Sheffield Hotels with Pools - Outdoor/Indoor Pools in Sheffield MA

Sheffield hotels and motels with swimming pools that are perfect for a family are listed below. Search for cheap and discount hotel rates at hotels with a pool in or near Sheffield, MA for your upcoming individual or family vacation. We list the best pool equipped, kid friendly Sheffield Massachusetts hotel and motel rooms for children. Review the list of Sheffield hotels with indoor or outdoor pools below to find the perfect lodging for you and your kids.

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Sheffield Hotels with Outdoor or Indoor Pools

Race Brook Lodge
+1-888-389-4121

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864 South Undermountain Rd, Sheffield, MA 01257
  • Has swimming pool: Outdoor seasonal pool. The seasonal pool will be open from May 01 to October 01.
  • Two-star hotel
  • Check-in: 3:00 PM - 11:00 PM
More Photos Pool image of Race Brook Lodge
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Very Good 4.2 /5 Hotel Reviews Call BookMore Details
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Fairfield Inn & Suites by Marriott Great Barrington Lenox / Berkshires
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
249 Stockbridge Rd, Great Barrington, MA 01230 ~6.70 miles north of Sheffield
  • Pool available: Wheelchair-accessible pool.
  • 3-star hotel
  • 93 sleeping rooms in hotel
More Photos Pool image of Fairfield Inn & Suites by Marriott Great Barrington Lenox / Berkshires
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Very Good 4.7 /5 Guest Reviews Call BookMore Details
Lantern House Motel
+1-800-716-8490

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256 Stockbridge Road, Great Barrington, MA 01230 ~6.77 miles north of Sheffield
  • Pool available: Outdoor seasonal pool. The seasonal pool will be open from June to September. Pool access available from 9:00 AM to 7:00 PM.
  • Midscale Motel property
  • 14 sleeping rooms in hotel
More Photos Swimming pool at Lantern House Motel
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Very Good 4.1 /5 Review Score Call BookMore Details
Holiday Inn Express Hotel & Suites Great Barrington by IHG
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
415 Stockbridge Rd, Great Barrington, MA 01230 ~7.09 miles north of Sheffield
  • Pool details: Pool hoist on site.
  • Mid-scale property
  • Gym is available on property
More Photos Pool image of Holiday Inn Express Hotel & Suites Great Barrington by IHG
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Very Good 4.4 /5 Recent Reviews Call BookMore Details
Prospect Berkshires
+1-888-965-1860

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50 Prospect Lake Rd, Egremont, MA 01230 ~7.46 miles northwest of Sheffield
  • Pool available: Pool umbrellas, Wheelchair-accessible pool, Pool sun loungers, Fence around pool. Pool access available from 6:00 AM to 10:00 PM.
  • 3 star hotel
  • Check in: 4:00 PM - 8:00 PM
More Photos Photo of Prospect Berkshires Pool
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Excellent 5.0 /5 Review Score Call BookMore Details
Little Cat Lodge
+1-888-788-5576

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37 Catamount Rd, Copake Falls, NY 12529 ~7.53 miles northwest of Sheffield
  • Pool available: Outdoor seasonal pool. The seasonal pool will be open from June 15 to September 07.
  • Two-star property
  • Hotel has 14 rooms
More Photos Swimming pool at Little Cat Lodge
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Very Good 4.9 /5 Review Score Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires
+1-888-897-9207

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400 Stockbridge Rd, Great Barrington, MA 01230 ~8.26 miles north of Sheffield
  • Pool in hotel
  • 2-star Motel hotel
  • Check-in: 2:00 PM - midnight
More Photos Pool image of Travelodge by Wyndham Great Barrington Berkshires
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Average 3.7 /5 Latest Reviews Call BookMore Details
The Red Lion Inn
+1-888-311-4278

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30 Main Street, Stockbridge, MA 01262 ~12.05 miles north of Sheffield
  • Has swimming pool: Pool sun loungers.
  • Mid-scale property
  • Pets are Welcome
More Photos Swimming pool at The Red Lion Inn
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Very Good 4.4 /5 Read Reviews Call BookMore Details
Holiday Inn Club Vacations Oak n Spruce Resort
+1-888-469-4795

