Lakeville Hotels with Pools - Outdoor/Indoor Pools in Lakeville CT

Lakeville 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 Lakeville, CT for your upcoming individual or family vacation. We list the best pool equipped, kid friendly Lakeville Connecticut hotel and motel rooms for children. Review the list of Lakeville hotels with indoor or outdoor pools below to find the perfect lodging for you and your kids.
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Lakeville Hotels with Outdoor or Indoor Pools

Interlaken Inn & Resort 74 Interlaken Road, Lakeville, CT 06039 +1-888-389-4121
  • Pool details: Billiards or pool table, Outdoor seasonal pool. The seasonal pool will be open from May to September.
  • Three Star hotel
  • Fitness center on property
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Very Good 8.2 /10 Latest Reviews Call BookMore Details
Troutbeck 515 Leedsville Rd, Amenia, NY 12501 +1-888-675-2083 ~8.00 miles southwest of Lakeville
  • Has swimming pool: Wheelchair-accessible pool, Billiards or pool table.
  • Luxurious Five Star hotel
  • Pets/Dogs Allowed
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Excellent 10.0 /10 Reviews Call BookMore Details
Race Brook Lodge 864 South Undermountain Rd, Sheffield, MA 01257 +1-800-716-8490 ~9.40 miles north of Lakeville
  • Includes a pool: Outdoor seasonal pool. The seasonal pool will be open from May 01 to October 01.
  • 2-star hotel
  • Hotel has 29 rooms
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Very Good 8.4 /10 Review Score Call BookMore Details
Little Cat Lodge 37 Catamount Rd, Copake Falls, NY 12529 +1-800-805-5223 ~15.63 miles north of Lakeville
  • Pool in hotel: Outdoor seasonal pool. The seasonal pool will be open from June 15 to September 07.
  • Economical property
  • Check in: 4:00 PM - 9:00 PM
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Excellent 9.8 /10 Read Reviews Call BookMore Details
Prospect Berkshires 50 Prospect Lake Rd, Egremont, MA 01230 +1-888-965-1860 ~17.00 miles north of Lakeville
  • Pool in hotel: Pool umbrellas, Wheelchair-accessible pool, Pool sun loungers, Fence around pool. Pool access available from 6:00 AM to 10:00 PM.
  • Midscale property
  • Check in: 4:00 PM - 8:00 PM
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Excellent 10.0 /10 Guest Reviews Call BookMore Details
The Litchfield Inn 432 Bantam Road, Litchfield, CT 06759 +1-888-788-5576 ~18.12 miles southeast of Lakeville
  • Includes a pool: Outdoor seasonal pool. The seasonal pool will be open from June 13 to October 31.
  • 4-star property
  • Gym / Fitness Center Available
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Excellent 9.2 /10 Guest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox / Berkshires 249 Stockbridge Rd, Great Barrington, MA 01230 +1-888-897-9207 ~18.33 miles north of Lakeville
  • Pool details: Wheelchair-accessible pool.
  • Affordable hotel
  • Free breakfast
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Excellent 9.4 /10 Guest Reviews Call BookMore Details
Belden House & Mews 31 North Street, Litchfield, CT 06759 +1-888-311-4278 ~18.35 miles southeast of Lakeville
  • Pool details: Wheelchair-accessible pool, Outdoor seasonal pool. The seasonal pool will be open from May to September.
  • Luxurious 5-star hotel
  • Fitness / Gym is on-site
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Excellent 9.0 /10 Review Score Call BookMore Details
Lantern House Motel 256 Stockbridge Road, Great Barrington, MA 01230 +1-888-469-4795 ~18.39 miles north of Lakeville
  • Pool details: Outdoor seasonal pool. The seasonal pool will be open from June to September. Pool access available from 9:00 AM to 7:00 PM.
  • 2-star Motel property
  • 14 rooms in hotel
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Holiday Inn Express Hotel & Suites Great Barrington by IHG 415 Stockbridge Rd, Great Barrington, MA 01230 +1-888-734-9421 ~18.72 miles north of Lakeville
  • Pool details: Pool hoist on site.
  • Mid-scale property
  • Check in time: 3:00 PM - 3:30 AM
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Very Good 8.8 /10 Latest Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires 400 Stockbridge Rd, Great Barrington, MA 01230 +1-888-841-5292 ~19.89 miles north of Lakeville
  • Includes a pool
  • Low-priced Motel property
  • Free breakfast
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Average 7.4 /10 Latest Reviews Call BookMore Details
Mayflower Inn & Spa Auberge Collection 118 Woodbury Rd., Washington, CT 06793 +1-888-455-5160 ~22.88 miles south of Lakeville
  • Pool details: Outdoor seasonal pool. The seasonal pool will be open from May to October.
  • Luxurious Five Star property
  • Airport shuttle provided
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Excellent 9.4 /10 Recent Reviews Call BookMore Details
The Red Lion Inn 30 Main Street, Stockbridge, MA 01262 +1-888-965-8297 ~23.75 miles north of Lakeville
  • Pool details: Pool sun loungers.
  • Midscale hotel
  • Check in time: 4:00 PM - anytime
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Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires 190 Meadow Street, South Lee, MA 01260 +1-888-906-6358 ~23.85 miles north of Lakeville
  • 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.
  • 3-star hotel
  • Has environment-friendly policy See more
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Sunset Inn 150 Housatonic Street, Lee, MA 01238 +1-888-749-6785 ~26.08 miles north of Lakeville
  • Pool details: 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 property
  • 27 rooms in hotel
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Average 7.6 /10 Read Reviews Call BookMore Details
Pocketbook Hotel and Bath 549 Washington Street, Hudson, NY 12534 +1-888-878-9982 ~27.74 miles northwest of Lakeville
  • Pool available: Pool access available from 9:00 AM to 9:00 PM.
