Hotels with Swimming Pool in Cheshire, Massachusetts

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Check availability on Cheshire Hotels with Swimming Pool

Top Cheshire Hotels with Swimming Pool

Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
  • Indoor pool
8.0 out of 10, Very Good, (962)
Swimmers splash in the pristine indoor pool from 7 AM to 9 PM, complemented by an on-site health club for complete wellness. Hiking trails and skiing opportunities nearby make this centrally located hotel an ideal family-friendly retreat.
The price is P5,197
P5,805 total
includes taxes & fees
Nov 21 - Nov 22
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.8 out of 10, Exceptional, (11)
Swimming enthusiasts appreciate the serene indoor pool that provides year-round aquatic enjoyment regardless of weather. After energizing laps, guests gather at the outdoor firepit or enjoy a complimentary manager's reception before retreating to individually furnished rooms.
The price is P7,728
P8,633 total
includes taxes & fees
Dec 11 - Dec 12
Element Lenox Berkshires
Indoor pool, seasonal outdoor pool, sun loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Indoor pool
  • Pool loungers
  • Hot tub
9.2 out of 10, Wonderful, (1005)
Shimmering waters beckon at dual pool options, where indoor relaxation meets seasonal outdoor splendor. After exploring nearby Bousquet Ski Area, guests unwind in the rejuvenating hot tub while mountain vistas provide a stunning backdrop for aquatic serenity.
The price is P5,516
P6,161 total
includes taxes & fees
Dec 7 - Dec 8
The Yankee, Trademark Collection by Wyndham
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
  • Indoor pool
  • Hot tub
9.4 out of 10, Exceptional, (60)
Plunge into the indoor pool open from 8:00 AM to 10:00 PM after exploring nearby Tanglewood Music Center. Soothing hot tub sessions complement winter activities like cross-country skiing, while attentive staff ensure a refreshingly clean, well-maintained aquatic retreat.
The price is P6,218
P6,946 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
  • Breakfast included
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Business services
9.2 out of 10, Wonderful, (882)
Families splash in the lazy river while adventure seekers prepare for nearby hiking trails and cross-country skiing. This family-run motel balances aquatic fun with mountain recreation, creating perfect days that end with sunset barbecues in the garden.
The price is P4,407
P5,202 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Corner Motel
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
  • Near the beach
7.6 out of 10, Good, (410)
Mountain recreation surrounds this quiet getaway featuring a refreshing seasonal pool open from August. After swimming, guests appreciate clean, comfortable rooms with mini fridges before exploring nearby skiing and hiking trails.
The price is P5,310
P5,931 total
includes taxes & fees
Dec 2 - Dec 3
Sunset Inn
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers
Maple Terrace Motel

Maple Terrace Motel

2.5 star property
Williamstown
  • Pool loungers
9.6 out of 10, Exceptional, (584)
Pristine waters of the seasonal outdoor pool beckon guests with comfortable loungers and umbrellas. Family-owned hospitality shines through immaculate gardens and picnic areas, creating a refreshing retreat near The Clark Art Institute.
The price is P5,841
P6,524 total
includes taxes & fees
Nov 24 - Nov 25
Maple Terrace Motel
Seasonal outdoor pool
The Springs Motel

The Springs Motel

2.0 star property
New Ashford
  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Microwave
9.2 out of 10, Wonderful, (87)
Surrounded by mountain views, the seasonal outdoor pool offers summer relaxation with comfortable lounge chairs and hangout spots. Guests love the well-appointed rooms, friendly staff, and outdoor entertainment areas featuring firepits and charcoal grills.
The price is P6,413
P7,035 total
includes taxes & fees
Nov 21 - Nov 22
The Springs Motel
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
  • Outdoor pool
7.6 out of 10, Good, (824)
Sparkling waters beckon at the inviting outdoor pool, a refreshing retreat after exploring nearby Tanglewood Music Center. Deep soaking bathtubs and hydromassage showers in clean, spacious rooms complement this conveniently located getaway.
The price is P4,655
P5,200 total
includes taxes & fees
Dec 19 - Dec 20
Howard Johnson by Wyndham Lenox
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
  • Indoor pool
  • Hot tub
9.0 out of 10, Wonderful, (761)
Plunge into the pristine indoor pool after exploring hiking trails or nearby Tanglewood Music Center. Sun loungers invite relaxation while the hot tub soothes tired muscles. Beyond aquatic pleasures, this lodge offers fitness facilities and an arcade room.
Berkshire Mountain Lodge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cheshire Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Great stay!"
Ann 1-night trip
Posted 5 days ago
The Yankee, Trademark Collection by Wyndham

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Frequently asked questions

What are some accommodations with pools in Cheshire?
Harbour House Inn: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. Vacation Village in the Berkshires: Provides free self parking, an indoor pool, and complimentary wireless internet access. Hotel Downstreet, an Ascend Collection Hotel: Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Offers a health club, an indoor pool, and complimentary wired internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Features 3 restaurants, an outdoor pool, and spa services.
What is there to see and do in Cheshire?
Take in the natural beauty with a stop at Mount Greylock State Reservation. Discover sights such as St Mary's of the Assumption Church, Mount Greylock State Reservation Visitor Center, and Mount Greylock during your stay.
When is the best time to book a hotel with a pool in Cheshire?
Taking into account the local weather in Cheshire is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.