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190 Meadow Street, South Lee, MA 01260 ~12.11 miles north of Sheffield
  • Has swimming pool: Pool umbrellas, Billiards or pool table, Outdoor seasonal pool, Pool sun loungers, Fence around pool. The seasonal pool will be open from May to September. Pool access available from 8:00 AM to 10:00 PM.
  • Three Star hotel
  • 334 rooms in hotel
More Photos Photo of Holiday Inn Club Vacations Oak n Spruce Resort Pool
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Very Good 4.6 /5 Review Score Call BookMore Details
Interlaken Inn & Resort
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
74 Interlaken Road, Lakeville, CT 06039 ~12.22 miles southwest of Sheffield
  • Pool available: Billiards or pool table, Outdoor seasonal pool. The seasonal pool will be open from May to September.
  • Three Star property
  • Check in: 4:00 PM - 11:30 PM
More Photos Photo of Interlaken Inn & Resort Pool
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Very Good 4.1 /5 Guest Reviews Call BookMore Details
Sunset Inn
+1-888-841-5292

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150 Housatonic Street, Lee, MA 01238 ~14.37 miles northeast of Sheffield
  • Pool in hotel: Outdoor seasonal pool. The seasonal pool will be open from June 23 to September 02. Pool access available from 10:00 AM to 8:00 PM.
  • 2 star Motel hotel
  • 2 floors in property
More Photos Pool image of Sunset Inn
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Average 3.8 /5 Latest Reviews Call BookMore Details
Wheatleigh
+1-888-455-5160

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11 Hawthorne Road, Lenox, MA 01240 ~16.15 miles north of Sheffield
  • Has swimming pool
  • Luxury 5 star property
  • Free breakfast
More Photos Pool image of Wheatleigh
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Average 3.5 /5 Hotel Reviews Call BookMore Details
Canyon Ranch Lenox
+1-888-965-8297

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165 Kemble St, Lenox, MA 01240 ~16.92 miles north of Sheffield
  • We have a pool
  • Two star Resort property
  • Check-in time: 3:00 PM
More Photos Pool image of Canyon Ranch Lenox
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Very Good 4.0 /5 Recent Reviews Call BookMore Details
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Berkshire Travelodge
+1-888-906-6358

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12703 Rte 22, Austerlitz, NY 12029 ~17.14 miles north of Sheffield
  • We have a pool ready for use
  • Midscale Motel property
  • Pets are OK
More Photos Swimming pool at Berkshire Travelodge
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Poor 2.7 /5 Latest Reviews Call BookMore Details
Hampton Terrace Inn
+1-888-749-6785

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91 Walker Street, Lenox, MA 01240 ~17.29 miles north of Sheffield
  • Pool available: Outdoor seasonal pool, Fence around pool. The seasonal pool will be open from May to September.
  • Four star hotel
  • 2 floors in hotel
More Photos Photo of Hampton Terrace Inn Pool
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Very Good 4.5 /5 Review Score Call BookMore Details
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Courtyard by Marriott Lenox Berkshires
+1-888-878-9982

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70 Pittsfield Rd, Lenox, MA 01240 ~18.91 miles north of Sheffield
  • Pool in hotel: Pool hoist on site, Wheelchair-accessible pool.
  • 3 star property
  • 4 floors in hotel
More Photos Pool image of Courtyard by Marriott Lenox Berkshires
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Very Good 4.6 /5 Recent Reviews Call BookMore Details
Element by Marriott Lenox Berkshires
+1-888-389-4485

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130 PITTSFIELD ROAD, Lenox, MA 01240 ~19.16 miles north of Sheffield
  • Pool in hotel: Pool hoist on site.
  • Midscale property
  • 3 floors in property
More Photos Photo of Element by Marriott Lenox Berkshires Pool
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Very Good 4.8 /5 Review Score Call BookMore Details
Troutbeck
+1-888-389-4121

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515 Leedsville Rd, Amenia, NY 12501 ~19.53 miles southwest of Sheffield
  • Includes a pool: Wheelchair-accessible pool, Billiards or pool table.
  • Luxurious 5-star hotel
  • Pets Welcome
More Photos Swimming pool at Troutbeck
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Excellent 5.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
445 Pittsfield Rd, Lenox, MA 01240 ~20.55 miles north of Sheffield
  • Pool available: Pool hoist on site, Wheelchair-accessible pool, Pool sun loungers. Pool access available from 8:00 AM to 10:00 PM.
  • Mid-scale property
  • Fitness + Health Center
More Photos Pool image of Hampton Inn & Suites Berkshires-Lenox
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Very Good 4.5 /5 Recent Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox
+1-800-716-8490

