Find Hotels with a Pool in Sheffield, MA

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Check availability on Sheffield Hotels with a Pool

This weekend
May 29 - May 31
Next weekend
Jun 5 - Jun 7

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

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,010 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is ₩178,498
₩199,382 total
includes taxes & fees
May 30 - May 31
The Yankee Inn
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (956 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is ₩174,147
₩228,033 total
includes taxes & fees
May 31 - Jun 1
Berkshire Mountain Lodge
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (856 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is ₩118,498
₩132,361 total
includes taxes & fees
May 31 - Jun 1
Howard Johnson by Wyndham Lenox
Seasonal outdoor pool

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (183 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is ₩233,547
₩268,579 total
includes taxes & fees
Jun 1 - Jun 2
Blackberry River Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (562 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is ₩142,498
₩159,170 total
includes taxes & fees
Jun 11 - Jun 12
The Little Lion
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (413 reviews)
  • cleanliness
    Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
The price is ₩164,998
₩184,303 total
includes taxes & fees
May 31 - Jun 1
Sunset Inn
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (99 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is ₩202,497
₩226,189 total
includes taxes & fees
May 31 - Jun 1
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is ₩255,146
₩352,019 total
includes taxes & fees
Jun 22 - Jun 23
The Red Lion Inn
Indoor pool

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (678 reviews)
  • cleanliness
    Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
The price is ₩215,473
₩240,683 total
includes taxes & fees
Jun 4 - Jun 5
Hilton Garden Inn Lenox Pittsfield
Indoor pool

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (26 reviews)
  • cleanliness
    Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
The price is ₩266,996
₩298,234 total
includes taxes & fees
Jun 4 - Jun 5
Element by Marriott Lenox 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.
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Choose what matters most at hotels with a pool in Sheffield

Breakfast included
4 stars

Top Sheffield Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Everything was perfect!"
Mary 1-night trip
Posted 14 hours ago
Hampton Inn & Suites Berkshires-Lenox

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. Berkshire Mountain Lodge: Offers 3 restaurants, an outdoor pool, and spa services. Berkshires Untold: Features a seasonal outdoor pool, an indoor pool, and buffet. The Red Lion Inn: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. The Yankee Inn: Provides 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 Magnolia Bluffs Casino, Mount Everett State Reservation, 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.