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

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Check availability on Sheffield Hotels with a Pool

Tonight
8 Oct - 9 Oct
Tomorrow
9 Oct - 10 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Sheffield hotels with a pool

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

1. 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.
AED 528
AED 589 total
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
An indoor swimming pool with clear lane markings, a poolside area with lounge chairs, and large windows allowing natural light.
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.
A modern bathroom with a large mirror, a sink, and a shower.

2. 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.
AED 364
AED 406 total
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
A white two-story house with a front door, windows, and a chimney.

3. 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.
AED 1,065
AED 1,285 total
includes taxes & fees
1 Nov - 2 Nov
The Old Inn On The Green
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 house with a stone patio and wooden stools.
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

4. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
AED 559
AED 626 total
includes taxes & fees
2 Nov - 3 Nov
Little Cat Lodge
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 bathroom with a toilet, sink, bathtub, and a glass-enclosed shower.
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

5. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
AED 551
AED 634 total
includes taxes & fees
1 Nov - 2 Nov
Blackberry River Inn
A poolside area with lounge chairs and a pool.
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.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.

6. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
AED 1,140
AED 1,397 total
includes taxes & fees
2 Nov - 3 Nov
Prospect 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 hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.

7. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
AED 380
AED 425 total
includes taxes & fees
18 Oct - 19 Oct
The Little Lion
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
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.

8. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
AED 579
AED 829 total
includes taxes & fees
3 Nov - 4 Nov
The Red Lion 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 building with a porch and multiple windows, surrounded by purple flowers.
A living room with a sofa, armchair, coffee table, and a patterned rug.

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
AED 430
AED 552 total
includes taxes & fees
12 Oct - 13 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A rectangular swimming pool with a metal ladder, surrounded by a black metal fence.
A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.
A wooden deck with a swing chair and a bench overlooking a lake.
A modern hotel room with a bed, sofa, leather chair, and a small table.

10. Interlaken Inn & Resort

Interlaken Inn & Resort
Lakeville
  • Immerse in the sun-drenched seasonal outdoor pool surrounded by lush resort grounds and full-service spa amenities.
AED 790
AED 909 total
includes taxes & fees
8 Nov - 9 Nov
Interlaken Inn & Resort
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
"Not enough bath clothes towels not enough outlets around the bed for people who have cpap or breathing problems."
Mark 1-night trip
Posted 7 hours ago
The Yankee Inn
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"
Joanne 1-night trip
Posted 1 day ago
The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted 3 days ago
Quality Inn Great Barrington
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"I was only there to sleep for a few hours"
Thomas 1-night trip
Posted 8 days ago
Courtyard by Marriott Lenox Berkshires

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.

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