Hotels with Pool & Resorts in Cheshire from NZ$153

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Check availability on Cheshire Hotels with Pool

Best Cheshire Hotels with 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 NZ$178
includes taxes & fees
29 Nov - 30 Nov
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 energising laps, guests gather at the outdoor firepit or enjoy a complimentary manager's reception before retreating to individually furnished rooms.
The price is NZ$261
includes taxes & fees
22 Dec - 23 Dec
Element Lenox Berkshires
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 Centre. Deep soaking bathtubs and hydromassage showers in clean, spacious rooms complement this conveniently located getaway.
The price is NZ$157
includes taxes & fees
24 Nov - 25 Nov
Howard Johnson by Wyndham Lenox
Indoor pool, seasonal outdoor pool, pool 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 splendour. After exploring nearby Bousquet Ski Area, guests unwind in the rejuvenating spa pool while mountain vistas provide a stunning backdrop for aquatic serenity.
The price is NZ$153
includes taxes & fees
4 Dec - 5 Dec
The Yankee, Trademark Collection by Wyndham
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
  • Outdoor pool
  • Indoor pool
  • Pool umbrellas
8.8 out of 10, Excellent, (2138)
Mountain-view relaxation awaits at the indoor and outdoor pools after exploring Berkshire trails. Families appreciate the children's pool, playground, and game room, while skiers love the direct access to Jiminy Peak slopes.
The price is NZ$167
includes taxes & fees
25 Nov - 26 Nov
Vacation Village in the Berkshires
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
Lenox
  • Indoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (1000)
Splash into holiday mode at the indoor pool where comfortable loungers await after exhilarating outdoor adventures. This art deco haven balances active pursuits with relaxation, offering fitness facilities and a delicious free breakfast buffet to fuel Berkshire explorations.
The price is NZ$221
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn & Suites Berkshires-Lenox
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 NZ$212
includes taxes & fees
25 Nov - 26 Nov
The Springs Motel
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 Centre. Soothing spa pool sessions complement winter activities like cross-country skiing, while attentive staff ensure a refreshingly clean, well-maintained aquatic retreat.
The price is NZ$198
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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 NZ$171
includes taxes & fees
2 Dec - 3 Dec
Sunset Inn
Outdoor pool
Brook Farm Inn

Brook Farm Inn

3.5 star property
Lenox
  • Outdoor pool
  • Poolside bar
9.4 out of 10, Exceptional, (162)
Poolside cocktails enhance summer swims at this tranquil Berkshires retreat. Guests savour exceptional made-to-order breakfasts before relaxing in spacious, fireplace-equipped rooms. Nearby Tanglewood and hiking trails complete perfect seasonal getaways.
Brook Farm Inn
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

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"All the design elements are wonderful! I enjoyed the room and the beautiful view of the town and the mountains. So clean and so spacious!! The staff - not so much, but everything else great."
Susie 2-night trip
Posted 23 hours ago
Hotel Downstreet, an Ascend Collection Hotel

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Frequently asked questions

What are some accommodation options 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 high-speed (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 the local weather in Cheshire into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm of snowfall.