The Best Hotels with a Pool in Hinsdale, MA from ₩132,759 in 2026

Q: What are some accommodations with pools in Hinsdale?

Berkshire Mountain Lodge : Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshires Untold : Provides a children's pool, an indoor pool, and free self parking. Vacation Village in the Berkshires : Features daily, an indoor pool, and free self parking. Hotel Downstreet, an Ascend Collection Hotel : Offers 3 restaurants, an outdoor pool, and spa services. The Red Lion Inn : Features a seasonal outdoor pool, an indoor pool, and buffet.

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Our top choices for Hinsdale 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.

₩233,584 total

includes taxes & fees

Jun 14 - Jun 15

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.

₩226,874 total

includes taxes & fees

Jun 4 - Jun 5

Berkshire Mountain Lodge

Pittsfield

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

₩238,016 total

includes taxes & fees

Jun 17 - Jun 18

The Red Lion Inn

Stockbridge

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

₩353,072 total

includes taxes & fees

Jun 9 - Jun 10

Cozy Corner Motel

Williamstown

Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.

₩149,755 total

includes taxes & fees

Jun 8 - Jun 9

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

Maple Terrace Motel

Williamstown

Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.

₩193,264 total

includes taxes & fees

Jun 8 - Jun 9

The Little Lion

Great Barrington

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

₩166,370 total

includes taxes & fees

Jun 2 - Jun 3

Howard Johnson by Wyndham Lenox

Lenox

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

₩132,759 total

includes taxes & fees

Jun 1 - Jun 2

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Choose what matters most at hotels with a pool in Hinsdale

Breakfast included

4 stars

Top Hinsdale Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good

"Pool and hot tub"

Vacation Village in the Berkshires

8/10 Good

"The place was nice quiet and peaceful. There is a few activities to do on site. Restaurants are not on the property or associated with them. My only issue was during check in. The lady kept sitting my cards on the counter instead of back in my hand like I handed them to here."

The Porches Inn at Mass MoCA

8/10 Good

"Loved my room, staff were friendly and helpful, and the breakfast included delicious bagels and lox. I hope to return, though I will specifically ask to not stay in the building that houses reception. It’s an historic building so not soundproofed, and I could hear every guest checking in and out, and all the sounds from the kitchen during breakfast hours - it was just a little noisy for me."

Frequently asked questions

What are some accommodations with pools in Hinsdale?

Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshires Untold: Provides a children's pool, an indoor pool, and free self parking. Vacation Village in the Berkshires: Features daily, an indoor pool, and free self parking. Hotel Downstreet, an Ascend Collection Hotel: Offers 3 restaurants, an outdoor pool, and spa services. The Red Lion Inn: Features a seasonal outdoor pool, an indoor pool, and buffet.

What is there to see and do in Hinsdale?

Make a point to visit attractions like Kennedy Park and Berkshire Museum. Discover sights such as Bas Ridge Golf Course during your stay.

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

Taking into account the local weather in Hinsdale is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Hinsdale are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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