dec 7
Little Cat Lodge
A covered outdoor dining area with tables set for a meal, surrounded by columns and large windows.

17. Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn
3.5 star property
Rhinebeck Village
8.2 out of 10, Very good, (1,004 reviews)
"Wonderful stay."
United States
steven
The price is CA $150
CA $169 total
includes taxes & fees
Nov 15 - Nov 16
Beekman Arms and Delamater Inn
A Holiday Inn Express hotel with a covered entrance, multiple floors, and a brick facade.

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

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
2.5 star property
Saugerties
8.8 out of 10, Excellent, (825 reviews)
"The room was very clean and the staff were very courteous and helpful."
United States
Jacqueline
The price is CA $177
CA $199 total
includes taxes & fees
Nov 9 - Nov 10
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
A residential garden with a pathway leading to a house.

19. The Amelia

The Amelia
2.0 star property
Hudson
9.6 out of 10, Exceptional, (42 reviews)
"Enjoyed our stay"
United States
Divya
The price is CA $385
CA $435 total
includes taxes & fees
Dec 6 - Dec 7
The Amelia
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

20. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (941 reviews)
"Easy access to everywhere we went. Clean"
United States
Phillip
The price is CA $84
CA $93 total
includes taxes & fees
Nov 8 - Nov 9
Monument Mountain Motel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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
A rustic barn surrounded by autumn foliage on a hillside.

Top reviews in Pine Plains

A buffet with various food items, including omelets and baked goods, served in metal containers.
Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG

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

10/10 Excellent

Parfait pour une pause lors de trajet en voiture. Propre, accueillant , confortable. Personnel courtois et attenionné.
Canada
Martin
Reviewed November 5, 2026
Holiday Inn Express & Suites Kingston-Ulster by IHG

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