Find Hotels with a Pool in Pine Plains, NY

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 availability on Pine Plains Hotels with a Pool

Top Pine Plains Hotels with a Pool

Prospect Berkshires
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers

Prospect Berkshires

3.0 star property
9.0 out of 10, Wonderful, (7)
"Gorgeous thoughtfully designed cabins with so many amenities/activities. Cliff house restaurant was delicious. Perfect getaway. "
The price is ₩417,248
₩513,867 total
includes taxes & fees
Nov 2 - Nov 3
Prospect Berkshires
Four Seasons Motel
Seasonal outdoor pool

Four Seasons Motel

2.0 star property
8.2 out of 10, Very Good, (198)
"Very cute and cozy little motel. They put a lot of effort into cleaning and decorating each room. "
The price is ₩142,649
₩154,061 total
includes taxes & fees
Oct 13 - Oct 14
Four Seasons Motel
Blackberry River Inn
Seasonal outdoor pool

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (142)
"Loved everything especially Lucas and Joe💟☮️"
The price is ₩234,444
₩269,611 total
includes taxes & fees
Oct 14 - Oct 15
Blackberry River Inn
Little Cat Lodge
Seasonal outdoor pool

Little Cat Lodge

2.0 star property
9.4 out of 10, Exceptional, (60)
"Atmosphere, service and food was excellent. Definitely going back!"
The price is ₩242,646
₩271,764 total
includes taxes & fees
Oct 13 - Oct 14
Little Cat Lodge
The Amelia
Seasonal outdoor pool, pool umbrellas, sun loungers

The Amelia

2.0 star property
10.0 out of 10, Exceptional, (24)
"Beautiful hotel, great service. Loved the fresh baked goodies a s"
The price is ₩409,545
₩462,786 total
includes taxes & fees
Nov 2 - Nov 3
The Amelia
Interlaken Inn & Resort
Seasonal outdoor pool

Interlaken Inn & Resort

3.5 star property
8.2 out of 10, Very Good, (265)
"The staff is courteous and accommodating especially the restaurant staff."
The price is ₩319,676
₩367,627 total
includes taxes & fees
Oct 26 - Oct 27
Interlaken Inn & Resort
Cornwall Inn and Lodge
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

Cornwall Inn and Lodge

3.0 star property
9.2 out of 10, Wonderful, (148)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
The price is ₩283,872
₩326,453 total
includes taxes & fees
Nov 1 - Nov 2
Cornwall Inn and Lodge
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (671)
"The staff was friendly and helpfull. The property was clean and functional."
The price is ₩147,214
₩164,432 total
includes taxes & fees
Nov 10 - Nov 11
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Courtyard by Marriott Kingston
Indoor pool

Courtyard by Marriott Kingston

3.0 star property
8.8 out of 10, Excellent, (1001)
"Great customer service, friendly staff, knowledgeable "
The price is ₩161,935
₩181,366 total
includes taxes & fees
Nov 9 - Nov 10
Courtyard by Marriott Kingston
Comfort Inn Saugerties
Indoor pool

Comfort Inn Saugerties

2.5 star property
7.4 out of 10, Good, (696)
"Awesome"
The price is ₩181,863
₩203,688 total
includes taxes & fees
Nov 9 - Nov 10
Comfort Inn Saugerties
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

Top Pine Plains Hotel Reviews

Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

10/10 Excellent
"I was pleasantly surprised with how gorgeous this hotel was. My room was super clean. The fitness area along with the pool were beautiful. If I'm ever in the area again this is where I will be staying! "
Heather 1-night trip
Posted 3 days ago
Best Western Plus Kingston Hotel And Conference Center

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations with pools in Pine Plains?
Inn at Pine Plains: Provides a children's pool, an indoor pool, and buffet. Best Western Plus Kingston Hotel And Conference Center: Features a snack bar/deli, an indoor pool, and buffet. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Features a snack bar/deli, an indoor pool, and free self parking. AutoCamp Catskills: Features cooked-to-order, a seasonal outdoor pool, and free self parking. Quality Inn Hyde Park Poughkeepsie North: Offers full, an indoor pool, and complimentary wired internet access.
What is there to see and do in Pine Plains?
Surround yourself with nature at Stissing Lake Park. During your stay, check out sights such as The Stissing Center, Pine Plains Library, and Thompson Pond.
When is the best time to book a hotel with a pool in Pine Plains?
Taking into account the local weather in Pine Plains can help you maximize your time at the pool during your trip. 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.