Find hotels in Pine Plains, NY from ￥13,484

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Dec 15 - Dec 16
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Dec 16 - Dec 17
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Dec 19 - Dec 21
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Our top choices for Pine Plains hotels

Free daily continental breakfast
Inn at Pine Plains

Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (302)
"Great stay"
United Kingdom
Katherine
The price is ￥38,563
￥43,625 total
includes taxes & fees
Dec 16 - Dec 17
Inn at Pine Plains
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (707)
"Great hospitality "
United States
regina maria
The price is ￥16,672
￥18,623 total
includes taxes & fees
Dec 17 - Dec 18
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior
Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North
2.5 star property
Hyde Park
8.0 out of 10, Very Good, (1005)
"Clean, decent breakfast, and overall great for the price "
United States
Erik
The price is ￥11,919
￥13,484 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Quality Inn Hyde Park Poughkeepsie North
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (805)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Mini-fridge, stovetop, cookware/dishes/utensils, paper towels
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (108)
"The hospitality and making sure our stay was enjoyable most of all our needs during the time being. "
United States
Yessica
The price is ￥18,541
￥26,755 total
includes taxes & fees
Dec 16 - Dec 17
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Lobby
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1003)
"Clean room, nice location "
United States
Devron
The price is ￥11,787
￥13,165 total
includes taxes & fees
Dec 28 - Dec 29
Quality Inn Great Barrington
Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is ￥16,360
￥18,814 total
includes taxes & fees
Dec 16 - Dec 17
Locust Tree Bed and Breakfast LLC
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is ￥32,703
￥41,750 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Prospect Berkshires
Front of property
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn
3.5 star property
Rhinebeck
8.4 out of 10, Very Good, (806)
"I’ve stayed at the Beckman Arms many times, in all of the various parts (motel, Delamater House, etc) and have never been disappointed. The location is exceptional, the rooms are cozy and clean, and parking is great. I highly recommend it if you’re staying in the area."
United States
Armand
The price is ￥15,803
￥17,878 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Beekman Arms and Delamater Inn
Corner Studio | In-room safe, blackout drapes, iron/ironing board, free WiFi
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
2.0 star property
Hudson
8.4 out of 10, Very Good, (10)
"lovely place!"
United States
Samyuktha
The price is ￥34,901
￥46,481 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Pocketbook Hotel and Bath
View from property
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston
3.0 star property
Kingston
8.8 out of 10, Excellent, (790)
"Very nice stay"
United States
LOIS
The price is ￥17,762
￥19,892 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Residence Inn by Marriott Kingston
Free daily continental breakfast
Holiday Inn Express & Suites Kingston-Ulster by IHG

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, (1002)
"Great stay"
United States
Siju
The price is ￥17,918
￥20,068 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express & Suites Kingston-Ulster by IHG
Front of property
Courtyard by Marriott Kingston

Courtyard by Marriott Kingston

Courtyard by Marriott Kingston
3.0 star property
Kingston
8.8 out of 10, Excellent, (1002)
" Lean room, quiet location and comfortable bed."
United States
Barbara
The price is ￥17,085
￥19,134 total
includes taxes & fees
Dec 21 - Dec 22
Courtyard by Marriott Kingston
Reception
Hampton Inn Kingston

Hampton Inn Kingston

Hampton Inn Kingston
2.5 star property
Kingston
9.0 out of 10, Wonderful, (1002)
"Everything was amazing! The room was great and the staff is superb!"
United States
Danielle
The price is ￥17,326
￥19,405 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn Kingston
Premium bedding, down comforters, Tempur-Pedic beds, in-room safe
AutoCamp Catskills

AutoCamp Catskills

AutoCamp Catskills
5.0 star property
Saugerties
9.0 out of 10, Wonderful, (441)
"Great location. Amazing views. "
United States
Sarig
The price is ￥23,699
￥32,651 total
includes taxes & fees
Dec 18 - Dec 19
AutoCamp Catskills
Restaurant
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
2.0 star property
Saugerties
7.6 out of 10, Good, (1004)
"Easy check in, friendly staff. "
United States
Daniel
The price is ￥16,204
￥18,148 total
includes taxes & fees
Dec 21 - Dec 22
Howard Johnson by Wyndham Saugerties
Premium bedding, memory foam beds, individually decorated
Nautical Nest

