Book the Best Hotels with POOL in Hillsdale in 2026 | Expedia.ca

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

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

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Check availability on Hillsdale Hotels with a Pool

Tonight

Jun 16 - Jun 17

Tomorrow

Jun 17 - Jun 18

This weekend

Jun 19 - Jun 21

Next weekend

Jun 26 - Jun 28

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.

CA $174 total

includes taxes & fees

Jun 21 - Jun 22

Exterior

The Little Lion

Great Barrington

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

CA $138 total

includes taxes & fees

Jun 18 - Jun 19

Exterior

Howard Johnson by Wyndham Lenox

Lenox

Summertime splashes await at this refreshing outdoor pool oasis in Lenox.

CA $139 total

includes taxes & fees

Jun 22 - Jun 23

Outdoor pool

Berkshire Travel Lodge

Austerlitz

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

CA $103 total

includes taxes & fees

Jun 18 - Jun 19

Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

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

CA $219 total

includes taxes & fees

Jun 22 - Jun 23

Indoor pool

Berkshire Mountain Lodge

Pittsfield

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

CA $251 total

includes taxes & fees

Jul 16 - Jul 17

Seasonal outdoor pool

Little Cat Lodge

Copake Falls

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

CA $238 total

includes taxes & fees

Jun 29 - Jun 30

Outdoor pool, sun loungers

The Red Lion Inn

Stockbridge

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

CA $305 total

includes taxes & fees

Jul 1 - Jul 2

View all properties

Choose what matters most at hotels with a pool in Hillsdale

Breakfast included

4 stars

Top Hillsdale Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent

"Can not say enough about our stay at The Yankee. Loved it!!!!! Updated, clean, incredibly freindly staff..... we will definitely be back."

The Red Lion Inn

The Red Lion Inn

10/10 Excellent

"The Red Lion Inn has so much history and character, it was a wonderful Experience to say the least. With modern amenities, it still Managed to keep its old world charm Food at the Wolf Den Tavern offered some of the best clam chowder I have ever had Enjoyed the hot tub but both hot tub and pool were difficult getting in and out of for someone with mobility issues like me Breakfast in the main dining room was also wonderful with very pleasant staff Upon check in, the only employee at the registration desk was on the phone with a customer for a good 15-20 minutes while the line behind me were all waiting to check in. Since check in time is 4:00, and we were there at 4:30 it seems like there should be more than one employee checking in customers Overall a wonderful stay. One that I would happily do again"

Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie

10/10 Excellent

"There was nothing I can complain about the room beautiful clean very comfortable very relaxing. I might add wonderful. They took care of me right away gave me a first floor and accommodated me and helped me with another problem. I needed to get closer to my venue where the wedding was help. It’s very helpful thank you so much."

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. The Yankee Inn: Offers a seasonal outdoor pool, an indoor pool, and buffet. Quality Inn Great Barrington: Hotel, 15-minute walk from National Shrine of the Divine Mercy. Features 3 restaurants, an outdoor pool, and spa services. Berkshires Untold: Hotel located near National Shrine of the Divine Mercy. Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Features buffet, an indoor pool, and complimentary wired internet access.

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.

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