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

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Check availability on Sheffield Hotels with Pool

Tonight
9 Sep - 10 Sep
Tomorrow
10 Sep - 11 Sep
This weekend
11 Sep - 13 Sep
Next weekend
18 Sep - 20 Sep

Our top choices for Sheffield hotels with a pool

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A breakfast area with a counter, coffee machine, and a display of pastries.
A modern hotel lobby with seating areas, tables, and a reception desk.

1. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
  • Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
฿4,343
฿4,852 total
includes taxes & fees
15 Sept - 16 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A hotel room with two beds, a desk, a television, and a dresser.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

2. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
  • Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
฿6,123
฿6,839 total
includes taxes & fees
17 Sept - 18 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
A house with a stone patio and wooden stools.
A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

3. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
฿5,891
฿6,598 total
includes taxes & fees
10 Sept - 11 Sept
Little Cat Lodge
A large house with a balcony and a grassy yard.
A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.
A two-story building with a gabled roof and a chimney.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

4. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
฿3,700
฿4,133 total
includes taxes & fees
13 Sept - 14 Sept
The Little Lion
An outdoor patio with wicker furniture and a small table, surrounded by a garden and trees.
A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.
A grand hallway with a chandelier, a staircase, and a table with flowers.

5. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
฿4,934
฿5,674 total
includes taxes & fees
10 Sept - 11 Sept
Blackberry River Inn
A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

6. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
฿3,848
฿4,942 total
includes taxes & fees
13 Sept - 14 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
A backyard with a swimming pool, lounge chairs, and a hot tub.
A covered porch with wicker furniture and hanging flower baskets.
A bar with wooden floors and shelves filled with bottles.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

7. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
฿5,212
฿7,456 total
includes taxes & fees
30 Sept - 1 Oct
The Red Lion Inn
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.

8. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
฿3,815
฿4,262 total
includes taxes & fees
22 Sept - 23 Sept
The Yankee Inn
A poolside area with lounge chairs and a pool.
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.

9. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
฿10,805
฿13,171 total
includes taxes & fees
10 Sept - 11 Sept
Prospect Berkshires
A swimming pool with a fenced area, lounge chairs, and a warning sign.
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.
A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.
A covered corridor with a metal railing, white walls, and a view of a street with parked cars.

10. Sunset Inn

Sunset Inn
Lee
  • Splash into a seasonal outdoor pool near Tanglewood Music Centre, offering a sunny retreat in a peaceful location.
฿3,019
฿3,373 total
includes taxes & fees
28 Sept - 29 Sept
Sunset Inn
View all properties

Choose what matters most at hotels with a pool in Sheffield

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Sheffield Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Was very recently renovated and done quite well."
Robert 1-night trip
Posted 5 hours ago
The Yankee Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"We were in town for a concert and skeptical at first but when we arrived at our room it was very clean, the front desk was quick and pleasant, would definitely recommend as a nice place to stay!"
COLLEEN 1-night trip
Posted 11 hours ago
Howard Johnson by Wyndham Lenox
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"The room was clean and comfortable and the pool was well heated (though small). I liked the breakfast options. Good location too."
Bella 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"Black swann is great hotel with very helpful staff. They also have a Indian restaurant inside the hotel with lake view. It is a bit pricey but their fish curry is a must try!! I had it twice in a row and I am very picky eater."
Dheeraj 3-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"Stayed for only one night after Tanglewood concert. Clean, modern room. Close driving proximity to everything. Friendly staff checking in and out. I’d stay here again."
Louise 1-night trip
Posted 2 days ago
Courtyard by Marriott Lenox Berkshires

Frequently asked questions

What are some accommodation options with pools in Sheffield?
Wilder House Berkshires: Provides free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Features a seasonal outdoor pool, an indoor pool and buffet. The Yankee Inn: Features 3 restaurants, an outdoor pool and spa services. Berkshires Untold: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. The Red Lion Inn: Features 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 Three Mile Pond Wildlife Management Area, 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 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.

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