A covered wooden structure with a sloped roof, surrounded by greenery and trees.

Sheffield Hotel Guide - Hotels with Pool in Sheffield, Massachusetts

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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, (1,013 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is €148
includes taxes & fees
13 Jul - 14 Jul
The Yankee Inn
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (881 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is €97
includes taxes & fees
13 Jul - 14 Jul
Howard Johnson by Wyndham Lenox
Indoor pool

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, (789 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is €151
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,013 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is €206
includes taxes & fees
22 Jul - 23 Jul
The Red Lion Inn
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (489 reviews)
  • cleanliness
    Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
The price is €66
includes taxes & fees
13 Jul - 14 Jul
Berkshire Travel Lodge
Seasonal outdoor pool

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (96 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
The price is €167
includes taxes & fees
16 Jul - 17 Jul
Little Cat Lodge
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, (794 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
The price is €190
includes taxes & fees
10 Aug - 11 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Seasonal outdoor pool

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (304 reviews)
  • cleanliness
    Immerse in the sun-drenched seasonal outdoor pool surrounded by lush resort grounds and full-service spa amenities.
The price is €271
includes taxes & fees
26 Jul - 27 Jul
Interlaken Inn & Resort
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (581 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is €110
includes taxes & fees
14 Jul - 15 Jul
The Little Lion
Indoor pool

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (691 reviews)
  • cleanliness
    Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
The price is €206
includes taxes & fees
19 Jul - 20 Jul
Hilton Garden Inn Lenox Pittsfield
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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"I found the staff very helpful, especially the young man who worked over night. We experienced a slight problem, and he could not have been nicer. He represented the hotel extremely well. Breakfast was uninspiring but generally good. The view from the breakfast room is lovely. The common areas seem a little tired, but the room was very good value - especially as we overlooked the lake. The location is wonderful for Lee, Lenox, Stockbridge, all the cultural centers and the Mass Pike. A beach is adjacent for swimming. We plan to return next year."
Susan 4-night trip
Posted 14 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions

What are some accommodation options with pools in Sheffield?
Wilder House Berkshires: Offers a seasonal outdoor pool, an indoor pool and buffet. The Yankee Inn: Provides free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Offers 3 restaurants, an outdoor pool and spa services. Berkshires Untold: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. The Red Lion Inn: Provides 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli.
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, Bartholomew's Cobble and Mount Everett State Reservation 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.