Find Hotels with a Pool in Cheshire, MA
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Aug 30 - Aug 31Tomorrow
Aug 31 - Sep 1Next weekend
Sep 4 - Sep 6In two weeks
Sep 11 - Sep 13Our top choices for Cheshire hotels with a pool
1. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
- Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
₩133,053
₩163,718 total
includes taxes & fees
Sep 1 - Sep 2
2. The Springs Motel
The Springs MotelNew Ashford
- Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
₩168,773
₩185,144 total
includes taxes & fees
Aug 31 - Sep 1
3. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
- Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
₩162,408
₩181,415 total
includes taxes & fees
Sep 7 - Sep 8
4. Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
- Escape to a poolside oasis with a swim-up bar and the freedom to float from dawn to dusk.
₩116,370
₩129,982 total
includes taxes & fees
Sep 1 - Sep 2
5. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
₩130,196
₩176,176 total
includes taxes & fees
Aug 31 - Sep 1
6. Huttopia Berkshires
Huttopia BerkshiresWilliamstown
- Forest serenity and mountain trails define this Berkshires campground, complete with refreshing pool.
₩133,781
₩149,434 total
includes taxes & fees
Sep 8 - Sep 9
7. The Yankee Inn
The Yankee InnLenox
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
₩209,204
₩233,675 total
includes taxes & fees
Sep 27 - Sep 28
8. Jiminy Peak Mountain Resort
Jiminy Peak Mountain ResortHancock
- Ski-in/ski-out mountain resort with refreshing pool, hot tubs, and tennis courts awaits.
₩196,954
₩219,997 total
includes taxes & fees
Aug 31 - Sep 1
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Top Cheshire Hotel Reviews
Vacation Village in the Berkshires
10/10 Excellent
"Everything is excellent! WiFi was a bit spotty and kept dropping and reconnecting, but that doesn’t take away from my stay. A second fire pit would be great but again it doesn’t take away from my stay. Cost even beat out the “regular” usual brand hotels for what I feel like was a better location and more comfortable, and as a solo traveler it’s just right. I will keep coming back!"
The Yankee Inn
8/10 Good
"Independent option convenient to Tanglewood. Spacious room and facility. Breakfast included but needs better coffee and some other tweaks."
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!"