TOP Hotels with Swimming Pool in Housatonic, MA for 2026

Q: What are some hotels with pools in Housatonic?

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. Quality Inn Great Barrington : Offers 3 restaurants, an outdoor pool and spa services. Berkshires Untold : Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. The Red Lion Inn : Hotel, 1-minute walk from Jiminy Peak Mountain Resort. Offers 2 hot tubs, an outdoor pool and 2 outdoor tennis courts.

A river flanked by autumn-colored trees and residential areas.

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Our top choices for Housatonic hotels with a pool

M3 Romantic Suite | Living area | 43-inch LCD TV with digital channels, streaming services

Blackberry River Inn

Norfolk

Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.

₹16,609 total

includes taxes & fees

11 Aug - 12 Aug

Breakfast, lunch, dinner and brunch served

The Old Inn On The Green

Great Barrington

Dive into summer luxury at this historic inn's outdoor pool surrounded by garden serenity and natural wonders.

₹38,454 total

includes taxes & fees

28 Jul - 29 Jul

Sunset Inn

Lee

Splash into a seasonal outdoor pool near Tanglewood Music Centre, offering a sunny retreat in a peaceful location.

₹11,052 total

includes taxes & fees

10 Aug - 11 Aug

Devonfield Inn B&B

Lee

Escape to an elegant countryside retreat with an inviting outdoor pool, premium spa services, and made-to-order gourmet breakfast.

₹44,117 total

includes taxes & fees

27 Aug - 28 Aug

2 indoor pools, 2 outdoor pools, pool umbrellas, pool loungers

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

South Lee

Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.

₹16,888 total

includes taxes & fees

25 Aug - 26 Aug

The Inn at Stockbridge

Stockbridge

Seasonal outdoor pool beckons for refreshing summer dips at this upscale bed and breakfast in Stockbridge.

₹41,997 total

includes taxes & fees

29 Jul - 30 Jul

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.

₹16,812 total

includes taxes & fees

23 Aug - 24 Aug

Hilton Garden Inn Lenox Pittsfield

Pittsfield

Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.

₹20,740 total

includes taxes & fees

9 Aug - 10 Aug

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Choose what matters most at hotels with a pool in Housatonic

Breakfast included

4 stars

Top Housatonic Hotel Reviews

Jiminy Peak Mountain Resort

10/10 Excellent

"Beautiful resort with great amenities, and friendly staff! My partner and I keep finding ourselves back here for a quick getaway! A great escape."

The Yankee Inn

8/10 Good

"Very clean lobby, breakfast area and our room. Comfortable bed and hotel was very accommodating in changing our initial room assignment based on my request for a first floor room. my husband has a disability. One constructive suggestion: air conditioning unit in our room was somewhat noisy though room was comfortably cool. Also housekeeping did not replace coffee mugs that we had used; they needed to be cleaned or swapped out for clean ones. Nice variety of breakfast foods and we had all that we needed. Fresh fruit was delicious appreciated. Overall we would definitely stay here again."

Frequently asked questions

What are some hotels with pools in Housatonic?

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. Quality Inn Great Barrington: Offers 3 restaurants, an outdoor pool and spa services. Berkshires Untold: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. The Red Lion Inn: Hotel, 1-minute walk from Jiminy Peak Mountain Resort. Offers 2 hot tubs, an outdoor pool and 2 outdoor tennis courts.

What is there to see and do in Housatonic?

Surround yourself with nature at Housatonic River. During your stay, visit sights such as Norman Rockwell Museum, Berkshire Botanical Garden and Naumkeag Museum.

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

Taking the local weather in Housatonic into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Housatonic are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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