Sheffield Hotel Guide - Hotels with Pool in Sheffield, Massachusetts

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Check availability on Sheffield Hotels with Pool

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

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

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 €133
includes taxes & fees
15 Jun - 16 Jun
The Yankee Inn
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (955 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is €131
includes taxes & fees
31 May - 1 Jun
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 €76
includes taxes & fees
31 May - 1 Jun
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 €154
includes taxes & fees
31 May - 1 Jun
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 €91
includes taxes & fees
11 Jun - 12 Jun
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 Centre, offering a sunny retreat in a peaceful location.
The price is €106
includes taxes & fees
31 May - 1 Jun
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 €130
includes taxes & fees
31 May - 1 Jun
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 €202
includes taxes & fees
4 Jun - 5 Jun
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 €138
includes taxes & fees
4 Jun - 5 Jun
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 €175
includes taxes & fees
3 Jun - 4 Jun
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 7 hours ago
Hampton Inn & Suites Berkshires-Lenox

Frequently asked questions

What are some accommodation options with pools in Sheffield?
Wilder House Berkshires: Provides free self parking, an indoor pool and complimentary wireless Internet access. Luxury Private Estate in the Berkshires | Whitney by AvantStay: Offers 3 restaurants, an outdoor pool and spa services. Berkshire Mountain Lodge: Features a seasonal outdoor pool, an indoor pool and buffet. Berkshires Untold: Offers 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. The Red Lion Inn: Provides buffet, an indoor pool and complimentary high-speed (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 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.