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

Hillsdale Hotel with Pool

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Check availability on Hillsdale Hotel with Pool

Tonight
19 Oct - 20 Oct
Tomorrow
20 Oct - 21 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Hillsdale hotels with a pool

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.
A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

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.
HK$1,194
HK$1,337 total
includes taxes & fees
2 Nov - 3 Nov
Little Cat Lodge
A poolside area with lounge chairs and a pool.
A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

2. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
HK$2,225
HK$2,748 total
includes taxes & fees
9 Nov - 10 Nov
Prospect Berkshires
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
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.
HK$1,127
HK$1,259 total
includes taxes & fees
2 Nov - 3 Nov
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 modern bathroom with a large mirror, a sink, and a shower.
A modern hotel lobby with seating areas, tables, and a reception desk.
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.
HK$651
HK$728 total
includes taxes & fees
17 Nov - 18 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A building with a porch and multiple windows, surrounded by purple flowers.
A living room with a sofa, armchair, coffee table, and a patterned rug.

5. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
HK$918
HK$1,179 total
includes taxes & fees
26 Oct - 27 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
An indoor swimming pool with a concrete floor, a large window, and a vase with flowers.
A spacious bedroom with a large bed, a wooden headboard, a bedside table with a book and a glass, and a window with curtains.
A restaurant with long tables, chairs, and a brick wall.
A spacious room with leather seating, large windows, and exposed brick walls.

6. Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
Hudson
HK$1,836
HK$2,430 total
includes taxes & fees
15 Nov - 16 Nov
Pocketbook Hotel and Bath
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A covered porch with wicker furniture and hanging flower baskets.
A bar with wooden floors and shelves filled with bottles.

7. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
HK$1,236
HK$1,771 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
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 sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.
A two-story building with a gabled roof and a chimney.

8. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
HK$812
HK$907 total
includes taxes & fees
20 Oct - 21 Oct
The Little Lion
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
A covered outdoor area with stone pillars and a view of a road and green hills.

9. 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 centre.
HK$986
HK$1,101 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
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.

10. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
HK$832
HK$929 total
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
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Choose what matters most at hotels with a pool in Hillsdale

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Hillsdale Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"-"
Serena 1-night trip
Posted 16 hours ago
Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

8/10 Good
"Lovely, super clean unit with nice furnishings, however, the dining chair cushions need a good cleaning as the dirt could be seen. There also was candy/gum stuck to one of the cushions and another cushion was completely loose from the chair. There was mention of a "two-burner hotplate" in the description, but the photos showed a two-burner electric stove top. What actually is there is a two-burner infared hotplate. Instructions on how to use it is posted on the wall above the sink, not on the wall above the hotplate. Unfortunately, we were assigned an end unit in Building #13, which is currently being renovated. There was a family occupying the unit above us. The children ran up and down the stair and allowed the outside door to slam each and every time until late in the evening. No noise during quiet hours though. :o)"
Julio 1-night trip
Posted 17 hours ago
The Yankee Inn

Frequently asked questions

What are some accommodation options 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 swimming 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 swimming pools, 2 outdoor swimming 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 the local weather in Hillsdale into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillsdale are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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