Find Hotels with a Pool in Sheffield, MA

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Check availability on Sheffield Hotels with a Pool

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Sep 27 - Sep 28
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Oct 10 - Oct 12

Top Sheffield Hotels with a Pool

Blackberry River Inn
Seasonal outdoor pool

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (136)
"Loved everything especially Lucas and Joe💟☮️"
$164 nightly
The price is $189
Sep 29 - Sep 30
Total with taxes and fees
Blackberry River Inn
Berkshire Mountain Lodge
Indoor pool

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (661)
"It was a great Stay where we had to it was a good area I would come back to this place again "
$113 nightly
The price is $126
Sep 29 - Sep 30
Total with taxes and fees
Berkshire Mountain Lodge
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (803)
"Great place to stay for overnight stays. Breakfast was appreciated."
$79 nightly
The price is $88
Sep 29 - Sep 30
Total with taxes and fees
Howard Johnson by Wyndham Lenox
The Little Lion
Pool

The Little Lion

3.0 star property
8.6 out of 10, Excellent, (534)
"Comfy, quiet, and clean "
$131 nightly
The price is $147
Oct 29 - Oct 30
Total with taxes and fees
The Little Lion
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (45)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
$127 nightly
The price is $141
Oct 2 - Oct 3
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (738)
"The lodging was convenient to all the area attractions."
$142 nightly
The price is $159
Oct 2 - Oct 3
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (1008)
"Very clean, nice amenities , great location!!"
$149 nightly
The price is $167
Sep 30 - Oct 1
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
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, (665)
"Very Good; Clean, Quiet Motel, Area has many dining options."
$134 nightly
The price is $150
Sep 30 - Oct 1
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
The Yankee, Trademark Collection by Wyndham
Indoor pool, seasonal outdoor pool, sun loungers

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1012)
"Nice area to visit "
$116 nightly
The price is $130
Oct 1 - Oct 2
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Apple Tree Inn
Seasonal outdoor pool

Apple Tree Inn

3.0 star property
8.6 out of 10, Excellent, (307)
"Very clean room and comfortable bed. Friendly staff and restaurant/bar on site. "
$184 nightly
The price is $206
Sep 29 - Sep 30
Total with taxes and fees
Apple Tree 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.
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Top Sheffield Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"It's just a nice place and the staff is very nice "
Robin 5-night trip
Posted 3 days ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

What are some accommodations with pools in Sheffield?
Wilder House Berkshires: Provides free self parking, an indoor pool, and complimentary wireless internet access. Guesthouse Cabin vacation rentals in Berkshire County: Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Berkshire Mountain Lodge: Offers 3 restaurants, an outdoor pool, and spa services. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Provides free self parking, an outdoor pool, and complimentary wireless internet access. The Red Lion Inn: Offers a seasonal outdoor pool, an indoor pool, and buffet.
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.

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