A rural landscape with snow-covered fields, a winding road, and scattered trees.

Find Hotels with a Pool in Hillsdale, NY

  • 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 Hillsdale Hotels with a Pool

Tonight
Aug 24 - Aug 25
Tomorrow
Aug 25 - Aug 26
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Hillsdale hotels with a pool

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A house with a stone patio and wooden stools.
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.

1. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
NT$4,272
NT$4,785 total
includes taxes & fees
Aug 25 - Aug 26
Little Cat Lodge
An indoor swimming pool with clear water, surrounded by chairs and tables, large windows, and a tiled floor.
A modern hotel lobby with seating areas, tables, and a reception desk.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A buffet with labeled containers for omelets and other dishes.

2. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
  • Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
NT$3,919
NT$4,377 total
includes taxes & fees
Sep 23 - Sep 24
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A large house with a balcony and a grassy yard.
A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.
A two-story building with a gabled roof and a chimney.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

3. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
NT$3,584
NT$4,003 total
includes taxes & fees
Sep 1 - Sep 2
The Little Lion
A poolside area with lounge chairs and a pool.
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

4. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
NT$10,466
NT$12,758 total
includes taxes & fees
Sep 17 - Sep 18
Prospect Berkshires
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A hotel room with two beds, a desk, a television, and a dresser.
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

5. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
  • Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
NT$6,201
NT$6,927 total
includes taxes & fees
Aug 30 - Aug 31
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A backyard with a swimming pool, lounge chairs, and a hot tub.
A covered porch with wicker furniture and hanging flower baskets.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

6. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
NT$5,018
NT$7,188 total
includes taxes & fees
Sep 8 - Sep 9
The Red Lion Inn
A large indoor swimming pool with clear water, surrounded by walls with informational posters and a reception area with a 'Welcome' sign.
A multi-story hotel with balconies, a pond with rocks, and a clear sky.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

7. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
NT$3,728
NT$4,786 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Inn Club Vacations Oak 'n Spruce Resort

8. Berkshire Travel Lodge

Berkshire Travel Lodge
Austerlitz
  • Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
NT$2,150
NT$2,408 total
includes taxes & fees
Sep 1 - Sep 2
Berkshire Travel Lodge
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

9. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
NT$5,034
NT$5,623 total
includes taxes & fees
Sep 14 - Sep 15
The Yankee Inn
An indoor swimming pool with a concrete floor, a large window, and a vase with flowers.
A spacious room with leather seating, large windows, and exposed brick walls.
A restaurant with long tables, chairs, and a brick wall.
A bar area with wooden beams, a bar counter, and stools.

10. Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
Hudson
NT$7,140
NT$9,508 total
includes taxes & fees
Aug 31 - Sep 1
Pocketbook Hotel and Bath
View all properties

Choose what matters most at hotels with a pool in Hillsdale

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Hillsdale Hotel Reviews

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

10/10 Excellent
"Very great stay and cleanest!"
Nancy 1-night trip
Posted 1 day ago
Howard Johnson by Wyndham Saugerties
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"I liked the balcony overlooking the lake"
Rinat 3-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Luann 1-night trip
Posted 2 days ago
The Yankee Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 3 days ago
Howard Johnson by Wyndham Lenox

Frequently asked questions

What are some accommodations with pools in Hillsdale?
The Yankee Inn: Features a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge: Offers free self parking, an indoor pool, and complimentary wireless internet access. FairBridge Inn Express: Features buffet, an indoor pool, and complimentary wired internet access. Berkshires Untold: Offers 3 restaurants, an outdoor pool, and spa services. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Features free self parking, an outdoor pool, and flat-screen televisions.
What is there to see and do in Hillsdale?
Spend some time experiencing the great outdoors at Copake Lake and Mosquito Island. Discover sights such as Catamount Aerial Adventure Park, Catamount Ski Area, and Hillsdale Town Hall during your stay.
When is the best time to book a hotel with a pool in Hillsdale?
Taking into account the local weather in Hillsdale 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 68°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Hillsdale are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

Explore a world of travel with Expedia