Find Hotels with a Pool in Cheshire, MA
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21 Aug - 23 AugOur 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.
AED 355
AED 437 total
includes taxes & fees
2 Sep - 3 Sep
2. The Springs Motel
The Springs MotelNew Ashford
- Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
AED 589
AED 646 total
includes taxes & fees
25 Aug - 26 Aug
3. 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.
AED 511
AED 571 total
includes taxes & fees
10 Sep - 11 Sep
4. Berkshire Valley Inn
Berkshire Valley InnWilliamstown
- Splash into mountain adventure with seasonal poolside bliss and continental breakfast.
AED 582
AED 650 total
includes taxes & fees
13 Aug - 14 Aug
5. The Yankee Inn
The Yankee InnLenox
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
AED 606
AED 677 total
includes taxes & fees
7 Sep - 8 Sep
6. 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.
AED 466
AED 521 total
includes taxes & fees
2 Sep - 3 Sep
7. Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott WilliamstownWilliamstown
- Swim indoors year-round at this welcoming retreat with an indoor pool, hot tub, and extended pool hours for ultimate relaxation.
AED 771
AED 862 total
includes taxes & fees
7 Sep - 8 Sep
8. 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.
AED 380
AED 425 total
includes taxes & fees
7 Sep - 8 Sep
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Top Cheshire Hotel Reviews
The Red Lion Inn
10/10 Excellent
"This is an old inn. It’s elegant, fun and very comfortable. Lots of dark, antique furniture and communal card games. The staff is friendly and some have been there many years. Many of the guests return year after year. If that’s what you’re looking for, you will love it. I do. If you are looking for sleek and spotless, you are best suited elsewhere."
The Yankee Inn
8/10 Good
"The room was clean. Linens in good shape. Good access to lots of activities nearby. Breakfast can be crowded. Go early."
Jiminy Peak Mountain Resort
10/10 Excellent
"Quiet and serene. Great weekend escape!"
Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
"Hotel is currently under renovation which impacted parking and only 1 elevator available. Hotel staff, cleanliness and location excellent."
The Black Swan Lee - Lenox, an Ascend Collection Hotel
8/10 Good
"For a non-chain hotel, I was pleasantly surprised. Clean and comfortable. But definitely a B- C+ place which was perfect for a quick stay."
Howard Johnson by Wyndham Lenox
10/10 Excellent
"Parking"