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

Hotels with Pool & Resorts in Sheffield from NZ$165

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Check availability on Sheffield Hotels with Pool

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

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.
NZ$286
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 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.
NZ$165
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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.

3. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
NZ$268
includes taxes & fees
11 Nov - 12 Nov
Little Cat Lodge
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 cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.
A bathroom with a toilet, sink, bathtub, and a glass-enclosed shower.

4. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
NZ$389
includes taxes & fees
14 Oct - 15 Oct
Blackberry River Inn
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.

5. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
NZ$206
includes taxes & fees
18 Oct - 19 Oct
The Little Lion
A dining area with round tables set for two, a fireplace, and a mural on the wall.
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.
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.

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.
NZ$623
includes taxes & fees
1 Nov - 2 Nov
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 bar with wooden floors and shelves filled with bottles.
A covered porch with wicker furniture and hanging flower baskets.

7. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
NZ$402
includes taxes & fees
3 Nov - 4 Nov
The Red Lion 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 lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
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.
NZ$627
includes taxes & fees
10 Nov - 11 Nov
Prospect Berkshires
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.

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.
NZ$268
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

10. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
NZ$211
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
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Choose what matters most at hotels with a pool in Sheffield

Breakfast included
4 stars
5 stars
Spa pool
Spa

Top Sheffield Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"O"
Ilya 2-night trip
Posted 7 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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 7 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Beds were comfortable, room was clean, train was not often"
Patricia 3-night trip
Posted 9 hours ago
Quality Inn Great Barrington
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 15 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 1 day 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 11 days ago
Interlaken Inn & Resort

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. 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 swimming pools, 2 outdoor swimming pools and a snack bar/deli. The Yankee Inn: 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 19°C, while the coldest months are January and February, with an average of -2°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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