The Best Hotels with a Pool in Sheffield, MA from NT$4,060 in 2026

Q: What are some accommodations with pools in Sheffield?

Wilder House Berkshires : Offers free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge : Provides a seasonal outdoor pool, an indoor pool, and buffet. The Yankee Inn : Features 3 restaurants, an outdoor pool, and spa services. Berkshires Untold : Offers buffet, an indoor pool, and complimentary wired internet access. Quality Inn Great Barrington : Features free self parking, an outdoor pool, and flat-screen televisions.

A covered wooden structure with a sloped roof, surrounded by greenery and trees.

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Our top choices for Sheffield hotels with a pool

1. 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.

NT$7,024 total

includes taxes & fees

Aug 17 - Aug 18

2. 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.

NT$5,629 total

includes taxes & fees

Aug 30 - Aug 31

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

3. Blackberry River Inn

Norfolk

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

NT$7,059 total

includes taxes & fees

Aug 11 - Aug 12

4. Little Cat Lodge

Copake Falls

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

NT$7,978 total

includes taxes & fees

Aug 23 - Aug 24

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

5. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

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

NT$5,471 total

includes taxes & fees

Aug 31 - Sep 1

6. The Little Lion

Great Barrington

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

NT$4,060 total

includes taxes & fees

Sep 1 - Sep 2

7. The Red Lion Inn

Stockbridge

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

NT$8,068 total

includes taxes & fees

Aug 23 - Aug 24

8. Interlaken Inn & Resort

Lakeville

Immerse in the sun-drenched seasonal outdoor pool surrounded by lush resort grounds and full-service spa amenities.

NT$9,998 total

includes taxes & fees

Aug 17 - Aug 18

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Choose what matters most at hotels with a pool in Sheffield

Breakfast included

4 stars

Top Sheffield Hotel Reviews

Howard Johnson by Wyndham Lenox

10/10 Excellent

"Parking"

Quality Inn Great Barrington

8/10 Good

"The motel was clean (rooms and outdoor) and Brian at the reception was kind and helpful. It is also convenietnly located next to a CVS and 2 minutes walk from downtown Great Barrington. The place and the rooms are very basic, which makes me wonder what brings the price we paid to be so high. We have not tried the breakfast."

Frequently asked questions

What are some accommodations with pools in Sheffield?

Wilder House Berkshires: Offers free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Provides a seasonal outdoor pool, an indoor pool, and buffet. The Yankee Inn: Features 3 restaurants, an outdoor pool, and spa services. Berkshires Untold: Offers buffet, an indoor pool, and complimentary wired internet access. Quality Inn Great Barrington: Features free self parking, an outdoor pool, and flat-screen televisions.

What is there to see and do in Sheffield?

Spend some time experiencing the great outdoors at Housatonic River. Discover sights such as Magnolia Bluffs Casino, Suter Farm, and Thom Reed UFO Monument Park during your stay.

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

Taking into account the local weather in Sheffield 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 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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Check availability on Sheffield Hotels with a Pool

Our top choices for Sheffield hotels with a pool

1. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires