Hotels with Swimming Pool in The Berkshires, Massachusetts
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Aug 31 - Sep 1Tomorrow
Sep 1 - Sep 2This weekend
Sep 4 - Sep 6Next weekend
Sep 11 - Sep 13Our top choices for The Berkshires hotels with a pool
1. The Yankee Inn
The Yankee InnLenox
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
P5,383
P6,012 total
includes taxes & fees
Sep 28 - Sep 29
2. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
P5,005
P6,982 total
includes taxes & fees
Oct 1 - Oct 2
3. 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.
P7,285
P9,354 total
includes taxes & fees
Sep 7 - Sep 8
4. The Red Lion Inn
The Red Lion InnStockbridge
- Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
P9,808
P14,048 total
includes taxes & fees
Sep 29 - Sep 30
5. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
- Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
P6,019
P7,406 total
includes taxes & fees
Sep 2 - Sep 3
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.
P7,160
P7,998 total
includes taxes & fees
Sep 7 - Sep 8
7. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
- Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
P7,676
P8,574 total
includes taxes & fees
Sep 13 - Sep 14
8. 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.
P10,003
P11,173 total
includes taxes & fees
Sep 7 - Sep 8
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Hotels with pools and free breakfast in The Berkshires
P5,383
P6,012 total
includes taxes & fees
Sep 28 - Sep 29
Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
P7,285
P9,354 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
P7,160
P7,998 total
includes taxes & fees
Sep 7 - Sep 8
P7,676
P8,574 total
includes taxes & fees
Sep 13 - Sep 14
P11,151
P13,847 total
includes taxes & fees
Sep 8 - Sep 9
P4,919
P5,494 total
includes taxes & fees
Sep 1 - Sep 2
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
P10,003
P11,173 total
includes taxes & fees
Sep 7 - Sep 8
P11,061
P12,355 total
includes taxes & fees
Sep 7 - Sep 8
P11,083
P12,380 total
includes taxes & fees
Sep 7 - Sep 8
P9,225
P10,304 total
includes taxes & fees
Oct 1 - Oct 2
4-star hotels with pools in The Berkshires
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
P20,557
P24,868 total
includes taxes & fees
Sep 28 - Sep 29
P23,472
P27,530 total
includes taxes & fees
Sep 13 - Sep 14
P24,220
P27,054 total
includes taxes & fees
Sep 3 - Sep 4
P19,850
P23,953 total
includes taxes & fees
Sep 1 - Sep 2
P15,890
P17,749 total
includes taxes & fees
Sep 13 - Sep 14
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all propertiesTop The Berkshires Hotel Reviews
Holiday Inn Express Hotel & Suites Great Barrington by IHG
10/10 Excellent
"This facility appeared to be brand new. Breakfast was excellent and the dining area was spacious and attractive. We would definitely recommend this hotel and will stay here again when we are back in the area!"
Jiminy Peak Mountain Resort
10/10 Excellent
"Nice to have a kitchenette to cook in"
Quality Inn Great Barrington
10/10 Excellent
"Location"
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!"