Search Hotels with Pool in Sheffield

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Check availability on Sheffield Hotels with Pool

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Sheffield hotels with a pool

Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is ฿4,195
฿4,686 total
includes taxes & fees
4 Jan - 5 Jan 2026
Element Lenox Berkshires
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is ฿2,455
฿2,742 total
includes taxes & fees
26 Dec - 27 Dec
Howard Johnson by Wyndham Lenox
Indoor pool, seasonal outdoor pool, pool loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is ฿2,879
฿3,216 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Yankee, Trademark Collection by Wyndham
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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, (68)
"Extremely impressed by this hotel. The staff was very friendly and professional. The rooms were so comfortable and high quality everything! Check in and check out was easy. Highly recommend!"
United States
Jeanne
The price is ฿3,513
฿3,924 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Seasonal outdoor pool
Sunset Inn

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 ฿2,797
฿3,124 total
includes taxes & fees
26 Dec - 27 Dec
Sunset Inn
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"Old time charm and hot tub under the stars"
United States
Lori
The price is ฿4,662
฿6,595 total
includes taxes & fees
14 Jan - 15 Jan 2026
The Red Lion Inn
Indoor pool
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is ฿3,974
฿4,439 total
includes taxes & fees
3 Jan - 4 Jan 2026
Hilton Garden Inn Lenox Pittsfield
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers
Hampton Inn & Suites Berkshires-Lenox

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 ฿3,207
฿3,582 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Berkshires-Lenox
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (548)
"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 ฿3,418
฿3,818 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Little Lion
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, pool loungers
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (16)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is ฿9,074
฿11,177 total
includes taxes & fees
8 Jan - 9 Jan 2026
Prospect 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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Yes"
Richard 3-night trip
Posted 6 days ago
The Red Lion Inn
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 weeks ago
The Ponds at Foxhollow

Frequently asked questions

What are some accommodation options with pools in Sheffield?
Wilder House Berkshires: Provides a seasonal outdoor pool, an indoor pool and buffet. The Yankee, Trademark Collection by Wyndham: Features free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Offers 3 restaurants, an outdoor pool and spa services. The Red Lion Inn: Offers 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. Berkshires Untold: Provides a snack bar/deli, an indoor pool and buffet.
What is there to see and do in Sheffield?
Surround yourself with nature at Housatonic River and Thom Reed UFO Monument Park. Discover sights such as Magnolia Bluffs Casino, Three Mile Pond Wildlife Management Area and Ashley House 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.