Hotels with Swimming Pool in Sheffield, Massachusetts

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Our top choices for Sheffield hotels with a pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (895 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is P5,218
P7,174 total
includes taxes & fees
May 6 - May 7
Berkshire Mountain Lodge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
  • cleanliness
    Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
The price is P8,613
P9,621 total
includes taxes & fees
Apr 13 - Apr 14
Element Lenox Berkshires

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (555 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is P6,626
P7,401 total
includes taxes & fees
Apr 8 - Apr 9
The Little Lion

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (754 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is P6,927
P7,738 total
includes taxes & fees
Apr 20 - Apr 21
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (844 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is P4,758
P5,315 total
includes taxes & fees
Apr 7 - Apr 8
Howard Johnson by Wyndham Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is P7,180
P8,020 total
includes taxes & fees
Apr 20 - Apr 21
Hampton Inn & Suites Berkshires-Lenox

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (173 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is P9,378
P10,785 total
includes taxes & fees
Apr 12 - Apr 13
Blackberry River Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is P8,077
P11,714 total
includes taxes & fees
Apr 30 - May 1
The Red Lion Inn

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
  • cleanliness
    Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
The price is P5,722
P6,392 total
includes taxes & fees
Apr 7 - Apr 8
Sunset Inn

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (75 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
The price is P9,162
P10,261 total
includes taxes & fees
Apr 7 - Apr 8
Little Cat Lodge
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.

Choose what matters most at hotels with a pool in Sheffield

Top Sheffield Hotel Reviews

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: Hotel located near National Shrine of the Divine Mercy. Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Berkshires Untold: Features a seasonal outdoor pool, an indoor pool, and buffet. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Hotel, 15-minute walk from National Shrine of the Divine Mercy. Provides 3 restaurants, an outdoor pool, and spa services. The Yankee, Trademark Collection by Wyndham: Hotel located near Tanglewood Music Center. Features a snack bar/deli, an indoor pool, and free self parking.
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, Ashley House, 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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