Find Hotels with a Pool in Sheffield, MA

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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.
$135 nightly
The price is $151
Nov 20 - Nov 21
Total with taxes and fees
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.
$102 nightly
The price is $114
Nov 16 - Nov 17
Total with taxes and fees
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.
$100 nightly
The price is $112
Dec 7 - Dec 8
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
  • Outdoor pool
  • Pool loungers
9.4 out of 10, Exceptional, (13)
Mountain adventures begin at the outdoor pool, complete with sun loungers and umbrellas for post-hike relaxation. Sauna sessions, complimentary bicycles, and nearby hiking trails complement the experience at this scenic Berkshire retreat.
$250 nightly
The price is $280
Nov 19 - Nov 20
Total with taxes and fees
Prospect Berkshires
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.
$120 nightly
The price is $135
Nov 16 - Nov 17
Total with taxes and fees
Berkshire Mountain Lodge
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.
$111 nightly
The price is $124
Nov 23 - Nov 24
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
  • Outdoor pool
7.6 out of 10, Good, (820)
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.
$79 nightly
The price is $88
Nov 14 - Nov 15
Total with taxes and fees
Howard Johnson by Wyndham Lenox
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.
$111 nightly
The price is $124
Nov 23 - Nov 24
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
  • Near the beach
7.6 out of 10, Good, (409)
Mountain recreation surrounds this quiet getaway featuring a refreshing seasonal pool open from August. After swimming, guests appreciate clean, comfortable rooms with mini fridges before exploring nearby skiing and hiking trails.
$86 nightly
The price is $97
Dec 2 - Dec 3
Total with taxes and fees
Sunset Inn
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.
$158 nightly
The price is $182
Nov 17 - Nov 18
Total with taxes and fees
Blackberry River 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

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

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.

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