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

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Check availability on Sheffield Hotels with a Pool

Tonight
Oct 19 - Oct 20
Tomorrow
Oct 20 - Oct 21
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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 room with two beds, a desk, a television, and a dresser.
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.

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.
NT$4,654
NT$5,199 total
includes taxes & fees
Nov 2 - Nov 3
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 modern bathroom with a large mirror, a sink, and a shower.
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.

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.
NT$2,689
NT$3,004 total
includes taxes & fees
Nov 17 - Nov 18
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A poolside area with lounge chairs and a pool.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.
A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

3. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
NT$9,186
NT$11,346 total
includes taxes & fees
Nov 9 - Nov 10
Prospect Berkshires
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 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.
NT$4,928
NT$5,520 total
includes taxes & fees
Nov 2 - Nov 3
Little Cat Lodge
An outdoor patio with wicker furniture and a small table, surrounded by a garden and trees.
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.
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.
NT$6,156
NT$7,080 total
includes taxes & fees
Oct 20 - Oct 21
Blackberry River Inn
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 white two-story house with a front door, windows, and a chimney.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

6. 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.
NT$9,396
NT$11,338 total
includes taxes & fees
Nov 1 - Nov 2
The Old Inn On The Green
A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A building with a porch and multiple windows, surrounded by purple flowers.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

7. 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.
NT$3,791
NT$4,868 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A large house with a balcony and a grassy yard.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
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.

8. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
NT$3,354
NT$3,746 total
includes taxes & fees
Oct 20 - Oct 21
The Little Lion
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
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.

9. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
NT$5,104
NT$7,311 total
includes taxes & fees
Nov 4 - Nov 5
The Red Lion Inn
A rectangular swimming pool with a metal ladder, surrounded by a black metal fence.
A modern hotel room with a bed, sofa, leather chair, and a small table.
A tented area with lush greenery and a dining setup.
A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.

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.
NT$8,719
NT$10,027 total
includes taxes & fees
Nov 8 - Nov 9
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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Everything about the property was excellant, clean,helpful Thank you very much"
Debra 1-night trip
Posted 17 hours ago
Hampton Inn & Suites Berkshires-Lenox
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"The room was clean and property was well maintained."
Ronald 1-night trip
Posted 18 hours ago
Courtyard by Marriott Lenox Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"-"
Serena 1-night trip
Posted 21 hours ago
Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

8/10 Good
"Lovely, super clean unit with nice furnishings, however, the dining chair cushions need a good cleaning as the dirt could be seen. There also was candy/gum stuck to one of the cushions and another cushion was completely loose from the chair. There was mention of a "two-burner hotplate" in the description, but the photos showed a two-burner electric stove top. What actually is there is a two-burner infared hotplate. Instructions on how to use it is posted on the wall above the sink, not on the wall above the hotplate. Unfortunately, we were assigned an end unit in Building #13, which is currently being renovated. There was a family occupying the unit above us. The children ran up and down the stair and allowed the outside door to slam each and every time until late in the evening. No noise during quiet hours though. :o)"
Julio 1-night trip
Posted 22 hours ago
The Yankee Inn
Interlaken Inn & Resort

Interlaken Inn & Resort

10/10 Excellent
"Over eight annual visits to this hotel, it has been a wonderful stay each time."
mary 1-night trip
Posted 2 days ago
Interlaken Inn & Resort

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. Berkshire Mountain Lodge: Offers a seasonal outdoor pool, an indoor pool, and buffet. Quality Inn Great Barrington: Offers 3 restaurants, an outdoor pool, and spa services. The Yankee Inn: Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Berkshires Untold: 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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