A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

Find Hotels with a Pool in Sheffield, MA

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Check availability on Sheffield Hotels with a Pool

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Sheffield hotels with a pool

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

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, (819 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
The price is ￥22,695
￥25,349 total
includes taxes & fees
Nov 3 - Nov 4
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

2. 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, (847 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is ￥14,199
￥15,860 total
includes taxes & fees
Nov 12 - Nov 13
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A poolside area with white lounge chairs and a red umbrella.

3. Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
10.0 out of 10, Exceptional, (48 reviews)
  • cleanliness
    Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
The price is ￥43,833
￥54,248 total
includes taxes & fees
Nov 29 - Nov 30
Prospect Berkshires
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

4. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (150 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
The price is ￥23,997
￥26,877 total
includes taxes & fees
Nov 12 - Nov 13
Little Cat Lodge
An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.

5. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
The price is ￥19,737
￥25,130 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A large house with a balcony and a grassy yard.

6. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (636 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is ￥13,245
￥14,795 total
includes taxes & fees
Nov 1 - Nov 2
The Little Lion
An outdoor patio with wicker furniture and a small table, surrounded by a garden and trees.

7. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (251 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is ￥27,878
￥32,060 total
includes taxes & fees
Nov 1 - Nov 2
Blackberry River Inn
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

8. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,006 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is ￥24,852
￥35,597 total
includes taxes & fees
Nov 8 - Nov 9
The Red Lion Inn
A white two-story house with a front door, windows, and a chimney.

9. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (95 reviews)
  • cleanliness
    Dive into summer luxury at this historic inn's outdoor pool surrounded by garden serenity and natural wonders.
The price is ￥45,753
￥55,210 total
includes taxes & fees
Nov 1 - Nov 2
The Old Inn On The Green
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

10. 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 ￥16,077
￥17,959 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee 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.
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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
"We had a wonderful stay over the weekend. Bed VERY comfortable. Quiet, except one early am with kids running in the halls! Parents issue! Breakfast was good. Several items needing to be replenished each am. Had to go and ask the girls a few times. They were in the back room eating, seemingly unaware of restocking needed items. The bar on the weekend was an extra perk! Loved Carl 💕, the bartender , quite a conversationalist. Overall beautiful location , walking path in the back was nice, in the back of the hotel."
Erin 3-night trip
Posted 21 hours ago
The Yankee Inn

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. Antique Farmhouse Totally Restored: Offers a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge: Offers 3 restaurants, an outdoor pool, and spa services. Quality Inn Great Barrington: Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli. The Yankee Inn: 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 Suter Farm, Ashley House, and Thom Reed UFO Monument Park 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.