10/12/22 SHEFFIELD FALLS, MA., USA - aerial view at sunrise of Sheffield Falls in autumn, Ma. with Housatonic River running through town, Berkshire Mountains

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Check availability on Sheffield Hotels with a Pool

Tonight
Oct 13 - Oct 14
Tomorrow
Oct 14 - Oct 15
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 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.
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.
₩191,744
₩214,179 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 hotel lobby with seating areas, tables, and a reception desk.
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.

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.
₩110,788
₩123,750 total
includes taxes & fees
Nov 10 - Nov 11
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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.

3. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
₩378,416
₩467,420 total
includes taxes & fees
Nov 10 - Nov 11
Prospect Berkshires
A poolside area with lounge chairs and blue umbrellas, surrounded by 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.
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.

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.
₩203,023
₩227,386 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 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.
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.
₩253,612
₩291,654 total
includes taxes & fees
Oct 14 - Oct 15
Blackberry River Inn
A large house with a balcony and a grassy yard.
A two-story building with a gabled roof and a chimney.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

6. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
₩138,152
₩154,315 total
includes taxes & fees
Oct 18 - Oct 19
The Little Lion
A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.
A building with a porch and multiple windows, surrounded by purple flowers.
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.

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.
₩156,172
₩200,540 total
includes taxes & fees
Oct 28 - Oct 29
Holiday Inn Club Vacations Oak n' Spruce Resort in the 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 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.

8. 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.
₩387,092
₩467,100 total
includes taxes & fees
Nov 1 - Nov 2
The Old Inn On The Green
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A covered porch with wicker furniture and hanging flower baskets.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

9. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
₩210,257
₩301,170 total
includes taxes & fees
Nov 3 - Nov 4
The Red Lion Inn
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 tented area with lush greenery and a dining setup.

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.
₩359,194
₩413,073 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

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"."
Kimberly 1-night trip
Posted 4 hours ago
Courtyard by Marriott Lenox Berkshires
The Yankee Inn

The Yankee Inn

8/10 Good
"Everything at the Yankee Inn was very good with the exception of, wasn’t the most comfortable bed I’ve ever slept in, but everything else was very good"
Mark 1-night trip
Posted 15 hours ago
The Yankee Inn
The Red Lion Inn

The Red Lion Inn

8/10 Good
"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."
Patricia 1-night trip
Posted 23 hours ago
The Red Lion Inn
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"It was good"
Vishva 1-night trip
Posted 2 days ago
Hampton Inn & Suites Berkshires-Lenox
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent
"Excellent room! Clean and good breakfast!"
Kelly 1-night trip
Posted 3 days ago
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Interlaken Inn & Resort

Interlaken Inn & Resort

10/10 Excellent
"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."
Suzanne 5-night trip
Posted 12 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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