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

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Check availability on Hillsdale Hotels with Swimming Pool

Tonight
18 Oct - 19 Oct
Tomorrow
19 Oct - 20 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
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 rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
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 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.
₹14,443
₹16,176 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 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.
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

2. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
₹23,421
₹29,343 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 hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
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.

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.
₹13,641
₹15,237 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 breakfast area with a counter, coffee machine, and a display of pastries.
A modern bathroom with a large mirror, a sink, and a shower.
A modern hotel lobby with seating areas, tables, and a reception desk.

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.
₹7,881
₹8,804 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 hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
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.
₹11,110
₹14,266 total
includes taxes & fees
20 Oct - 21 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A covered porch with wicker furniture and hanging flower baskets.
A bar with wooden floors and shelves filled with bottles.
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.
₹14,958
₹21,425 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
A large house with a balcony and a grassy yard.
A two-story building with a gabled roof and a chimney.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

7. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
₹9,828
₹10,978 total
includes taxes & fees
20 Oct - 21 Oct
The Little Lion
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

8. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
₹9,803
₹10,950 total
includes taxes & fees
21 Oct - 22 Oct
The Yankee Inn
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 restaurant with wooden flooring, bar area, and seating arrangements.
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

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.
₹11,928
₹13,323 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.
A modern bathroom with a white bathtub, a showerhead, and a towel rack.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.

10. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
  • Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
₹10,412
₹11,630 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Berkshires-Lenox
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"-"
Serena 1-night trip
Posted 7 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 8 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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