Hotels with Swimming Pool in Cheshire, Massachusetts
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Aug 23 - Aug 24Tomorrow
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Aug 28 - Aug 30In two weeks
Sep 4 - Sep 6Our 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.
P5,361
P6,665 total
includes taxes & fees
Aug 31 - Sep 1
2. The Springs Motel
The Springs MotelNew Ashford
- Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
P7,359
P8,073 total
includes taxes & fees
Aug 24 - Aug 25
3. The Yankee Inn
The Yankee InnLenox
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
P9,751
P10,891 total
includes taxes & fees
Sep 14 - Sep 15
4. 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.
P7,344
P8,203 total
includes taxes & fees
Sep 21 - Sep 22
5. Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
- Poolside bliss awaits with mountain views in this rejuvenating indoor pool and hot tub retreat.
P9,180
P10,254 total
includes taxes & fees
Sep 1 - Sep 2
6. Cozy Corner Motel
Cozy Corner MotelWilliamstown
- Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
P5,443
P6,398 total
includes taxes & fees
Sep 9 - Sep 10
7. 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.
P6,390
P7,138 total
includes taxes & fees
Aug 24 - Aug 25
8. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
P5,838
P7,900 total
includes taxes & fees
Aug 31 - Sep 1
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Top Cheshire Hotel Reviews
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"I liked the balcony overlooking the lake"
The Yankee Inn
8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Vacation Village in the Berkshires
8/10 Good
"Price - quality =awesome"
The Red Lion Inn
10/10 Excellent
"We loved our stay here. It’s not a modern cookie cutter experience. We loved the history and antique nature of the property."
Howard Johnson by Wyndham Lenox
8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Holiday Inn & Suites Pittsfield-Berkshires by IHG
8/10 Good
"I had 2 rooms. 1 room (414) did not have a phone, the microwave didn't have power. The other room was fine. We didn't like that there was only 1 elevator working as we had to wait quite a while sometimes to go up or down. We understand that the hotel is undergoing renovations. Overall, we enjoyed our stay."