Sheffield Hotel Guide - Hotels with Pool in Sheffield, Massachusetts

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Check availability on Sheffield Hotels with Pool

Tonight
26 Nov - 27 Nov
Tomorrow
27 Nov - 28 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Sheffield Hotels with Pool

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 €127
includes taxes & fees
11 Dec - 12 Dec
Element Lenox Berkshires
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, (1007)
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 hot tub while mountain vistas provide a stunning backdrop for aquatic serenity.
The price is €61
includes taxes & fees
7 Dec - 8 Dec
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 Centre. 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 €92
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
  • Indoor pool
  • Hot tub
9.0 out of 10, Wonderful, (765)
Plunge into the pristine indoor pool after exploring hiking trails or nearby Tanglewood Music Centre. 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
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
  • Outdoor pool
7.6 out of 10, Good, (825)
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 €76
includes taxes & fees
30 Nov - 1 Dec
Howard Johnson by Wyndham Lenox
2 indoor pools, 2 outdoor pools, pool umbrellas, pool loungers
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
South Lee
  • 2 outdoor pools
  • 2 indoor pools
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (790)
Swimming enthusiasts rejoice at this four-pool paradise nestled in the Berkshires. Families appreciate the well-maintained waters complemented by sun loungers, umbrellas, and refreshing poolside drinks, creating memorable mountain getaways year-round.
The price is €115
includes taxes & fees
8 Dec - 9 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (1003)
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 €107
includes taxes & fees
7 Dec - 8 Dec
Hampton Inn & Suites Berkshires-Lenox
Seasonal outdoor pool
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Business services
  • Housekeeping
9.4 out of 10, Exceptional, (159)
Dive into summer bliss at the seasonal outdoor pool, open June through September, after enjoying the complimentary cooked-to-order breakfast. Surrounded by quiet countryside, this bed & breakfast offers fireplace warmth, picnic areas, and attentive service from helpful staff.
The price is €163
includes taxes & fees
27 Nov - 28 Nov
Blackberry River Inn
Indoor pool
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
  • Indoor pool
9.2 out of 10, Wonderful, (657)
Sparkling waters await in the pristine indoor swimming pool, complemented by a modern fitness centre for complete rejuvenation. Nearby Tanglewood Music Centre offers cultural enrichment, while Jae's Asian Fusion restaurant provides delicious dining options.
The price is €107
includes taxes & fees
7 Dec - 8 Dec
Hilton Garden Inn Lenox Pittsfield
Indoor pool
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.2 out of 10, Wonderful, (587)
Sparkling waters welcome swimmers at the inviting indoor pool, complementing days spent exploring nearby Tanglewood Music Centre and Kennedy Park. Staff members earn consistent praise for their attentive service at this comfortable Lenox retreat.
The price is €118
includes taxes & fees
24 Dec - 25 Dec
Courtyard by Marriott Lenox Berkshires
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 Sheffield Hotel Reviews

Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"This hotel was perfect for our one night stay. The room was very clean, bed was comfortable and the shower had good water pressure. The owners were very friendly. They had kuerig coffee available in the lobby, which was perfect to grab a cup of coffee to go."
Jeanne 1-night trip
Posted 5 days ago
Monument Mountain Motel

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Frequently asked questions

What are some accommodation options with pools in Sheffield?
Wilder House Berkshires: Offers free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Features 3 restaurants, an outdoor pool and spa services. Berkshires Untold: Features 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. The Red Lion Inn: Offers a seasonal outdoor pool, an indoor pool and buffet. The Black Swan Lee - Lenox, an Ascend Collection Hotel: Provides buffet, an indoor pool and complimentary high-speed (wired) Internet access.
What is there to see and do in Sheffield?
Spend some time experiencing the great outdoors at Housatonic River. Discover sights such as Magnolia Bluffs Casino, Mount Everett State Reservation and Thom Reed UFO Monument Park during your stay.
When is the best time to book a hotel with a pool in Sheffield?
Taking the local weather in Sheffield into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Sheffield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.