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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months
No exact matches found, but these alternatives could be just right

Recommended hotels in Pine Plains

Bed & Breakfast in Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (301)
"Great stay"
United Kingdom
Katherine
The price is AED 909
AED 1,028 total
includes taxes & fees
24 Dec - 25 Dec
Inn at Pine Plains

Pocketbook Hotel and Bath

2.0 star property
8.4 out of 10, Very Good, (10)
"lovely place!"
United States
Samyuktha
The price is AED 859
AED 1,137 total
includes taxes & fees
4 Jan - 5 January 2026
Pocketbook Hotel and Bath

Quality Inn Hyde Park Poughkeepsie North

2.5 star property
8.0 out of 10, Very Good, (1004)
"Clean, decent breakfast, and overall great for the price "
United States
Erik
The price is AED 248
AED 280 total
includes taxes & fees
5 Jan - 6 January 2026
Quality Inn Hyde Park Poughkeepsie North

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (707)
"Great hospitality "
United States
regina maria
The price is AED 393
AED 439 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Cabin in Catskill

2.0 star property
9.6 out of 10, Exceptional, (106)
"The hospitality and making sure our stay was enjoyable most of all our needs during the time being. "
United States
Yessica
The price is AED 400
AED 591 total
includes taxes & fees
15 Dec - 16 Dec
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Motel in Great Barrington

2.5 star property
9.0 out of 10, Wonderful, (804)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel

Quality Inn Great Barrington

2.5 star property
8.4 out of 10, Very Good, (1001)
"Clean room, nice location "
United States
Devron
The price is AED 278
AED 310 total
includes taxes & fees
23 Dec - 24 Dec
Quality Inn Great Barrington

Bed & Breakfast in East Canaan

3.0 star property
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is AED 386
AED 443 total
includes taxes & fees
24 Dec - 25 Dec
Locust Tree Bed and Breakfast LLC

Inn in Rhinebeck

3.5 star property
8.4 out of 10, Very Good, (800)
"Really enjoyed staying at this lovely property."
United States
Kenneth
The price is AED 365
AED 413 total
includes taxes & fees
1 Jan - 2 January 2026
Beekman Arms and Delamater Inn

Holiday Park in Saugerties

5.0 star property
9.0 out of 10, Wonderful, (439)
"Great location. Amazing views. "
United States
Sarig
The price is AED 559
AED 770 total
includes taxes & fees
17 Dec - 18 Dec
AutoCamp Catskills

Residence Inn by Marriott Kingston

3.0 star property
8.8 out of 10, Excellent, (789)
"Very nice stay"
United States
LOIS
The price is AED 419
AED 469 total
includes taxes & fees
1 Jan - 2 January 2026
Residence Inn by Marriott Kingston

Hampton Inn Kingston

2.5 star property
9.0 out of 10, Wonderful, (1000)
"Courteous staff, clean room, pleasant atmosphere, convenient location, and good free breakfast."
United States
Karen
The price is AED 408
AED 457 total
includes taxes & fees
1 Jan - 2 January 2026
Hampton Inn Kingston

Courtyard by Marriott Kingston

3.0 star property
8.8 out of 10, Excellent, (1000)
"Great stay!!"
United States
Anita
The price is AED 403
AED 451 total
includes taxes & fees
28 Dec - 29 Dec
Courtyard by Marriott Kingston

Nautical Nest

2.5 star property
9.6 out of 10, Exceptional, (125)
"Very cute, great location in town, nice and quiet"
United States
Michael
The price is AED 436
AED 506 total
includes taxes & fees
5 Jan - 6 January 2026
Nautical Nest

Holiday Inn Express & Suites Kingston-Ulster by IHG

2.5 star property
9.4 out of 10, Exceptional, (1000)
"Great stay"
United States
Siju
The price is AED 422
AED 473 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Kingston-Ulster by IHG

Prospect Berkshires

3.0 star property
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 AED 955
AED 1,190 total
includes taxes & fees
17 Dec - 18 Dec
Prospect Berkshires

Howard Johnson by Wyndham Saugerties

2.0 star property
7.6 out of 10, Good, (1002)
"Easy check in, friendly staff. "
United States
Daniel
The price is AED 382
AED 428 total
includes taxes & fees
14 Dec - 15 Dec
Howard Johnson by Wyndham Saugerties

Lodge in Copake

2.5 star property
9.0 out of 10, Wonderful, (187)
"The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!"
United States
Jenna
The price is AED 514
AED 576 total
includes taxes & fees
16 Dec - 17 Dec
the Alander

The Nest Hudson

3.5 star property
9.6 out of 10, Exceptional, (210)
"What a beautiful stay right in the heart of Hudson. Cute, cozy, super clean with everything you need! "
United States
Kseniya
The Nest Hudson

Guesthouse in Kingston

3.5 star property
9.4 out of 10, Exceptional, (162)
"Great location."
United States
Catherine
The Wiltwyck
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pine Plains Hotel Reviews