Book the Best Hotels with POOL in Hillsdale in 2026

Q: 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.

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Our top choices for Hillsdale hotels with a pool

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

1. Little Cat Lodge

Copake Falls

Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.

CA $233 total

includes taxes & fees

Dec 9 - Dec 10

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

2. 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.

CA $131 total

includes taxes & fees

Dec 7 - Dec 8

A poolside area with white lounge chairs and a red umbrella.

3. Prospect Berkshires

Egremont

Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.

CA $424 total

includes taxes & fees

Nov 30 - Dec 1

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

4. 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.

CA $254 total

includes taxes & fees

Nov 12 - Nov 13

A large house with a balcony and a grassy yard.

5. The Little Lion

Great Barrington

Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.

CA $161 total

includes taxes & fees

Nov 9 - Nov 10

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

6. The Red Lion Inn

Stockbridge

Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.

CA $319 total

includes taxes & fees

Nov 17 - Nov 18

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

7. The Yankee Inn

Lenox

Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.

CA $173 total

includes taxes & fees

Dec 9 - Dec 10

An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.

8. 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.

CA $212 total

includes taxes & fees

Nov 11 - Nov 12

An indoor swimming pool with a concrete floor, a large window, and a vase with flowers.

9. Pocketbook Hotel and Bath

Hudson

CA $399 total

includes taxes & fees

Dec 1 - Dec 2

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

10. Berkshire Mountain Lodge

Pittsfield

Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.

CA $153 total

includes taxes & fees

Dec 6 - Dec 7

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Choose what matters most at hotels with a pool in Hillsdale

Breakfast included

4 stars

Top Hillsdale Hotel Reviews

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

10/10 Excellent

Kelly

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

South Lee

10/10 Excellent

Andrea

The Little Lion

Great Barrington

10/10 Excellent

Janice

Hampton Inn & Suites Berkshires-Lenox

Lenox

10/10 Excellent

Smadar

A large, two-story house with a well-maintained lawn and a fence.

Devonfield Inn B&B

Lee

10/10 Excellent

We stayed at the Devonfield Inn in mid-October during peak foliage season. The hotel is a wonderful historic home built in 1800 with much of its historic character preserved. Our hosts were so welcoming and made us feel at home. The room was very comfortable and breakfast was fantastic. In the morning, we got a special surprise to see a bear on the patio drinking from the fountain and robbing the bird feeder. Overall we highly recommend the Devonfield. We will definitely go back.

Lise

A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

10/10 Excellent

Anonymous traveller

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.

Find Hotels with a Pool in Hillsdale, NY from CA $108

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Treat yourself

Be picky

Check prices for these dates

Our top choices for Hillsdale hotels with a pool

1. Little Cat Lodge

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

3. Prospect Berkshires

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

5. The Little Lion

6. The Red Lion Inn

7. The Yankee Inn

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

9. Pocketbook Hotel and Bath

10. Berkshire Mountain Lodge

Choose what matters most at hotels with a pool in Hillsdale

Top Hillsdale Hotel Reviews

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

Frequently Asked Questions

What are some accommodations with pools in Hillsdale?

What is there to see and do in Hillsdale?

When is the best time to book a hotel with a pool in Hillsdale?

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