Search Resort Hotels in Pine Plains from CA $84

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10
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 $388
CA $439 total
includes taxes & fees
Nov 11 - Nov 12
Inn at Pine Plains
A spacious living area with a sofa, dining table, and chairs, a fireplace, and large windows.

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 $292
CA $1,061 total
includes taxes & fees
Nov 12 - Nov 13
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 $1,257
CA $1,974 total
includes taxes & fees
Nov 13 - Nov 14
A Country Lodge Straight Out of the Pages of a Great Novel
A wooden cabin with a deck, large windows, and outdoor seating.

4. The Cozy Cat Motel

The Cozy Cat Motel
Copake Falls
The price is CA $171
CA $191 total
includes taxes & fees
Nov 11 - Nov 12
The Cozy Cat Motel
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
6.6 out of 10, (129 reviews)
"Good stay for the price."
United States
Colleen
The price is CA $159
CA $195 total
includes taxes & fees
Nov 24 - Nov 25
Kingston Regency Inn
A modern bedroom with a large bed, a red sofa, a fireplace, and a television.

6. 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 $273
CA $309 total
includes taxes & fees
Nov 12 - Nov 13
The Harlow House
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.

7. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
10.0 out of 10, Exceptional, (1 review)
"Amazing sauna session"
United States
AYANO
The price is CA $315
CA $384 total
includes taxes & fees
Nov 11 - Nov 12
Gatherwild Ranch
An outdoor patio with a fire pit, seating, and a building in the background.

8. Courtyard by Marriott Kingston

Courtyard by Marriott Kingston
3.0 star property
Kingston
8.8 out of 10, Excellent, (1,004 reviews)
"Very nice hotel in a convenient area too."
United States
Yvette
The price is CA $155
CA $173 total
includes taxes & fees
Dec 2 - Dec 3
Courtyard by Marriott Kingston
A buffet with various food items, including omelets and baked goods, served in metal containers.

9. 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, (1,005 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 $160
CA $179 total
includes taxes & fees
Dec 9 - Dec 10
Holiday Inn Express & Suites Kingston-Ulster by IHG
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, (73 reviews)
"Hot tub was great! Amazing view"
United States
Carly
The price is CA $203
CA $229 total
includes taxes & fees
Dec 1 - Dec 2
Rhinecliff Hotel
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

11. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,005 reviews)
"Great location friendly staff"
United States
David
The price is CA $107
CA $119 total
includes taxes & fees
Dec 1 - Dec 2
Quality Inn Great Barrington
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

12. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (943 reviews)
"Clean, reasonably priced, convenient"
United States
Martha
The price is CA $85
CA $94 total
includes taxes & fees
Nov 11 - Nov 12
Monument Mountain Motel
A modern kitchen with a built-in oven, microwave, and stainless steel range hood.

13. Howard Hotel

Howard Hotel
2.0 star property
Hudson
9.8 out of 10, Exceptional, (221 reviews)
"Wonderful hotel"
United States
zehava
The price is CA $165
CA $187 total
includes taxes & fees
Nov 22 - Nov 23
Howard Hotel
A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

14. the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (292 reviews)
"Super cute, fairly clean and such a lovely breakfast!"
United States
Luis
The price is CA $198
CA $221 total
includes taxes & fees
Nov 11 - Nov 12
the Alander
A covered outdoor dining area with tables set for a meal, surrounded by columns and large windows.

15. Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn
3.5 star property
Rhinebeck Village
8.2 out of 10, Very good, (1,011 reviews)
"great place to stay"
United States
Julia
The price is CA $202
CA $229 total
includes taxes & fees
Nov 15 - Nov 16
Beekman Arms and Delamater Inn
A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

16. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (128 reviews)
"A great place to stay!"
United States
Thomas
The price is CA $282
CA $316 total
includes taxes & fees
Nov 11 - Nov 12
Changing Times Boutique Country Lodging
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

17. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (158 reviews)
"Such a lovely stay! Helpful and kind staff, and lots of nearby nature, farms, vineyards, and restaurants."
United States
Nutcha
The price is CA $202
CA $226 total
includes taxes & fees
Nov 17 - Nov 18
Little Cat Lodge
A kitchen with a stainless steel sink, a window with a view of a wooden deck and yellow chairs, and a door leading to an outdoor area.

18. The Nest Hudson

The Nest Hudson
3.5 star property
Hudson
9.6 out of 10, Exceptional, (251 reviews)
"The location is great! Walkable to main part of town. We were in Suite 1 so no stairs to carry up luggage. The room is very spacious and the bathroom nicely updated. Super clean. I would definitely book again if I’m in the area."
United States
Lisa
The price is CA $161
CA $186 total
includes taxes & fees
Nov 16 - Nov 17
The Nest Hudson
A Holiday Inn Express hotel with a covered entrance, multiple floors, and a brick facade.

19. 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, (831 reviews)
"Room was nice and spacious Breakfast was tasty done with a class and quick service"
United States
Artur
The price is CA $191
CA $213 total
includes taxes & fees
Dec 2 - Dec 3
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
A bedroom with a bed, bedside table, and a wall-mounted mirror.

20. Nautical Nest

Nautical Nest
2.5 star property
Hudson
9.4 out of 10, Exceptional, (156 reviews)
"Perfect place to stay in Hudson! Great location!"
United States
Christina
The price is CA $168
CA $195 total
includes taxes & fees
Nov 17 - Nov 18
Nautical Nest
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 modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.
the Alander

the Alander

the Alander
Copake

10/10 Excellent

Loved our stay, staff very attentive and helpful!!
Canada
Kelly
Reviewed May 24, 2025
the Alander

Frequently Asked Questions

What is Pine Plains like for a resort vacation?

Expedia can help you find resorts and other lodging options that provide similar amenities and comforts. If you have trouble finding a resort in Pine Plains that meets your needs, try using the search page filters to look for hotels, or search for properties with amenities like pools or all-inclusive options. We make it easy to book great accommodations so you can focus on creating your trip itinerary.

What can I do in Pine Plains?

Experience the local theater scene at The Stissing Center, or bring the kids to Dutchess County Fairgrounds for some family fun. Thompson Pond and Stissing Lake Park are a few additional attractions in the area that you might like.

What's the weather like in Pine Plains?

The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Pine Plains are January, February, March, and April, with each month seeing an average of 7 inches of snowfall.

What's the best way to get to and around Pine Plains?

Fly into Hudson, NY (HCC-Columbia County), which is located 21.9 mi (35.3 km) away from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.

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