Hillsdale Hotels with Pool, New York: Hillsdale Hotel Guide

Q: What are some accommodation options with pools in Hillsdale?

Berkshire Mountain Lodge : Features free self parking, an indoor pool and complimentary wireless Internet access. Berkshires Untold : Features 3 restaurants, an outdoor pool and spa services. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy : Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. The Red Lion Inn : Features 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. Hampton Inn & Suites Berkshires-Lenox : Features a steam room, 3 indoor swimming pools and spa services.

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Our top choices for Hillsdale hotels with a pool

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

The Yankee Inn

Lenox

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

Emma

includes taxes & fees

29 May - 30 May

Berkshire Mountain Lodge

Pittsfield

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

Danielle

includes taxes & fees

31 May - 1 Jun

The Little Lion

Great Barrington

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

Lisa

includes taxes & fees

11 Jun - 12 Jun

Berkshire Travel Lodge

Austerlitz

Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.

Alexandra

includes taxes & fees

4 Jun - 5 Jun

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Pittsfield

Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.

Camille

includes taxes & fees

1 Jun - 2 Jun

The Red Lion Inn

Stockbridge

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

Judith Pauline

includes taxes & fees

4 Jun - 5 Jun

Blackberry River Inn

Norfolk

Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.

Diane

includes taxes & fees

28 May - 29 May

Little Cat Lodge

Copake Falls

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

Evelyn

includes taxes & fees

4 Jun - 5 Jun

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Choose what matters most at hotels with a pool in Hillsdale

Breakfast included

4 stars

Top Hillsdale Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"Room was clean. Bed was comfortable. Pool was nice. Bar was great."

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"Great location close to everything. The staff was very helpful. The breakfast was perfect in every way. The room was also perfect… nice little kitchen… No dishes or silverware but I sink and refrigerator microwave , coffee pot so just enough. Really comfortable bed!"

The Red Lion Inn

10/10 Excellent

"Every year my sisters and I go to the Red Lion to celebrate our mom’s birthday. It was one of her favorite places! We love the charm, the history and the “old fashioned” feel. Every guest room is different and they kindly upgraded me to a suite the last two times. The food at the restaurant is really good and we always love hearing the Jazz in the Lion’s Den on Sunday night. Can’t wait to return next year."

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. Berkshires Untold: Features 3 restaurants, an outdoor pool and spa services. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. The Red Lion Inn: Features 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. Hampton Inn & Suites Berkshires-Lenox: Features a steam room, 3 indoor swimming pools 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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