Nautical Nest

Nautical Nest
2.5 star property
Hudson
9.6 out of 10, Exceptional, (125)
"Very cute, great location in town, nice and quiet"
United States
Michael
The price is ￥18,510
￥21,470 total
includes taxes & fees
Dec 16 - Dec 17
Nautical Nest
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (758)
"Clean room, very courteous staff "
United States
Thomas
The price is ￥21,034
￥23,495 total
includes taxes & fees
Dec 21 - Dec 22
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Superior Suite | Living area | 32-inch Smart TV with digital channels, TV, Netflix
The Wiltwyck

The Wiltwyck

The Wiltwyck
3.5 star property
Kingston
9.4 out of 10, Exceptional, (163)
"Great location."
United States
Catherine
The Wiltwyck
Terrace/patio
Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center
2.5 star property
Kingston
7.6 out of 10, Good, (1004)
"Nice staff, clean room, breakfast was tasty."
United States
Sarah
The price is ￥15,204
￥17,028 total
includes taxes & fees
Dec 22 - Dec 23
Best Western Plus Kingston Hotel And Conference Center
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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Stay near popular Pine Plains attractions

The Stissing Center

You can get tickets for a performance at The Stissing Center on your trip to Pine Plains.
See properties

Stissing Lake Park

Explore the great outdoors at Stissing Lake Park, a lovely green space in Pine Plains.
See properties

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
Sharon Ct, USA Fall foliage and autumn colors.

Top Pine Plains Hotel Reviews

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"Everything has exceeded expectations!!!"
Angela 1-night trip
Posted 2 days ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

More cheap stays in Pine Plains

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

4142 Albany Post Rd Hyde Park NY
The price is ￥11,919 per night from Jan 5 to Jan 6
￥11,919
￥13,484 total
Jan 5 - Jan 6, 2026
includes taxes & fees
8/10 Very Good! (1,005 reviews)

Frequently asked questions

What's the best place for a stay in Pine Plains?
Based on our traveler 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 Residence Inn by Marriott Kingston and AutoCamp Catskills. See all available top hotels, or vacation rentals in Pine Plains.
What's the top vacation rental in Pine Plains?
Esopus Creek modern Tiny house Retreat!: This vacation home near Pine Plains is located on a river and has a fireplace, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. See all vacation rentals in Pine Plains.
If I need to cancel my hotel reservation in Pine Plains, will I receive a refund?
Yes! Most room reservations are refundable if you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Pine Plains.
Where can I learn more about changing or cancelling my trip to Pine Plains?
For more information about updating your trip to Pine Plains or cancelling it, head over to our customer service page.
What's the best pet-friendly accommodation 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?
Hampton Inn Kingston: Offers a snack bar/deli, an indoor pool, and buffet. Best Western Plus Kingston Hotel And Conference Center and Courtyard by Marriott Kingston are two additional hotels that feature an onsite pool. View all hotels with pools in Pine Plains.
What is the best accommodation for staying close to Columbia County Airport (HCC)?
St. Charles Hotel is one of the top choices for your stay and is a popular hotel, featuring free breakfast and free WiFi. It's located 4.8 mi (7.8 km) from Columbia County Airport. Other good options close to the airport include Modern Farmhouse on 80 Acres and The Nest Hudson.
What is staying in Pine Plains like?
Travelers to Pine Plains will find plenty to explore and enjoy. In Pine Plains, there are 36 hotels and other accommodations to choose from. Find out more about Pine Plains.
What are the top places to visit in Pine Plains?
Favorite places to visit include The Stissing Center, Stissing Lake Park, and Pine Plains Library. A couple of additional sights to add to your agenda are Thompson Pond and Gallatin Town Hall. Check out what more to see and do in Expedia's Pine Plains guide.
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.

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