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

Sheffield Hotels with Swimming Pool

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Check availability on Sheffield Hotels with Swimming Pools

Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 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 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.
RM587
RM656 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 modern bathroom with a large mirror, a sink, and a shower.
A modern hotel lobby with seating areas, tables, and a reception desk.
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.
RM388
RM434 total
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 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.

3. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
RM613
RM705 total
includes taxes & fees
14 Oct - 15 Oct
Blackberry River Inn
A poolside area with lounge chairs and blue umbrellas, surrounded by 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.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.

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.
RM622
RM696 total
includes taxes & fees
2 Nov - 3 Nov
Little Cat Lodge
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 white two-story house with a front door, windows, and a chimney.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

5. 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.
RM1,185
RM1,430 total
includes taxes & fees
1 Nov - 2 Nov
The Old Inn On The Green
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.

6. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
RM1,269
RM1,554 total
includes taxes & fees
2 Nov - 3 Nov
Prospect 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 sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.
A two-story building with a gabled roof and a chimney.

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.
RM423
RM472 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 large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

8. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
RM644
RM922 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 living room with a sofa, armchair, coffee table, and a patterned rug.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

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.
RM456
RM589 total
includes taxes & fees
8 Oct - 9 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 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.
RM879
RM1,011 total
includes taxes & fees
26 Oct - 27 Oct
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 Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great staff, heated bathroom floors."
Ellen 3-night trip
Posted 22 hours ago
The Red Lion Inn
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 4 days ago
Interlaken Inn & Resort
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 7 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: 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 swimming pools, 2 outdoor swimming pools and a snack bar/deli. Berkshires Untold: Features buffet, an indoor pool and complimentary high-speed (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 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 19Β°C, while the coldest months are January and February, with an average of -2Β°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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