Hotels with Swimming Pool, Sheffield Massachusetts

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.

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 Swimming Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Sheffield hotels with a pool

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

The Yankee Inn

Lenox

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

P8,728 total

includes taxes & fees

Jul 7 - Jul 8

The Red Lion Inn

Stockbridge

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

P14,217 total

includes taxes & fees

Jul 7 - Jul 8

Hilton Garden Inn Lenox Pittsfield

Pittsfield

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

P12,958 total

includes taxes & fees

Jul 8 - Jul 9

Interlaken Inn & Resort

Lakeville

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

P17,102 total

includes taxes & fees

Jul 19 - Jul 20

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.

P11,322 total

includes taxes & fees

Jul 27 - Jul 28

Howard Johnson by Wyndham Lenox

Lenox

Summertime splashes await at this refreshing outdoor pool oasis in Lenox.

P6,793 total

includes taxes & fees

Jul 7 - Jul 8

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.

P13,939 total

includes taxes & fees

Jul 19 - Jul 20

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.

P11,363 total

includes taxes & fees

Jul 12 - Jul 13

View all properties

Choose what matters most at hotels with a pool in Sheffield

Breakfast included

4 stars

Top Sheffield Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"Clean"

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!"

The Red Lion Inn

10/10 Excellent

"Staff was very helpful particularly Jerry in outside cafe. Grounds keeper did a beautiful job! Outdoor pool was amazing! Will be back to swim in in the winter. Loved the shops located in the main building. We stayed in Maple Glen which was lovely. I was disappointed my room was dark but now know to ask for a sunnier room when booking."

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.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Sheffield Hotels with Swimming Pool