Cheshire Hotel Guide - Hotels with Pool in Cheshire, Massachusetts
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Cheshire Hotels with Pool
Tonight
25 Aug - 26 AugTomorrow
26 Aug - 27 AugThis weekend
28 Aug - 30 AugNext weekend
4 Sept - 6 SeptOur 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.
€93
includes taxes & fees
31 Aug - 1 Sept
2. The Springs Motel
The Springs MotelNew Ashford
- Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
€115
includes taxes & fees
9 Sept - 10 Sept
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.
€114
includes taxes & fees
23 Sept - 24 Sept
4. 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.
€142
includes taxes & fees
1 Sept - 2 Sept
5. Huttopia Berkshires
Huttopia BerkshiresWilliamstown
- Forest serenity and mountain trails define this Berkshires campground, complete with refreshing pool.
€93
includes taxes & fees
8 Sept - 9 Sept
6. The Yankee Inn
The Yankee InnLenox
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
€151
includes taxes & fees
14 Sept - 15 Sept
7. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
€110
includes taxes & fees
31 Aug - 1 Sept
8. Cozy Corner Motel
Cozy Corner MotelWilliamstown
- Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
€89
includes taxes & fees
9 Sept - 10 Sept
View all properties
Top Cheshire Hotel Reviews
Vacation Village in the Berkshires
10/10 Excellent
"Very quiet despite being larger area than we thought. Staff at check-in helpful as our card had been corrupted .. manually entered info and we were all set! Enjoyed our balcony very much. lot of fun in the pool !"
Hotel Downstreet, an Ascend Collection Hotel
8/10 Good
"We have been coming for the last few years. Generally, 4 or 5 times a year. We love the Berkshires. People vote with their feet. It is a good value. We will be back."
The Yankee Inn
8/10 Good
"Almost two hotels in one. Several structures. One nicely updated, all check-ins, breakfast. Our stay was in an older building… while it was clean there was a musty smell. The room was very dated and the ac was loud… Time to upgrade that building."
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"I liked the balcony overlooking the lake"
Howard Johnson by Wyndham Lenox
8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."