Find Hotels with a Pool in Sheffield, MA
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Check availability on Sheffield Hotels with a Pool
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Aug 26 - Aug 27Tomorrow
Aug 27 - Aug 28This weekend
Aug 28 - Aug 30Next weekend
Sep 4 - Sep 6Our 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 IHGGreat Barrington
- Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
₩170,188
₩190,101 total
includes taxes & fees
Sep 23 - Sep 24
2. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
- Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
₩222,282
₩248,289 total
includes taxes & fees
Sep 7 - Sep 8
3. The Little Lion
The Little LionGreat Barrington
- Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
₩155,432
₩173,614 total
includes taxes & fees
Sep 13 - Sep 14
4. Little Cat Lodge
Little Cat LodgeCopake Falls
- Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
₩305,093
₩341,705 total
includes taxes & fees
Aug 27 - Aug 28
5. The Red Lion Inn
The Red Lion InnStockbridge
- Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
₩217,952
₩312,191 total
includes taxes & fees
Sep 8 - Sep 9
6. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
- Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
₩161,650
₩207,575 total
includes taxes & fees
Aug 31 - Sep 1
7. Blackberry River Inn
Blackberry River InnNorfolk
- Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
₩262,508
₩301,884 total
includes taxes & fees
Aug 30 - Aug 31
8. Prospect Berkshires
Prospect BerkshiresEgremont
- Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
₩454,526
₩554,065 total
includes taxes & fees
Sep 17 - Sep 18
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Top Sheffield Hotel Reviews
The Yankee Inn
10/10 Excellent
"Charming hotel with a wonderful breakfast and two lovely pools, plus a nature walk to a lake. The staff were great, really nice and helpful."
The Red Lion Inn
10/10 Excellent
"The room was very nice, super clean. Sitting on the porch is what we love most. Food was good, drinks a bit pricey..but when you're on vacation it hardly matters. The pool was nice, the hot tub too. A pleasant stay in a historic inn. It's the berkshires so its beautiful"
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."
Hampton Inn & Suites Berkshires-Lenox
10/10 Excellent
"We were there for one night and it worked out great. Nice breakfast!"
Howard Johnson by Wyndham Lenox
8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."