Hotels with Swimming Pool, Hillsdale New York

Q: What are some accommodations with pools in Hillsdale?

The Yankee Inn : Features a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge : Offers free self parking, an indoor pool, and complimentary wireless internet access. The Red Lion Inn : Provides 3 restaurants, an outdoor pool, and spa services. Berkshires Untold : Offers buffet, an indoor pool, and complimentary wired internet access. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy : Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli.

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

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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, sun loungers

The Yankee Inn

Lenox

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

P8,747 total

includes taxes & fees

Jul 6 - Jul 7

Little Cat Lodge

Copake Falls

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

P10,487 total

includes taxes & fees

Jul 6 - Jul 7

Howard Johnson by Wyndham Saugerties

Saugerties

Swim in style at this Saugerties retreat with a year-round indoor pool and relaxing sauna for post-adventure recovery.

P8,619 total

includes taxes & fees

Jul 19 - Jul 20

The Red Lion Inn

Stockbridge

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

P15,239 total

includes taxes & fees

Jul 7 - Jul 8

Berkshire Inn

Pittsfield

Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.

P6,188 total

includes taxes & fees

Jul 6 - Jul 7

Berkshire Travel Lodge

Austerlitz

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

P4,654 total

includes taxes & fees

Jul 8 - Jul 9

The Little Lion

Great Barrington

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

P7,702 total

includes taxes & fees

Jul 5 - Jul 6

Berkshire Mountain Lodge

Pittsfield

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

P10,564 total

includes taxes & fees

Aug 2 - Aug 3

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Choose what matters most at hotels with a pool in Hillsdale

Breakfast included

4 stars

Top Hillsdale Hotel Reviews

Quality Inn Great Barrington

10/10 Excellent

"The rooms were clean and it is a good location for several restaurants. The staff was very friendly and helpful. When I realized there was no pool, the person at the desk told me of a pool about two miles away. We got a pass for our grandson and he had a great time."