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462 Pittsfield Rd, Lenox, MA 01240 ~20.67 miles north of Sheffield
  • Has swimming pool
  • Two-star Motel hotel
  • 2 floors in hotel
More Photos Swimming pool at Howard Johnson by Wyndham Lenox
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Average 3.8 /5 Recent Reviews Call BookMore Details
The Yankee Inn
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
461 Pittsfield Rd, Lenox, MA 01240 ~20.70 miles north of Sheffield
  • Includes a pool: Outdoor seasonal pool, Pool sun loungers, Fence around pool. The seasonal pool will be open from June to September. Pool access available from 8:00 AM to 10:00 PM.
  • Three Star property
  • Check-in time: 3:00 PM - anytime
More Photos Photo of The Yankee Inn Pool
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Very Good 4.6 /5 Read Reviews Call BookMore Details
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
+1-888-965-1860

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1055 South Street, Pittsfield, MA 01201 ~21.02 miles north of Sheffield
  • Pool details: Pool hoist on site, Wheelchair-accessible pool. Pool access available from 8:00 AM to 10:00 PM.
  • Three Star property
  • Free comp. breakfast
More Photos Swimming pool at Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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Very Good 4.7 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield
+1-888-788-5576

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1032 South Street, Pittsfield, MA 01201 ~21.05 miles north of Sheffield
  • Pool details: Swimming pool, Wheelchair-accessible pool.
  • Three Star hotel
  • Pet Friendly
More Photos Pool image of Hilton Garden Inn Lenox Pittsfield
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Very Good 4.6 /5 Reviews Call BookMore Details
Berkshire Inn
+1-888-897-9207

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150 West Housatonic St, Pittsfield, MA 01201 ~23.45 miles north of Sheffield
  • Pool in hotel: Outdoor seasonal pool. The seasonal pool will be open from June to August.
  • Low Cost Motel hotel
  • Check in time: 2:00 PM - 1:00 AM
More Photos Pool image of Berkshire Inn
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Average 3.9 /5 Guest Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires by IHG
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
One West Street, Pittsfield, MA 01201 ~23.85 miles north of Sheffield
  • Includes a pool: Pool access available from 7:00 AM to 9:00 PM.
  • 3-star hotel
  • Fitness center on property
More Photos Swimming pool at Holiday Inn & Suites Pittsfield-Berkshires by IHG
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Average 3.9 /5 Latest Reviews Call BookMore Details
Pocketbook Hotel and Bath
+1-888-469-4795

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549 Washington Street, Hudson, NY 12534 ~23.89 miles west of Sheffield
  • Pool in hotel: Pool access available from 9:00 AM to 9:00 PM.
  • property
  • Hotel has 46 rooms
More Photos Photo of Pocketbook Hotel and Bath Pool
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Very Good 4.3 /5 Recent Reviews Call BookMore Details
The Amelia
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
339 Allen St, Hudson, NY 12534 ~24.36 miles west of Sheffield
  • Pool available: Pool umbrellas, Outdoor seasonal pool, Pool sun loungers, Fence around pool. The seasonal pool will be open from May 18 to October 02.
  • Inexpensive property
  • Check in: 3:00 PM - anytime
More Photos Photo of The Amelia Pool
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Very Good 4.9 /5 Latest Reviews Call BookMore Details
Belden House & Mews
+1-888-841-5292

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31 North Street, Litchfield, CT 06759 ~26.42 miles south of Sheffield
  • Pool available: Wheelchair-accessible pool, Outdoor seasonal pool. The seasonal pool will be open from May to September.
  • Luxury 5 star hotel
  • Check in: 4:00 PM - anytime
More Photos Swimming pool at Belden House & Mews
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Very Good 4.5 /5 Recent Reviews Call BookMore Details
The Litchfield Inn
+1-888-455-5160

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432 Bantam Road, Litchfield, 06759 ~26.73 miles south of Sheffield
  • Pool details: Outdoor seasonal pool. The seasonal pool will be open from June 13 to October 31.
  • High end property
  • 15 suites in hotel
More Photos Pool image of The Litchfield Inn
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Very Good 4.6 /5 Review Score Call BookMore Details
Disney Magic at Jiminy Mountain
+1-888-965-8297

