Find Hotels with a Pool in Sheffield, MA

  • 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 a Pool

Our top choices for Sheffield hotels with a pool

Indoor pool

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (19 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is AED 511
AED 570 total
includes taxes & fees
1 Mar - 2 Mar
Element Lenox Berkshires
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (834 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
The price is AED 253
AED 283 total
includes taxes & fees
22 Feb - 23 Feb
Howard Johnson by Wyndham Lenox
Indoor pool, seasonal outdoor pool, sun loungers

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is AED 340
AED 380 total
includes taxes & fees
1 Mar - 2 Mar
The Yankee, Trademark Collection by Wyndham
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (553 reviews)
"Great friendly staff"
United States
Pablo
The price is AED 404
AED 451 total
includes taxes & fees
22 Feb - 23 Feb
The Little Lion
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (847 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is AED 419
AED 550 total
includes taxes & fees
22 Feb - 23 Feb
Berkshire Mountain Lodge
Indoor pool

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (735 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is AED 379
AED 423 total
includes taxes & fees
22 Feb - 23 Feb
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Seasonal outdoor pool

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (168 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is AED 566
AED 651 total
includes taxes & fees
22 Feb - 23 Feb
Blackberry River Inn
Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,001 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is AED 503
AED 726 total
includes taxes & fees
23 Feb - 24 Feb
The Red Lion Inn
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (19 reviews)
"Excellent local stay - would recommend to all"
United States
Gentian
The price is AED 720
AED 927 total
includes taxes & fees
24 Feb - 25 Feb
Prospect Berkshires
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
"owners was nice, room was clean"
United States
tom
The price is AED 342
AED 382 total
includes taxes & fees
21 Feb - 22 Feb
Sunset 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.
View all properties

Choose what matters most at hotels with a pool in Sheffield

Breakfast included
4 stars

Eid al-Fitr Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now

Top Sheffield Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Beautiful room with a fireplace. "
Carolyn 2-night trip
Posted 10 hours ago
The Yankee, Trademark Collection by Wyndham

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations with pools in Sheffield?
Wilder House Berkshires: Features free self parking, an indoor pool, and complimentary wireless internet access. Antique Farmhouse Totally Restored: Offers a seasonal outdoor pool, an indoor pool, and buffet. Guesthouse Cabin vacation rentals in Berkshire County: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Berkshire Mountain Lodge: Features 3 restaurants, an outdoor pool, and spa services. The Yankee, Trademark Collection by Wyndham: Features a sauna, an outdoor pool, and spa services.
What is there to see and do in Sheffield?
Spend some time experiencing the great outdoors at Housatonic River. Discover sights such as Lime Kiln Farm Wildlife Sanctuary, Magnolia Bluffs Casino, and Drury Preserve during your stay.
When is the best time to book a hotel with a pool in Sheffield?
Taking into account the local weather in Sheffield can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.