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

Hotels with Swimming Pool in Hillsdale, New York

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Check availability on Hillsdale Hotels with Swimming Pool

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Hillsdale hotels with a pool

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
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.
A house with a stone patio and wooden stools.

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.
P10,658
P11,937 total
includes taxes & fees
Nov 1 - Nov 2
Little Cat Lodge
A poolside area with lounge chairs and a pool.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.
A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.

2. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
P23,402
P28,240 total
includes taxes & fees
Nov 1 - Nov 2
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 modern hotel lobby with a seating area, a sofa, and a large window with curtains.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

3. 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.
P10,066
P11,243 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
An indoor swimming pool with clear lane markings, a poolside area with lounge chairs, and large windows allowing natural light.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A modern bathroom with a large mirror, a sink, and a shower.
A breakfast area with a counter, coffee machine, and a display of pastries.

4. 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.
P6,328
P7,069 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Express Hotel & Suites Great Barrington by IHG
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A covered outdoor area with stone pillars and a view of a road and green hills.

5. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
  • Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness center.
P7,870
P8,791 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A bar with wooden floors and shelves filled with bottles.
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.

6. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
P9,925
P14,199 total
includes taxes & fees
Nov 1 - Nov 2
The Red Lion Inn
A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A building with a porch and multiple windows, surrounded by purple flowers.
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.
P7,331
P9,413 total
includes taxes & fees
Oct 18 - Oct 19
Holiday Inn Club Vacations Oak 'n Spruce Resort
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

8. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
P6,642
P7,419 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A large house with a balcony and a grassy yard.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.
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.

9. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
P6,485
P7,244 total
includes taxes & fees
Oct 18 - Oct 19
The Little Lion
A backyard with a swimming pool, a fenced area, and a view of the surrounding forest and hills.
A modern kitchen with white cabinetry, a wooden table, and a large window providing a view of the outdoors.
A spacious living area with a wooden ceiling, a brick fireplace, and a kitchen in the background.
A backyard with a hot tub, outdoor seating, and a patio area.

10. Charming 6 Bdrm Countryside Stay

Charming 6 Bdrm Countryside Stay
Great Barrington
P20,402
P54,117 total
includes taxes & fees
Oct 4 - Oct 5
Charming 6 Bdrm Countryside Stay
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

The Yankee Inn

The Yankee Inn

8/10 Good
"Room was nice but did not have the view I was hoping for. Another hotel property is mostly blocking views from Yankee Inn looking West; the direction rooms with balcony’s face. The location near"
Theresa 2-night trip
Posted 5 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."
Peter 1-night trip
Posted 3 days ago
Quality Inn Great Barrington

Frequently asked questions

What are some accommodations with pools in Hillsdale?
Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Quality Inn Great Barrington: Features a steam room, 3 indoor pools, and spa services. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Offers a seasonal outdoor pool, an indoor pool, and buffet. Pocketbook Hotel and Bath: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. The Yankee Inn: Provides 3 restaurants, an outdoor pool, and spa services.
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.

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