TOP Hotels with Pool in Sheffield, MA for 2026

Q: What are some accommodation options 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 high-speed (wired) Internet access. The Red Lion Inn : Provides 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli.

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Sheffield Hotels with Pool

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Sheffield hotels with a pool

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

The Yankee Inn

Lenox

Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.

฿5,623 total

includes taxes & fees

13 Jul - 14 Jul

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.

฿7,871 total

includes taxes & fees

20 Jul - 21 Jul

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.

฿5,171 total

includes taxes & fees

26 Jul - 27 Jul

Interlaken Inn & Resort

Lakeville

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

฿9,269 total

includes taxes & fees

19 Jul - 20 Jul

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.

฿5,961 total

includes taxes & fees

14 Jul - 15 Jul

Little Cat Lodge

Copake Falls

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

฿8,222 total

includes taxes & fees

23 Jul - 24 Jul

Berkshire Travel Lodge

Austerlitz

Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.

฿2,517 total

includes taxes & fees

14 Jul - 15 Jul

Hilton Garden Inn Lenox Pittsfield

Pittsfield

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

฿7,835 total

includes taxes & fees

19 Jul - 20 Jul

View all properties

Choose what matters most at hotels with a pool in Sheffield

Breakfast included

4 stars

Top Sheffield Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"I found the staff very helpful, especially the young man who worked over night. We experienced a slight problem, and he could not have been nicer. He represented the hotel extremely well. Breakfast was uninspiring but generally good. The view from the breakfast room is lovely. The common areas seem a little tired, but the room was very good value - especially as we overlooked the lake. The location is wonderful for Lee, Lenox, Stockbridge, all the cultural centers and the Mass Pike. A beach is adjacent for swimming. We plan to return next year."

Frequently asked questions

What are some accommodation options 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 high-speed (wired) Internet access. The Red Lion Inn: Provides 2 indoor swimming pools, 2 outdoor swimming 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 the local weather in Sheffield into account can help you maximise your time at the pool during your trip. 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 -2°C. The snowiest months in Sheffield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

Explore a world of travel with Expedia

More ways to book

Book Hotels with Pool in Sheffield on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Sheffield Hotels with Pool