Find Hotels with a Pool in Sheffield, MA

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 a Pool

Top Sheffield Hotels with a Pool

Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (448)
"The motel seems to be managed and cleaned by the owners. Not the ritz, but clean and a bargain compared with other lodging in the area. The owner was very responsive. "
The price is NT$2,058
NT$2,305 total
includes taxes & fees
Oct 16 - Oct 17
Berkshire Travel Lodge
Berkshire Mountain Lodge
Indoor pool

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (685)
"Great stay, perfect "
The price is NT$2,346
NT$3,304 total
includes taxes & fees
Nov 2 - Nov 3
Berkshire Mountain Lodge
Blackberry River Inn
Seasonal outdoor pool

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (142)
"Loved everything especially Lucas and Joe💟☮️"
The price is NT$5,012
NT$5,764 total
includes taxes & fees
Oct 14 - Oct 15
Blackberry River Inn
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (805)
"Great place to stay for overnight stays. Breakfast was appreciated."
The price is NT$2,409
NT$2,691 total
includes taxes & fees
Oct 20 - Oct 21
Howard Johnson by Wyndham Lenox
Element Lenox Berkshires
Indoor pool

Element Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (5)
"New hotel very nice"
The price is NT$4,127
NT$4,610 total
includes taxes & fees
Nov 9 - Nov 10
Element Lenox Berkshires
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (669)
"Very comfortable and safe."
The price is NT$3,277
NT$3,660 total
includes taxes & fees
Nov 3 - Nov 4
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Little Cat Lodge
Seasonal outdoor pool

Little Cat Lodge

2.0 star property
9.4 out of 10, Exceptional, (60)
"Atmosphere, service and food was excellent. Definitely going back!"
Little Cat Lodge
Hampton Inn & Suites Berkshires-Lenox
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Very clean, nice amenities , great location!!"
The price is NT$3,888
NT$4,343 total
includes taxes & fees
Nov 2 - Nov 3
Hampton Inn & Suites Berkshires-Lenox
The Little Lion
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

The Little Lion

3.0 star property
8.6 out of 10, Excellent, (534)
"Comfy, quiet, and clean "
The price is NT$3,943
NT$4,405 total
includes taxes & fees
Nov 2 - Nov 3
The Little Lion
Courtyard by Marriott Lenox Berkshires
Indoor pool

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (576)
"The front desk, food service, and housekeeping staff were all very friendly. The room was immaculate as well. "
The price is NT$3,882
NT$4,336 total
includes taxes & fees
Nov 9 - Nov 10
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.
View all properties

Top Sheffield Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"Staff was very friendly. Room was ok, but the bathroom tub, floor, and walls needed more attention. Microwave and fridge in room. Perfect location for taking in shows at the beautiful Mahaiwe theatre, as well as browsing Main St shoppes and restaurants. Close driving distance to area attractions."
Petri 2-night trip
Posted 2 days ago
Quality Inn

Explore a world of travel with Expedia

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. Berkshire Mountain Lodge: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Offers 3 restaurants, an outdoor pool, and spa services. Berkshires Untold: Features a seasonal outdoor pool, an indoor pool, and buffet. The Red Lion Inn: Offers buffet, an indoor pool, and complimentary 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 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.