Cheshire Hotel with Pool
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Cheshire Hotel with Pool
Tonight
11 Aug - 12 AugTomorrow
12 Aug - 13 AugThis weekend
14 Aug - 16 AugNext weekend
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.
HK$758
HK$933 total
includes taxes & fees
9 Sept - 10 Sept
2. The Springs Motel
The Springs MotelNew Ashford
- Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
HK$1,275
HK$1,399 total
includes taxes & fees
9 Sept - 10 Sept
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.
HK$1,091
HK$1,219 total
includes taxes & fees
9 Sept - 10 Sept
4. The Yankee Inn
The Yankee InnLenox
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
HK$1,294
HK$1,446 total
includes taxes & fees
7 Sept - 8 Sept
5. Berkshire Valley Inn
Berkshire Valley InnWilliamstown
- Splash into mountain adventure with seasonal poolside bliss and continental breakfast.
HK$1,306
HK$1,459 total
includes taxes & fees
19 Aug - 20 Aug
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.
HK$996
HK$1,113 total
includes taxes & fees
2 Sept - 3 Sept
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.
HK$1,648
HK$1,840 total
includes taxes & fees
7 Sept - 8 Sept
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.
HK$812
HK$907 total
includes taxes & fees
19 Aug - 20 Aug
View all properties
Top Cheshire Hotel Reviews
Vacation Village in the Berkshires
8/10 Good
"Beautiful location and pricey, but less expensive than most places in the area. It is spacious with a kitchen that we did not use, the rooms are very dated. You can hear through the walls very well. Didn’t use pool because it was so crowded."
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"