Cheshire Hotels with Swimming Pool
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14 Aug - 16 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.
RM395
RM487 total
includes taxes & fees
7 Sept - 8 Sept
2. The Springs Motel
The Springs MotelNew Ashford
- Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
RM654
RM718 total
includes taxes & fees
10 Aug - 11 Aug
3. The Yankee Inn
The Yankee InnLenox
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
RM652
RM728 total
includes taxes & fees
9 Aug - 10 Aug
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.
RM569
RM636 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.
RM681
RM761 total
includes taxes & fees
16 Aug - 17 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.
RM519
RM580 total
includes taxes & fees
23 Aug - 24 Aug
7. Maple Terrace Motel
Maple Terrace MotelWilliamstown
- Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.
RM528
RM590 total
includes taxes & fees
9 Aug - 10 Aug
8. Cozy Corner Motel
Cozy Corner MotelWilliamstown
- Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
RM386
RM454 total
includes taxes & fees
9 Aug - 10 Aug
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Top Cheshire Hotel Reviews
The Black Swan Lee - Lenox, an Ascend Collection Hotel
8/10 Good
"Nice location, nice breakfast, but no elevator."
Holiday Inn & Suites Pittsfield-Berkshires by IHG
8/10 Good
"Breakfast was delayed but the late arriving staff worked quickly to restore it. Quality of food was excellent"
The Yankee Inn
10/10 Excellent
"Last minute reservations and we will return next year. Room, facilities, breakfast, and pool excellent."
Jiminy Peak Mountain Resort
8/10 Good
"Jiminy Peak is located in an absolutely beatiful location in the Berkshires. And it has fun family-friendly summertime activities. But it could use some sprucing up. The pool liner is a little wrinkly and the hot tub is quite stained near the water line. In addition, our room had a nice 2-foot gouge in the wall seemingly caused by the corner of the armchair beneath it. It seems that could/should have been repaired before out arrival. And the dated counertops and fixtures are showing their age. That said, so am I! On the plus side: the iconic scenery, the friendly helpful staff, and the amenities. All in all, a good value for a family getaway. I would definitely recommend the prolerty overall."
The Red Lion Inn
10/10 Excellent
"Escaped into another world on each floor's hallway-the memorabilia and artwork spoke of an honest, New England history. The atmosphere was perfect for a genuine, original immersion into New England's past and LOVED going up and down the 150yr old elevator! Meals delicious w/excellent service. Only one issue we had: the AC in the room was difficult to adjust and were quite chilled even w/turning the thermostat up to 80 deg!!!!!!!!! as suggested by the front desk. Shall make this a yearly visit!"
Howard Johnson by Wyndham Lenox
10/10 Excellent
"Parking"
Hotel Downstreet, an Ascend Collection Hotel
8/10 Good
"Room was clean and staff was nice. Air conditioner was a little noisy"