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37 Corey Rd. 712, Hancock, MA01237 ~30.90 miles north of Sheffield
  • We have a pool
  • Four star hotel
  • Check in: 16:00:00 - 00:00:00
More Photos Swimming pool at Disney Magic at Jiminy Mountain
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Average 3.9 /5 Review Score Call BookMore Details
Club Wyndham Bentley Brook
+1-888-906-6358

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1 Corey Road, Lanesboro, MA 01237 ~31.05 miles north of Sheffield
  • Includes a pool
  • 3 star Resort property
  • Hotel has 152 suites
More Photos Photo of Club Wyndham Bentley Brook Pool
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Very Good 4.5 /5 Review Score Call BookMore Details
Jiminy Peak Mountain Resort
+1-888-749-6785

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37 Corey Rd, Hancock, MA 01237 ~31.06 miles north of Sheffield
  • Pool available: Pool umbrellas, Wheelchair-accessible pool, Pool sun loungers, Fence around pool. Pool access available from 8:00 AM to 10:00 PM.
  • Three Star hotel
  • Check in time: 4:00 PM - midnight
More Photos Swimming pool at Jiminy Peak Mountain Resort
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Very Good 4.1 /5 Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
+1-888-878-9982

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12740 State Route 9 W, West Coxsackie, NY 12192 ~31.09 miles northwest of Sheffield
  • Pool in hotel
  • Mid-scale property
  • Hotel has 3 floors
More Photos Swimming pool at Holiday Inn Express Hotel & Suites West Coxsackie by IHG
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Very Good 4.2 /5 Recent Reviews Call BookMore Details
Willow Pond Motel
+1-888-389-4485

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14 Mountain Turnpike Rd, Catskill, NY 12414 ~31.70 miles west of Sheffield
  • We have a pool ready for use
  • Low Cost Motel property
  • Check in time: 3:00 PM - anytime
More Photos Pool image of Willow Pond Motel
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Very Good 4.6 /5 Recent Reviews Call BookMore Details
Comfort Inn Saugerties
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
2790 Route 32, Saugerties, NY 12477 ~31.76 miles west of Sheffield
  • Has swimming pool: Pool access available from 7 AM to 10 PM.
  • Three Star hotel
  • 2 floors in property
More Photos Pool image of Comfort Inn Saugerties
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Average 3.6 /5 Reviews Call BookMore Details
Howard Johnson by Wyndham Saugerties
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
2764 Route 32, Saugerties, NY 12477 ~31.81 miles west of Sheffield
  • Has swimming pool: Pool access available from 9:00 AM to 9:00 PM.
  • Low Cost hotel
  • Has environment-friendly policy Read more
More Photos Swimming pool at Howard Johnson by Wyndham Saugerties
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Average 3.7 /5 Guest Reviews Call BookMore Details
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
2777 ROUTE 32, Saugerties, NY 12477 ~31.83 miles west of Sheffield
  • We have a pool ready for use
  • Three Star hotel
  • Has environment-friendly policy See policy
More Photos Swimming pool at Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
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Very Good 4.4 /5 Read Reviews Call BookMore Details
Hampton Inn Westfield
+1-800-805-5223

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39 Southampton Rd, Westfield, MA 01085 ~32.23 miles east of Sheffield
  • Pool available: Wheelchair-accessible pool. Pool access available from 9:00 AM to 10:00 PM.
  • 3-star property
  • Hotel has 86 rooms
More Photos Pool image of Hampton Inn Westfield
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Very Good 4.2 /5 Review Score Call BookMore Details
Red Ranch Motel
+1-888-965-1860

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4555 Route 32, Catskill, NY 124146623 ~32.78 miles west of Sheffield
  • Pool in hotel: Billiards or pool table, Pool umbrellas, Outdoor seasonal pool, Children's pool, Pool sun loungers. The seasonal pool will be open from June to August. Pool access available from 10 AM to 8 PM.
  • Mid-scale Motel property
  • Check in time: 3:00 PM - anytime
More Photos Pool image of Red Ranch Motel
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Average 3.6 /5 Recent Reviews Call BookMore Details
Simsbury Inn
+1-888-788-5576

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397 Hopmeadow Street, Weatogue, CT 06070 ~33.09 miles southeast of Sheffield
  • Pool details: Billiards or pool table, Pool sun loungers.
  • Mid-scale property
  • Hotel has 7 suites
More Photos Pool image of Simsbury Inn
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Very Good 4.3 /5 Guest Reviews Call BookMore Details
Four Seasons Motel
+1-888-897-9207

