Hotels with Pool & Resorts in Sheffield from NZ$153

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Check availability on Sheffield Hotels with Pool

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Best Sheffield Hotels with Pool

Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is NZ$254
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
9.2 out of 10, Wonderful, (1000)
"Great stay!"
United States
Ann
The price is NZ$173
includes taxes & fees
11 Dec - 12 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
9.2 out of 10, Wonderful, (64)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is NZ$177
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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
9.0 out of 10, Wonderful, (795)
"Place was great!"
United States
Benjamin
The price is NZ$240
includes taxes & fees
10 Dec - 11 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is NZ$370
includes taxes & fees
5 Jan - 6 Jan 2026
The Red Lion Inn
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (778)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
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
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is NZ$200
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn & Suites Berkshires-Lenox
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (410)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is NZ$169
includes taxes & fees
8 Dec - 9 Dec
Sunset Inn
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (827)
"Staff was very friendly and helpful."
United States
Pamela
The price is NZ$153
includes taxes & fees
7 Dec - 8 Dec
Howard Johnson by Wyndham Lenox
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

3.0 star property
Great Barrington
8.6 out of 10, Excellent, (547)
"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
The price is NZ$213
includes taxes & fees
1 Jan - 2 Jan 2026
The Little Lion
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

The Ponds at Foxhollow

The Ponds at Foxhollow

10/10 Excellent
"There was a coffee machine but no filters nor beans. I wish they had been provided."
art 3-night trip
Posted 3 days ago
The Ponds at Foxhollow

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Frequently asked questions

What are some accommodation options with pools in Sheffield?
Wilder House Berkshires: Provides free self parking, an indoor pool and complimentary wireless Internet access. Antique Farmhouse Totally Restored: Features 3 restaurants, an outdoor pool and spa services. Berkshire Mountain Lodge: Offers 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. The Red Lion Inn: Features a seasonal outdoor pool, an indoor pool and buffet. Berkshires Untold: Offers 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, Three Mile Pond Wildlife Management Area and Mount Everett State Reservation 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.