Find Hotels with a Pool in Sheffield, MA

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Check availability on Sheffield Hotels with a Pool

Our top choices for Sheffield hotels with a pool

Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (897 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is AED 318
AED 437 total
includes taxes & fees
10 May - 11 May
Berkshire Mountain Lodge
Indoor pool

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 AED 525
AED 587 total
includes taxes & fees
15 Apr - 16 Apr
Element Lenox Berkshires
Exterior

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 AED 404
AED 451 total
includes taxes & fees
13 Apr - 14 Apr
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, (846 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is AED 290
AED 324 total
includes taxes & fees
18 Apr - 19 Apr
Howard Johnson by Wyndham Lenox
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, (1,000 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is AED 407
AED 454 total
includes taxes & fees
14 Apr - 15 Apr
Hampton Inn & Suites Berkshires-Lenox
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (88 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is AED 433
AED 484 total
includes taxes & fees
16 Apr - 17 Apr
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Seasonal outdoor pool

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 AED 560
AED 645 total
includes taxes & fees
21 Apr - 22 Apr
Blackberry River Inn
Property grounds

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 AED 493
AED 714 total
includes taxes & fees
12 Apr - 13 Apr
The Red Lion Inn
Seasonal outdoor pool

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 AED 367
AED 410 total
includes taxes & fees
17 Apr - 18 Apr
Sunset Inn
Indoor pool

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (776 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
The price is AED 558
AED 624 total
includes taxes & fees
14 Apr - 15 Apr
Fairfield Inn & Suites by Marriott Great Barrington 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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Friendly staff, clean room, good breakfast"
Andrii 3-night trip
Posted 11 hours ago
Quality Inn Great Barrington

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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. Luxury Private Estate in the Berkshires | Whitney by AvantStay: Hotel located near National Shrine of the Divine Mercy. Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Berkshire Mountain Lodge: Features a seasonal outdoor pool, an indoor pool, and buffet. Berkshires Untold: Hotel, 15-minute walk from National Shrine of the Divine Mercy. Provides 3 restaurants, an outdoor pool, and spa services. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: 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.