A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

Find Hotels with a Pool in Sheffield, MA from CA $129

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Check availability on Sheffield Hotels with a Pool

This weekend
Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

Our top choices for Sheffield hotels with a pool

Interior detail

1. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
United States
Liliana
The price is CA $229
CA $256 total
includes taxes & fees
Nov 12 - Nov 13
Wilder House Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at hotels with a pool in Sheffield

Breakfast included
4 stars

Top Sheffield Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Office staff wonderful! Room clean but older carpet and bathroom looked dingy."
Martha 1-night trip
Posted 17 hours ago
Quality Inn Great Barrington

Frequently asked questions

What are some accommodations with pools in Sheffield?
Wilder House Berkshires: Provides free self parking, an indoor pool, and complimentary wireless internet access. Antique Farmhouse Totally Restored: Offers a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge: Offers 3 restaurants, an outdoor pool, and spa services. Quality Inn Great Barrington: Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli. The Yankee Inn: Features buffet, an indoor pool, and complimentary wired internet access.
What is there to see and do in Sheffield?
Spend some time experiencing the great outdoors at Housatonic River. Discover sights such as Suter Farm, Ashley House, 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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