The Best Hotels with a Pool in Spencertown, NY from ₩111,339 in 2026

Q: What are some accommodations with pools in Spencertown?

Berkshire Mountain Lodge : Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshires Untold : Provides a seasonal outdoor pool, an indoor pool, and buffet. The Yankee Inn : Offers 3 restaurants, an outdoor pool, and spa services. Quality Inn Great Barrington : Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli. The Red Lion Inn : Provides buffet, an indoor pool, and complimentary wired internet access.

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Our top choices for Spencertown 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.

₩223,101 total

includes taxes & fees

Jul 1 - Jul 2

The Little Lion

Great Barrington

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

₩148,738 total

includes taxes & fees

Jun 14 - Jun 15

The Red Lion Inn

Stockbridge

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

₩324,206 total

includes taxes & fees

Jun 16 - Jun 17

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.

₩223,817 total

includes taxes & fees

Jun 7 - Jun 8

Howard Johnson by Wyndham Lenox

Lenox

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

₩133,527 total

includes taxes & fees

Jun 15 - Jun 16

Berkshire Mountain Lodge

Pittsfield

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

₩240,160 total

includes taxes & fees

Jun 24 - Jun 25

Berkshire Inn

Pittsfield

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

₩145,339 total

includes taxes & fees

Jun 10 - Jun 11

Berkshire Travel Lodge

Austerlitz

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

₩111,339 total

includes taxes & fees

Jun 5 - Jun 6

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Choose what matters most at hotels with a pool in Spencertown

Breakfast included

4 stars

Top Spencertown Hotel Reviews

Spark by Hilton West Coxsackie

10/10 Excellent

"The bedding was gross but everything else was good"

Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"I enjoyed relaxing by the firepit. The only thing that could of made it a better stay would be free breakfast or at least coffee and tea. They have a Starbucks and area where you can purchase items but it was more like self serve and pay at reception desk."

Holiday Inn & Suites Pittsfield-Berkshires by IHG

6/10 Okay

"The staff were very polite and helpful. But the property was under construction, so you had to walk over a block to your car and park it or you can do a valet that was never present? From what I was told from other people that were staying there is that the place I’ve been under construction for a couple years now that was not advertise that was going on so it was kind of frustrating."

Frequently asked questions

What are some accommodations with pools in Spencertown?

Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshires Untold: Provides a seasonal outdoor pool, an indoor pool, and buffet. The Yankee Inn: Offers 3 restaurants, an outdoor pool, and spa services. Quality Inn Great Barrington: Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli. The Red Lion Inn: Provides buffet, an indoor pool, and complimentary wired internet access.

What is there to see and do in Spencertown?

Make a point to visit attractions like Queechy Lake and Berkshire Botanical Garden. During your stay, check out sights such as The Mac-Haydn Theatre, Norman Rockwell Museum, and Catamount Aerial Adventure Park.

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

Taking into account the local weather in Spencertown 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 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Spencertown are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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