Search Hotels with Pool in Sheffield

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Sheffield Hotels with Pool

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 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 Rp2.266.245
Rp2.531.396 total
includes taxes & fees
4 Jan - 5 Jan 2026
Element Lenox Berkshires
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, (1007)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is Rp1.555.316
Rp1.737.288 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 Rp1.897.770
Rp2.119.809 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (795)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is Rp1.656.626
Rp2.225.474 total
includes taxes & fees
11 Jan - 12 Jan 2026
Berkshire Mountain Lodge
Property grounds
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
United States
Lori
The price is Rp2.518.050
Rp3.562.705 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 Rp2.145.443
Rp2.396.427 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 Rp1.745.848
Rp1.950.111 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Berkshires-Lenox
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, (15)
"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 Rp4.901.804
Rp6.037.780 total
includes taxes & fees
8 Jan - 9 Jan 2026
Prospect 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 Rp1.326.173
Rp1.481.285 total
includes taxes & fees
25 Dec - 26 Dec
Howard Johnson by Wyndham Lenox
Exterior
The Little Lion

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 Rp1.846.570
Rp2.062.619 total
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.
View all properties

Top Sheffield Hotel Reviews

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.