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

Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.6 out of 10, Exceptional, (10)
Swimming enthusiasts appreciate the serene indoor pool that provides year-round aquatic enjoyment regardless of weather. After energizing laps, guests gather at the outdoor firepit or enjoy a complimentary manager's reception before retreating to individually furnished rooms.
The price is AED 496
AED 554 total
includes taxes & fees
23 Nov - 24 Nov
Element Lenox Berkshires
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
  • Indoor pool
8.8 out of 10, Excellent, (692)
Splash into the warm, pristine indoor pool after exploring nearby hiking trails or skiing at Butternut. Modern rooms with premium bedding await, while a complimentary breakfast buffet energizes adventures in Great Barrington's vibrant surroundings.
The price is AED 375
AED 418 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool, seasonal outdoor pool, sun loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Indoor pool
  • Pool loungers
  • Hot tub
9.2 out of 10, Wonderful, (1000)
Shimmering waters beckon at dual pool options, where indoor relaxation meets seasonal outdoor splendor. After exploring nearby Bousquet Ski Area, guests unwind in the rejuvenating hot tub while mountain vistas provide a stunning backdrop for aquatic serenity.
The price is AED 367
AED 410 total
includes taxes & fees
7 Dec - 8 Dec
The Yankee, Trademark Collection by Wyndham
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
  • Indoor pool
  • Hot tub
9.0 out of 10, Wonderful, (753)
Plunge into the pristine indoor pool after exploring hiking trails or nearby Tanglewood Music Center. Sun loungers invite relaxation while the hot tub soothes tired muscles. Beyond aquatic pleasures, this lodge offers fitness facilities and an arcade room.
Berkshire Mountain Lodge
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
  • Outdoor pool
7.6 out of 10, Good, (821)
Sparkling waters beckon at the inviting outdoor pool, a refreshing retreat after exploring nearby Tanglewood Music Center. Deep soaking bathtubs and hydromassage showers in clean, spacious rooms complement this conveniently located getaway.
The price is AED 290
AED 324 total
includes taxes & fees
16 Nov - 17 Nov
Howard Johnson by Wyndham Lenox
Indoor pool
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
  • Indoor pool
9.2 out of 10, Wonderful, (656)
Sparkling waters await in the pristine indoor swimming pool, complemented by a modern fitness center for complete rejuvenation. Nearby Tanglewood Music Center offers cultural enrichment, while Jae's Asian Fusion restaurant provides delicious dining options.
The price is AED 408
AED 456 total
includes taxes & fees
23 Nov - 24 Nov
Hilton Garden Inn Lenox Pittsfield
Seasonal outdoor pool
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Business services
  • Housekeeping
9.4 out of 10, Exceptional, (157)
Dive into summer bliss at the seasonal outdoor pool, open June through September, after enjoying the complimentary cooked-to-order breakfast. Surrounded by quiet countryside, this bed & breakfast offers fireplace warmth, picnic areas, and attentive service from helpful staff.
The price is AED 592
AED 680 total
includes taxes & fees
19 Nov - 20 Nov
Blackberry River Inn
Indoor pool
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.2 out of 10, Wonderful, (586)
Sparkling waters welcome swimmers at the inviting indoor pool, complementing days spent exploring nearby Tanglewood Music Center and Kennedy Park. Staff members earn consistent praise for their attentive service at this comfortable Lenox retreat.
The price is AED 433
AED 484 total
includes taxes & fees
14 Dec - 15 Dec
Courtyard by Marriott Lenox Berkshires
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
Lenox
  • Indoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (1001)
Splash into vacation mode at the indoor pool where comfortable loungers await after exhilarating outdoor adventures. This art deco haven balances active pursuits with relaxation, offering fitness facilities and a delicious free breakfast buffet to fuel Berkshire explorations.
The price is AED 408
AED 456 total
includes taxes & fees
23 Nov - 24 Nov
Hampton Inn & Suites Berkshires-Lenox
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
  • Outdoor pool
  • Pool loungers
8.8 out of 10, Excellent, (1001)
Sparkling waters invite refreshment at the outdoor pool, complemented by a rejuvenating hot tub that remains open year-round. Beyond aquatic pleasures, this historic hotel enchants with excellent dining, tasteful accommodations, and friendly service.
The price is AED 549
AED 777 total
includes taxes & fees
17 Nov - 18 Nov
The Red Lion 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

Top Sheffield Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Early check in."
Colleen 1-night trip
Posted 4 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations with pools in Sheffield?
Wilder House Berkshires: Offers free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Offers 3 restaurants, an outdoor pool, and spa services. Berkshires Untold: Offers a seasonal outdoor pool, an indoor pool, and buffet. The Black Swan Lee - Lenox, an Ascend Collection Hotel: Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli. The Red Lion Inn: Features 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, Mount Everett State Reservation, and Thom Reed UFO Monument Park 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.