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

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Check availability on Sheffield Hotels with Pool

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, (1,011 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is ฿3,653
฿4,080 total
includes taxes & fees
10 Jun - 11 Jun
The Yankee Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (563 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is ฿2,891
฿3,229 total
includes taxes & fees
11 Jun - 12 Jun
The Little Lion
Outdoor pool, pool loungers

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,005 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is ฿5,177
฿7,251 total
includes taxes & fees
22 Jun - 23 Jun
The Red Lion Inn
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, (102 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is ฿4,435
฿4,954 total
includes taxes & fees
14 Jun - 15 Jun
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (864 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is ฿2,595
฿2,899 total
includes taxes & fees
10 Jun - 11 Jun
Howard Johnson by Wyndham Lenox
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (971 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is ฿4,169
฿5,391 total
includes taxes & fees
9 Jul - 10 Jul
Berkshire Mountain Lodge
Seasonal outdoor pool

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 ฿5,115
฿5,882 total
includes taxes & fees
11 Jun - 12 Jun
Blackberry River Inn
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers

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 ฿4,805
฿5,368 total
includes taxes & fees
14 Jun - 15 Jun
Hampton Inn & Suites Berkshires-Lenox
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 ฿2,154
฿2,413 total
includes taxes & fees
21 Jun - 22 Jun
Berkshire Travel Lodge
Seasonal outdoor pool

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (79 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
The price is ฿4,997
฿5,596 total
includes taxes & fees
15 Jun - 16 Jun
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.
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Choose what matters most at hotels with a pool in Sheffield

Breakfast included
4 stars

Top Sheffield Hotel Reviews

Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"Clean, neat. Loved the retro motel vibe. Perfect for a short visit or an overnight stay. Not much in the way of amenities, but places to eat and convenience stores within easy walking distance."
FREJ 3-night trip
Posted 20 hours ago
Monument Mountain Motel

Frequently asked questions

What are some accommodation options with pools in Sheffield?
Wilder House Berkshires: Features free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Features a seasonal outdoor pool, an indoor pool and buffet. Berkshires Untold: Provides 3 restaurants, an outdoor pool and spa services. The Yankee Inn: Features 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. Quality Inn Great Barrington: Features 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, 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 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.