The Best Hotels with a Pool in Sheffield, MA from AED 406 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 : Offers 3 restaurants, an outdoor pool, and spa services. Berkshires Untold : Features buffet, an indoor pool, and complimentary wired internet access. The Red Lion Inn : Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli.

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Our top choices for Sheffield hotels with a pool

Blackberry River Inn

Norfolk

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

AED 605 total

includes taxes & fees

13 Jul - 14 Jul

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.

AED 1,463 total

includes taxes & fees

13 Jul - 14 Jul

Sunset Inn

Lee

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

AED 451 total

includes taxes & fees

13 Jul - 14 Jul

Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

Cornwall Inn and Lodge

Cornwall Bridge

Serene seasonal outdoor pool retreat nestled near Mohawk Mountain, where pool loungers and umbrellas invite summer relaxation.

AED 918 total

includes taxes & fees

12 Jul - 13 Jul

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.

AED 1,801 total

includes taxes & fees

21 Jul - 22 Jul

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.

AED 715 total

includes taxes & fees

29 Jul - 30 Jul

The Inn at Stockbridge

Stockbridge

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

AED 1,649 total

includes taxes & fees

20 Jul - 21 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.

AED 624 total

includes taxes & fees

16 Jul - 17 Jul

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Choose what matters most at hotels with a pool in Sheffield

Breakfast included

4 stars

Top Sheffield Hotel Reviews

The Yankee Inn

8/10 Good

"The hotel is a few minutes from Tanglewood and the Berkshire hotspots. Super friendly staff. Very accommodating. The place is a bit dated, but that has a retro charm like places on the Cape. The grounds are lovely. The breakfast is like other hotel breakfast. Lots of options: cereal, oatmeal, eggs, sausage, hard boiled eggs, fruit, bread, pastries, etc. My only complaint was the bed, which had a mattress in desperate need of replacement. We referred to it as sleeping in the valley because it made us roll to the center. It was also really high, which was challenging in an accessible room. I called and they had a stool for me within 5 minutes so we made it work. The people were so nice so I hate adding a complaint in my review. We would have asked for a room change but were there over a holiday weekend and I was pretty sure there wouldn’t be another option. The pluses outweigh the negatives so we had a good time."

The Red Lion Inn

10/10 Excellent

"Had a lovely 2 night stay at the Red Lion Inn. The front desk staff were very welcoming. The location was convenient to many nice shops and restaurants, as well as sites like the Norman Rockwell museum and the Divine Mercies chapel and grounds. This hotel is a wonderful blend of historic and modern..and the breakfast is great!"

Holiday Inn Express Hotel & Suites Great Barrington by IHG

8/10 Good

"A sweet spot in the Berkshires to “camp” in for an evening or two or three. Who else has your bed made up with crisp white sheets, breakfast in the morning and a warm welcome waiting for you other than your mom? #holidayinnexpress for the win! Thanks!"

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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: Offers 3 restaurants, an outdoor pool, and spa services. Berkshires Untold: Features buffet, an indoor pool, and complimentary wired internet access. The Red Lion Inn: Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli.

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, Bartholomew's Cobble, and Mount Everett State Reservation 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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