
Search Hotels with Pool in Stockbridge
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check availability on Stockbridge Hotels with Pool
Tonight
12 Sep - 13 SepTomorrow
13 Sep - 14 SepNext weekend
18 Sep - 20 SepIn two weeks
25 Sep - 27 SepOur 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.
4.174.157 ₫
5.950.240 ₫ total
includes taxes & fees
23 Sept - 24 Sept




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.
8.558.006 ₫
10.352.703 ₫ total
includes taxes & fees
28 Sept - 29 Sept




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.
9.771.322 ₫
11.460.528 ₫ total
includes taxes & fees
14 Sept - 15 Sept




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.
3.032.406 ₫
3.893.895 ₫ total
includes taxes & fees
14 Sept - 15 Sept




5. The Yankee Inn
The Yankee InnLenox
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
3.006.720 ₫
3.358.507 ₫ total
includes taxes & fees
22 Sept - 23 Sept




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.
3.473.012 ₫
3.879.406 ₫ total
includes taxes & fees
20 Sept - 21 Sept




7. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
2.063.214 ₫
2.883.664 ₫ total
includes taxes & fees
1 Oct - 2 Oct




8. The Little Lion
The Little LionGreat Barrington
- Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
2.915.775 ₫
3.256.920 ₫ total
includes taxes & fees
14 Sept - 15 Sept
View all properties
Top Stockbridge Hotel Reviews
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"Great staff great restaurant!"
Howard Johnson by Wyndham Lenox
10/10 Excellent
"The staff was extremely friendly. Did see several areas in the room that were dusty. Stains on the wallpaper and some wallpaper chipping off."
The Yankee Inn
10/10 Excellent
"Nasically a large motel with both an outdoor and indoor pool. A bit tired, but reasonably close to Lenox and to Tabglewood."
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!"







