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

Hotels with Pool & Resorts in Sheffield from NZ$207

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Check availability on Sheffield Hotels with Pool

Tonight
28 Aug - 29 Aug
Tomorrow
29 Aug - 30 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Sheffield hotels with a pool

1. 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$216
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG

2. 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$301
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

3. 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$207
includes taxes & fees
10 Sept - 11 Sept
The Little Lion

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.
NZ$337
includes taxes & fees
31 Aug - 1 Sept
Little Cat Lodge

5. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
NZ$367
includes taxes & fees
29 Sept - 30 Sept
The Red Lion Inn

6. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
NZ$252
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort

7. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
NZ$344
includes taxes & fees
29 Sept - 30 Sept
Blackberry River Inn

8. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
NZ$673
includes taxes & fees
7 Sept - 8 Sept
Prospect Berkshires

9. 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$646
includes taxes & fees
1 Sept - 2 Sept
The Old Inn On The Green

10. Sunset Inn

Sunset Inn
Lee
  • Splash into a seasonal outdoor pool near Tanglewood Music Centre, offering a sunny retreat in a peaceful location.
NZ$175
includes taxes & fees
29 Sept - 30 Sept
Sunset 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 Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
Dorothy 1-night trip
Posted 1 hour ago
The Red Lion Inn
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"I am not a person who usually writes a review but I loved the place. Room was great. Staff was great. I had never been to an Indian restaurant but everywhere I went people raved about I so we went and it was wonderful. Only a few small issues. The fan in our bathroom room needs attention. Very loud. Something is failing. The wifi was very weak in my room. Kept cutting out. and just one other suggestion. The balcony on the upper level should have privacy screens on the sides. Other wise I would absolutely go back."
JAMES 2-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

10/10 Excellent
"One of the quietest rooms we have ever stayed in. The location was very convenient to sites in both Lenox and Stockbridge."
Stacia 1-night trip
Posted 1 day ago
The Yankee Inn
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"It was much better than expected. Subtle lighting in the room was a nice touch. Clean and very comfortable bedding and bathroom. Everything in the fitness room was was clean and operational. The breakfast was superb. A very enjoyable stay."
William 1-night trip
Posted 3 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"We were there for one night and it worked out great. Nice breakfast!"
Erlinde 1-night trip
Posted 5 days ago
Hampton Inn & Suites Berkshires-Lenox

Frequently asked questions

What are some accommodation options with pools in Sheffield?
Wilder House Berkshires: Offers a seasonal outdoor pool, an indoor pool and buffet. The Yankee Inn: Provides free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. Berkshires Untold: Features 3 restaurants, an outdoor pool and spa services. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG: Provides free self parking, an outdoor pool and flat-screen televisions.
What is there to see and do in Sheffield?
Spend some time experiencing the great outdoors at Housatonic River. Discover sights such as Three Mile Pond Wildlife Management Area, Ashley House and Mount Everett State Reservation 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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