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

Hotels with Swimming Pool in Sheffield, Massachusetts

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Check availability on Sheffield Hotels with Swimming Pool

Tonight
Aug 20 - Aug 21
Tomorrow
Aug 21 - Aug 22
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Sheffield hotels with a pool

An indoor swimming pool with clear water, surrounded by chairs and tables, large windows, and a tiled floor.
A buffet with labeled containers for omelets and other dishes.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A Holiday Inn Express & Suites building with a stone facade, a covered entrance, and a parking lot.

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.
P7,091
P7,920 total
includes taxes & fees
Sep 20 - Sep 21
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 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.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

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.
P12,002
P13,406 total
includes taxes & fees
Sep 20 - Sep 21
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A large house with a balcony and a grassy yard.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.
A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

3. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
P6,937
P7,748 total
includes taxes & fees
Sep 1 - Sep 2
The Little Lion
A large indoor swimming pool with clear water, surrounded by walls with informational posters and a reception area with a 'Welcome' sign.
A serene riverside view with a stone bridge, reflecting trees and buildings.
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.

4. 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.
P7,214
P9,264 total
includes taxes & fees
Sep 21 - Sep 22
Holiday Inn Club Vacations Oak 'n Spruce Resort
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.
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.
A house with a stone patio and wooden stools.

5. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
P13,596
P15,227 total
includes taxes & fees
Sep 20 - Sep 21
Little Cat Lodge
A backyard with a swimming pool, lounge chairs, and a hot tub.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A bar with wooden floors and shelves filled with bottles.
A covered porch with wicker furniture and hanging flower baskets.

6. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
P10,282
P14,556 total
includes taxes & fees
Sep 14 - Sep 15
The Red Lion Inn
An outdoor patio with wicker furniture and a small table, surrounded by a garden and trees.
A grand hallway with a chandelier, a staircase, and a table with flowers.
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.
A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.

7. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
P11,715
P13,472 total
includes taxes & fees
Sep 1 - Sep 2
Blackberry River 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 cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

8. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
P20,308
P24,755 total
includes taxes & fees
Sep 17 - Sep 18
Prospect Berkshires
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
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
Great Barrington
  • Dive into summer luxury at this historic inn's outdoor pool surrounded by garden serenity and natural wonders.
P19,709
P23,783 total
includes taxes & fees
Sep 1 - Sep 2
The Old Inn On The Green
A swimming pool with a fenced area, lounge chairs, and a warning sign.
A hotel room with two beds, a chair, and a bedside table with a phone.
A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.

10. Sunset Inn

Sunset Inn
Lee
  • Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
P6,120
P6,836 total
includes taxes & fees
Sep 1 - Sep 2
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

8/10 Good
"Excellent staff interaction. Great price and excellent location."
Irene 2-night trip
Posted 2 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

8/10 Good
"The staff were all very nice and polite."
ella 1-night trip
Posted 8 hours ago
Hampton Inn & Suites Berkshires-Lenox
The Yankee Inn

The Yankee Inn

10/10 Excellent
"What a wonderful stay! It was an impromptu overnight to the Berkshires and I’m so glad we chose to stay here. Our room was beautiful and clean, with a lovely view of the pond area out back from the balcony. Great bathroom and shower, very clean. Breakfast was yummy with a nice selection. The pools and hot tub were the BEST part. I absolutely will be back because one night was certainly not enough."
Kelly 1-night trip
Posted 22 hours ago
The Yankee Inn

Frequently asked questions

What are some accommodations 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 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 Three Mile Pond Wildlife Management Area, Suter Farm, 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.

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