Search Chalets in Pine Plains

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Chalets in Pine Plains

No exact matches found, but these alternatives could be just right

Recommended hotels in Pine Plains

Property entrance
Inn at Pine Plains

Inn at Pine Plains

3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (300)
"Great stay"
United Kingdom
Katherine
The price is SAR 929
SAR 1,050 total
includes taxes & fees
3 Dec - 4 Dec
Inn at Pine Plains
Exterior
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, (1007)
"Great stay"
United States
Siju
The price is SAR 387
SAR 434 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Kingston-Ulster by IHG
Gazebo
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

2.0 star property
Saugerties
7.6 out of 10, Good, (1005)
"we found the room very clean and the staff was friendly "
United States
MAURICIO
The price is SAR 332
SAR 371 total
includes taxes & fees
7 Dec - 8 Dec
Howard Johnson by Wyndham Saugerties
Exterior
Monument Mountain Motel

Monument Mountain Motel

2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (801)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Exterior
Hampton Inn Kingston

Hampton Inn Kingston

2.5 star property
Kingston
9.0 out of 10, Wonderful, (1008)
"Courteous staff, clean room, pleasant atmosphere, convenient location, and good free breakfast."
United States
Karen
The price is SAR 417
SAR 467 total
includes taxes & fees
11 Dec - 12 Dec
Hampton Inn Kingston
Exterior
Quality Inn

Quality Inn

2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1006)
"Clean room, nice location "
United States
Devron
The price is SAR 284
SAR 317 total
includes taxes & fees
15 Dec - 16 Dec
Quality Inn
Front of property
Courtyard by Marriott Kingston

Courtyard by Marriott Kingston

3.0 star property
Kingston
8.8 out of 10, Excellent, (1004)
"Great stay!!"
United States
Anita
The price is SAR 443
SAR 496 total
includes taxes & fees
4 Dec - 5 Dec
Courtyard by Marriott Kingston
Premium bedding, down comforters, Tempur-Pedic beds, in-room safe
AutoCamp Catskills

AutoCamp Catskills

5.0 star property
Saugerties
9.0 out of 10, Wonderful, (438)
"Great location. Amazing views. "
United States
Sarig
The price is SAR 611
SAR 832 total
includes taxes & fees
15 Dec - 16 Dec
AutoCamp Catskills
Dinner served, American cuisine
the Alander

the Alander

2.5 star property
Copake
9.0 out of 10, Wonderful, (184)
"Very nice clean place in a beautiful area. "
United States
Wayne
The price is SAR 525
SAR 588 total
includes taxes & fees
3 Dec - 4 Dec
the Alander
Front of property
The Wiltwyck

The Wiltwyck

3.5 star property
Kingston
9.4 out of 10, Exceptional, (162)
"Great location."
United States
Catherine
The Wiltwyck
Exterior
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, (702)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
The price is SAR 401
SAR 448 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Aerial view
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 SAR 394
SAR 453 total
includes taxes & fees
4 Dec - 5 Dec
Locust Tree Bed and Breakfast LLC
Front of property
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2.0 star property
Hudson
8.8 out of 10, Excellent, (6)
"The room was very nice, and the staff was great"
United States
Kienan
The price is SAR 780
SAR 1,051 total
includes taxes & fees
16 Dec - 17 Dec
Pocketbook Hotel and Bath
View from property
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3.0 star property
Kingston
8.8 out of 10, Excellent, (784)
"Very nice stay"
United States
LOIS
The price is SAR 416
SAR 466 total
includes taxes & fees
1 Jan - 2 January 2026
Residence Inn by Marriott Kingston
Exterior
The Brooks Motel

The Brooks Motel

2.0 star property
Hillsdale
7.6 out of 10, Good, (117)
"Everything was lovely, thanks. Small note: the toilet seat needs a bolt on one side. Otherwise everything was great! Thx"
United States
Savannah
The Brooks Motel
Front of property
Little Cat Lodge

Little Cat Lodge

2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (65)
"This is a very cute lodge, updated with a bit of vintage charm. Close to all the Berkshires must sees and nature hiking trails. "
United States
Kayla
Little Cat Lodge
View from property
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 SAR 975
SAR 1,215 total
includes taxes & fees
8 Dec - 9 Dec
Prospect Berkshires
Terrace/patio
Nautical Nest

Nautical Nest

2.5 star property
Hudson
9.6 out of 10, Exceptional, (123)
"We had an amazing stay! What a lovely and comfortable room, conveniently situated to shopping & so many great dining options. The shared kitchen area was well-appreciated. We would definitely return again in the future. "
United States
Robin
The price is SAR 428
SAR 496 total
includes taxes & fees
8 Dec - 9 Dec
Nautical Nest
Terrace/patio
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, (1011)
"Nice staff, clean room, breakfast was tasty."
United States
Sarah
The price is SAR 366
SAR 410 total
includes taxes & fees
8 Dec - 9 Dec
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.
View all properties

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pine Plains Hotel Reviews

Beekman Arms Hotel

Beekman Arms Hotel

10/10 Excellent
"The general manager was warm and welcoming, our room was cozy and comfortable, and the inn was centrally located. We will definitely be back!"
Nancy 2-night trip
Posted 1 day ago
Beekman Arms Hotel