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5063 NY 32, Catskill, NY 12414 ~33.29 miles west of Sheffield
  • Has swimming pool: Outdoor seasonal pool. The seasonal pool will be open from May 23 to September 12. Pool access available from 10:30 AM to 8:00 PM.
  • Inexpensive Motel hotel
  • Check in time: 2:00 PM - 10:00 PM
More Photos Pool image of Four Seasons Motel
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Very Good 4.2 /5 Hotel Reviews Call BookMore Details
Mayflower Inn & Spa Auberge Collection
+1-888-311-4278

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118 Woodbury Rd., Washington, CT 06793 ~33.33 miles south of Sheffield
  • Pool in hotel: Outdoor seasonal pool. The seasonal pool will be open from May to October.
  • Luxurious Five Star hotel
  • Airport shuttle provided
More Photos Pool image of Mayflower Inn & Spa Auberge Collection
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Very Good 4.7 /5 Review Score Call BookMore Details
Residence Inn by Marriott Kingston
+1-888-469-4795

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800 Frank Sottile Boulevard, Kingston, NY 12401 ~33.72 miles west of Sheffield
  • Has swimming pool: Wheelchair-accessible pool.
  • Mid-scale hotel
  • Pets are OK
More Photos Pool image of Residence Inn by Marriott Kingston
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Very Good 4.5 /5 Latest Reviews Call BookMore Details
The Springs Motel
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
94 U.S. 7, New Ashford, MA 01237 ~33.75 miles north of Sheffield
  • Pool in hotel: Outdoor seasonal pool. The seasonal pool will be open from June to September.
  • 2-star Motel hotel
  • 20 sleeping rooms in hotel
More Photos Swimming pool at The Springs Motel
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Courtyard by Marriott Kingston
+1-888-841-5292

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500 Frank Sottile Blvd, Kingston, NY 12401 ~33.87 miles west of Sheffield
  • Pool details: Wheelchair-accessible pool.
  • Three Star property
  • Hotel has a green policy Learn more
More Photos Pool image of Courtyard by Marriott Kingston
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Very Good 4.4 /5 Review Score Call BookMore Details
Residence Inn by Marriott Hartford Avon
+1-888-455-5160

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55 Simsbury Rd, Avon, CT 06001 ~33.95 miles southeast of Sheffield
  • Includes a pool: Pool umbrellas, Wheelchair-accessible pool, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from May to September.
  • 3-star property
  • 100 suites in hotel
More Photos Swimming pool at Residence Inn by Marriott Hartford Avon
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Very Good 4.4 /5 Latest Reviews Call BookMore Details
Hampton Inn Kingston
+1-888-965-8297

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1307 Ulster Ave, Kingston, NY 12401 ~34.07 miles west of Sheffield
  • Pool details: Pool sun loungers.
  • 3-star hotel
  • Pets/Animals Allowed
More Photos Photo of Hampton Inn Kingston Pool
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Very Good 4.5 /5 Read Reviews Call BookMore Details
Berkshire Valley Inn
+1-888-906-6358

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2541 Hancock Rd, Williamstown, MA 01267 ~34.20 miles north of Sheffield
  • Pool in hotel: Outdoor seasonal pool. The seasonal pool will be open from September 10 to May 11. Pool access available from 8:00 AM to 8:00 PM.
  • 3 star property
  • Hotel has 16 rooms
More Photos Pool image of Berkshire Valley Inn
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Very Good 4.6 /5 Read Reviews Call BookMore Details
Avon Old Farms Hotel
+1-888-749-6785

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279 Avon Mountain Rd, Avon, CT 06001 ~34.82 miles southeast of Sheffield
  • Pool details: Billiards or pool table, Outdoor seasonal pool.
  • Three Star property
  • Check in time: 3:00 PM - anytime
More Photos Pool image of Avon Old Farms Hotel
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Very Good 4.2 /5 Read Reviews Call BookMore Details
Riedlbauers Resort
+1-888-878-9982

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
57 Ravine Dr., Round Top, NY 12473 ~35.73 miles west of Sheffield
  • Pool available: Pool umbrellas, Pool sun loungers.
  • Midscale hotel
  • Check in time: 12:00 PM - 5:00 PM
More Photos Swimming pool at Riedlbauers Resort
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