The Best Hotels with a Pool in Sheffield, MA from NT$3,575 in 2026

Q: What are some accommodations with pools in Sheffield?

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

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

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$5,494 total

includes taxes & fees

Aug 16 - Aug 17

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.

NT$5,789 total

includes taxes & fees

Jul 21 - Jul 22

The Little Lion

Great Barrington

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

NT$4,550 total

includes taxes & fees

Jul 22 - Jul 23

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$8,270 total

includes taxes & fees

Aug 10 - Aug 11

Little Cat Lodge

Copake Falls

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

NT$7,984 total

includes taxes & fees

Aug 19 - Aug 20

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

NT$7,205 total

includes taxes & fees

Jul 29 - Jul 30

The Red Lion Inn

Stockbridge

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

NT$8,140 total

includes taxes & fees

Jul 29 - Jul 30

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.

NT$12,438 total

includes taxes & fees

Jul 21 - Jul 22

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Choose what matters most at hotels with a pool in Sheffield

Breakfast included

4 stars

Top Sheffield Hotel Reviews

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 accommodations with pools in Sheffield?

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

What is there to see and do in Sheffield?

Surround yourself with nature at Housatonic River and Bartholomews Cobble. Discover sights such as Magnolia Bluffs Casino, Bartholomew's Cobble, 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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Our top choices for Sheffield hotels with a pool