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

Sheffield Hotel with Pool

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Sheffield Hotel with Pool

This weekend
7 Aug - 9 Aug
Next weekend
14 Aug - 16 Aug

Our top choices for Sheffield hotels with a pool

Indoor pool

1. 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, (799 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
The price is HK$1,526
HK$1,705 total
includes taxes & fees
31 Aug - 1 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Living area

2. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (200 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is HK$1,490
HK$1,714 total
includes taxes & fees
13 Aug - 14 Aug
Blackberry River Inn
Indoor pool

3. 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, (798 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is HK$1,184
HK$1,323 total
includes taxes & fees
31 Aug - 1 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Seasonal outdoor pool

4. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (114 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
The price is HK$1,729
HK$1,937 total
includes taxes & fees
6 Aug - 7 Aug
Little Cat Lodge
Exterior

5. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (596 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is HK$882
HK$986 total
includes taxes & fees
1 Sept - 2 Sept
The Little Lion
2 indoor pools, 2 outdoor pools, pool umbrellas, pool loungers

6. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
3.5 star property
South Lee
9.2 out of 10, Wonderful, (947 reviews)
  • cleanliness
    Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
The price is HK$1,052
HK$1,328 total
includes taxes & fees
31 Aug - 1 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
Breakfast, lunch, dinner and brunch served

7. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
  • cleanliness
    Dive into summer luxury at this historic inn's outdoor pool surrounded by garden serenity and natural wonders.
The price is HK$2,500
HK$3,017 total
includes taxes & fees
1 Sept - 2 Sept
The Old Inn On The Green
Exterior

8. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (892 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is HK$620
HK$692 total
includes taxes & fees
30 Aug - 31 Aug
Howard Johnson by Wyndham Lenox
Seasonal outdoor pool

9. Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (307 reviews)
  • cleanliness
    Immerse in the sun-drenched seasonal outdoor pool surrounded by lush resort grounds and full-service spa amenities.
The price is HK$1,899
HK$2,184 total
includes taxes & fees
30 Aug - 31 Aug
Interlaken Inn & Resort
Outdoor pool, pool loungers

10. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,007 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is HK$1,373
HK$1,924 total
includes taxes & fees
27 Aug - 28 Aug
The Red Lion Inn
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.
View all properties

Choose what matters most at hotels with a pool in Sheffield

Breakfast included
4 stars

Top Sheffield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Escaped into another world on each floor's hallway-the memorabilia and artwork spoke of an honest, New England history. The atmosphere was perfect for a genuine, original immersion into New England's past and LOVED going up and down the 150yr old elevator! Meals delicious w/excellent service. Only one issue we had: the AC in the room was difficult to adjust and were quite chilled even w/turning the thermostat up to 80 deg!!!!!!!!! as suggested by the front desk. Shall make this a yearly visit!"
judy 1-night trip
Posted 7 hours ago
The Red Lion Inn

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 buffet, an indoor pool and complimentary high-speed (wired) Internet access. Berkshires Untold: Features 3 restaurants, an outdoor pool and spa services. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG: Provides free self parking, an outdoor pool and flat-screen televisions.
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, Three Mile Pond Wildlife Management Area and Suter Farm 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.

Explore a world of travel with Expedia