FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

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Check availability on Sheffield Hotels with a Pool

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, (1,015 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is ￥17,827
￥19,913 total
includes taxes & fees
Jun 17 - Jun 18
The Yankee Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (567 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is ￥14,108
￥15,758 total
includes taxes & fees
Jun 18 - Jun 19
The Little Lion
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (867 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is ￥14,268
￥15,937 total
includes taxes & fees
Jun 17 - Jun 18
Howard Johnson by Wyndham Lenox
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (107 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is ￥22,445
￥25,071 total
includes taxes & fees
Jun 22 - Jun 23
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (980 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is ￥19,500
￥25,363 total
includes taxes & fees
Jun 24 - Jun 25
Berkshire Mountain Lodge
Outdoor pool, sun loungers

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,010 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is ￥23,887
￥33,845 total
includes taxes & fees
Jul 1 - Jul 2
The Red Lion Inn
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (469 reviews)
  • cleanliness
    Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
The price is ￥10,531
￥11,796 total
includes taxes & fees
Jun 17 - Jun 18
Berkshire Travel Lodge
M3 Romantic Suite | Living area | 43-inch LCD TV with digital channels, streaming services

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (186 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is ￥23,827
￥27,401 total
includes taxes & fees
Jun 23 - Jun 24
Blackberry River Inn
Seasonal outdoor pool

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (81 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
The price is ￥24,385
￥27,313 total
includes taxes & fees
Jun 23 - Jun 24
Little Cat Lodge
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is ￥22,958
￥25,644 total
includes taxes & fees
Jun 21 - Jun 22
Hampton Inn & Suites Berkshires-Lenox
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Can not say enough about our stay at The Yankee. Loved it!!!!! Updated, clean, incredibly freindly staff..... we will definitely be back."
Marie 1-night trip
Posted 6 hours ago
The Yankee Inn

Frequently asked questions

What are some accommodations with pools in Sheffield?
Wilder House Berkshires: Features free self parking, an indoor pool, and complimentary wireless internet access. Luxury Private Estate in the Berkshires | Whitney by AvantStay: Features a seasonal outdoor pool, an indoor pool, and buffet. Antique Farmhouse Totally Restored: Provides 3 restaurants, an outdoor pool, and spa services. Berkshire Mountain Lodge: Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Berkshires Untold: Features 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, Thom Reed UFO Monument Park, and Lime Kiln Farm Wildlife Sanctuary 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.