TOP Hotels with Swimming Pool in Hillsdale, NY for 2026

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

The Yankee Inn : Offers a seasonal outdoor pool, an indoor pool and buffet. Quality Inn Great Barrington : Features free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge : Features 3 restaurants, an outdoor pool and spa services. Berkshires Untold : Provides buffet, an indoor pool and complimentary high-speed (wired) Internet access. The Red Lion Inn : Features a steam room, 3 indoor swimming pools and spa services.

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

Little Cat Lodge

Copake Falls

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

₹23,820 total

includes taxes & fees

4 Aug - 5 Aug

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.

₹15,283 total

includes taxes & fees

13 Aug - 14 Aug

The Little Lion

Great Barrington

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

₹13,551 total

includes taxes & fees

11 Aug - 12 Aug

Berkshire Travel Lodge

Austerlitz

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

₹7,278 total

includes taxes & fees

2 Aug - 3 Aug

Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, pool loungers

Prospect Berkshires

Egremont

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

₹48,319 total

includes taxes & fees

19 Aug - 20 Aug

The Red Lion Inn

Stockbridge

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

₹23,217 total

includes taxes & fees

29 Jul - 30 Jul

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.

₹20,971 total

includes taxes & fees

13 Aug - 14 Aug

Deep-tissue massages, Swedish massages, facials, 5 treatment rooms

Pocketbook Hotel and Bath

Hudson

₹26,002 total

includes taxes & fees

20 Aug - 21 Aug

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Choose what matters most at hotels with a pool in Hillsdale

Breakfast included

4 stars

Top Hillsdale Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"As of late we have been traveling with our small dog. Most hotels that accept pets you end up in the most dinghy room and not kept well. Not here the room was clean well kept and no odor. "

The Yankee Inn

10/10 Excellent

"The room was neat and had access to outside to enjoy sitting. The fridge in the room was a convenient size for cold and frozen foods. The staff was responsive to issues, even when I told them they could wait to fix it until after we left (it was fixed quickly. The breakfast was excellent and offered a nice variety. Would happily stay here again."

The Red Lion Inn

8/10 Good

"Dinner in the main dining room was amazing! Food delicious and staff attentive. We stayed in the Stephen’s House and arrived in the dark. It was not well lighted and 184 was up a huge flight of stairs. We had to haul up too many bags! We would have done a sm. 1 night bag If we had known this was a second floor. Beds were very uncomfortable soft and towels with stains. The kitchen area was without a refrigerator turned on and no ice. The front desk attendant was very efficient and ran some ice over! We love Red Lion Inn and found some things a bit off this time."

Frequently asked questions

What are some accommodation options with pools in Hillsdale?

The Yankee Inn: Offers a seasonal outdoor pool, an indoor pool and buffet. Quality Inn Great Barrington: Features free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Features 3 restaurants, an outdoor pool and spa services. Berkshires Untold: Provides buffet, an indoor pool and complimentary high-speed (wired) Internet access. The Red Lion Inn: 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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