Hotels with Swimming Pool in Stockbridge, Massachusetts
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Sep 9 - Sep 10Tomorrow
Sep 10 - Sep 11This weekend
Sep 11 - Sep 13Next weekend
Sep 18 - Sep 20Our top choices for Stockbridge hotels with a pool
1. The Red Lion Inn
The Red Lion InnStockbridge
- Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
P9,921
P14,194 total
includes taxes & fees
Sep 30 - Oct 1
2. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and ChesterwoodStockbridge
- Seasonal outdoor pool retreat at this colonial b&b invites lounging amid gardens and historic charm.
P20,680
P25,017 total
includes taxes & fees
Sep 28 - Sep 29
3. The Inn at Stockbridge
The Inn at StockbridgeStockbridge
- Seasonal outdoor pool beckons for refreshing summer dips at this upscale bed and breakfast in Stockbridge.
P23,612
P27,694 total
includes taxes & fees
Sep 14 - Sep 15
4. 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.
P7,328
P9,410 total
includes taxes & fees
Sep 13 - Sep 14
5. The Yankee Inn
The Yankee InnLenox
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
P7,266
P8,116 total
includes taxes & fees
Sep 22 - Sep 23
6. 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.
P8,268
P9,235 total
includes taxes & fees
Sep 15 - Sep 16
7. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
P4,986
P6,968 total
includes taxes & fees
Oct 1 - Oct 2
8. The Little Lion
The Little LionGreat Barrington
- Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
P7,044
P7,868 total
includes taxes & fees
Sep 20 - Sep 21
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Top Stockbridge Hotel Reviews
Vacation Village in the Berkshires
10/10 Excellent
"Always a great stay at. Vacation Villages"
The Yankee Inn
10/10 Excellent
"Excellent in every way. Service, staff, amenities. Everything was perfect."
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"Generous front desk (forgot toothbrush & comb, they gave us both free of charge). Great complimentary breakfast & tea/coffee machine. Great WiFi. Beautiful view & kayaking was so fun. We had a wonderful stay!"
Jiminy Peak Mountain Resort
10/10 Excellent
"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"
The Inn at Stockbridge
10/10 Excellent
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
10/10 Excellent
"My stay at Diane’s bed and breakfast was absolutely wonderful. Diane herself is incredibly warm, welcoming, and genuinely informative — she made the entire experience feel personal and cared for. The room was quaint, cozy, and charming in that classic New England way, with comfortable beds, plenty of towels, and a generous selection of bath amenities that made settling in effortless. Breakfast was a standout: a truly amazing cook‑to‑order meal that felt both homemade and high‑end. Every dish was fresh, delicious, and clearly prepared with pride. Parking was plentiful and convenient, making arrival and departure stress‑free. Overall, this B&B is a gem — comfortable, inviting, and thoughtfully run. I’d happily return and recommend it to anyone looking for a relaxing stay."