  • hotel
  • Check in time: 3:00 PM - midnight
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Very Good 8.6 /10 Recent Reviews Call BookMore Details
Wheatleigh 11 Hawthorne Road, Lenox, MA 01240 +1-888-389-4485 ~27.83 miles north of Lakeville
  • Has swimming pool
  • Luxury 5 star hotel
  • 19 rooms in hotel
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Average 7.0 /10 Reviews Call BookMore Details
Berkshire Travelodge 12703 Rte 22, Austerlitz, NY 12029 +1-888-389-4121 ~27.97 miles north of Lakeville
  • With a pool!
  • Midscale Motel property
  • 25 sleeping rooms in hotel
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Poor 5.4 /10 Guest Reviews Call BookMore Details
The Amelia 339 Allen St, Hudson, NY 12534 +1-888-675-2083 ~28.08 miles northwest of Lakeville
  • Includes a pool: Pool umbrellas, Outdoor seasonal pool, Pool sun loungers, Fence around pool. The seasonal pool will be open from May 18 to October 02.
  • Economical property
  • 8 rooms in property
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Excellent 9.6 /10 Guest Reviews Call BookMore Details
Cranwell Spa and Golf Resort 55 Lee Road, Lenox, MA 01240 +1-800-716-8490 ~28.38 miles north of Lakeville
  • Has a pool!
  • 3-star Resort property
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Canyon Ranch Lenox 165 Kemble St, Lenox, MA 01240 +1-800-805-5223 ~28.64 miles north of Lakeville
  • Pool in hotel
  • Three Star Resort hotel
  • Hotel has 24 suites
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Very Good 8.0 /10 Review Score Call BookMore Details
Residence Inn by Marriott Kingston 800 Frank Sottile Boulevard, Kingston, NY 12401 +1-888-965-1860 ~28.79 miles west of Lakeville
  • Pool in hotel: Wheelchair-accessible pool.
  • Midscale hotel
  • 92 rooms in hotel
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Excellent 9.0 /10 Guest Reviews Call BookMore Details
Courtyard by Marriott Kingston 500 Frank Sottile Blvd, Kingston, NY 12401 +1-888-788-5576 ~28.94 miles west of Lakeville
  • Includes a pool: Wheelchair-accessible pool.
  • Midscale property
  • Hotel has an eco-friendly policy See more
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Very Good 8.8 /10 Review Score Call BookMore Details
Hampton Terrace Inn 91 Walker Street, Lenox, MA 01240 +1-888-897-9207 ~29.01 miles north of Lakeville
  • Has swimming pool: Outdoor seasonal pool, Fence around pool. The seasonal pool will be open from May to September.
  • High end property
  • Hotel has 14 rooms
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Excellent 9.0 /10 Recent Reviews Call BookMore Details
Hampton Inn Kingston 1307 Ulster Ave, Kingston, NY 12401 +1-888-311-4278 ~29.16 miles west of Lakeville
  • Pool available: Pool sun loungers.
  • 3 star hotel
  • Check in: 3:00 PM - 2:00 AM
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Very Good 8.7 /10 Review Score Call BookMore Details
Comfort Inn Saugerties 2790 Route 32, Saugerties, NY 12477 +1-888-469-4795 ~29.82 miles west of Lakeville
  • Pool in hotel: Pool access available from 7 AM to 10 PM.
  • Affordable hotel
  • Free complimentary breakfast
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Average 7.2 /10 Guest Reviews Call BookMore Details
Howard Johnson by Wyndham Saugerties 2764 Route 32, Saugerties, NY 12477 +1-888-734-9421 ~29.83 miles west of Lakeville
  • Has swimming pool: Pool access available from 9:00 AM to 9:00 PM.
  • Low Cost property
  • 83 sleeping rooms in hotel
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Average 7.4 /10 Reviews Call BookMore Details
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG 2777 ROUTE 32, Saugerties, NY 12477 +1-888-841-5292 ~29.86 miles west of Lakeville
  • Has a pool!
  • Midscale property
  • Has environment-friendly policy See policy
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Very Good 8.8 /10 Recent Reviews Call BookMore Details
Quality Inn Poughkeepsie 536 Haight Ave. Building A, Poughkeepsie, NY 12603 +1-888-455-5160 ~30.02 miles southwest of Lakeville
  • Our hotel comes with a pool
  • Mid-scale hotel
  • Gym / Fitness Center Available
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Average 7.6 /10 Hotel Reviews Call BookMore Details
Rodeway Inn Poughkeepsie 536 Haight Ave. Building B, Poughkeepsie, NY 12603 +1-888-965-8297 ~30.03 miles southwest of Lakeville
  • Includes a pool
  • Low-priced property
  • 10 sleeping rooms in hotel
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Poor 5.8 /10 Review Score Call BookMore Details
Courtyard by Marriott Lenox Berkshires 70 Pittsfield Rd, Lenox, MA 01240 +1-888-906-6358 ~30.62 miles north of Lakeville
  • Includes a pool: Pool hoist on site, Wheelchair-accessible pool.
  • 3-star property
  • Check-in: 3:00 PM - 2:00 AM
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Excellent 9.2 /10 Latest Reviews Call BookMore Details
Element by Marriott Lenox Berkshires 130 PITTSFIELD ROAD, Lenox, MA 01240 +1-888-749-6785 ~30.87 miles north of Lakeville
  • Pool in hotel: Pool hoist on site.
  • Affordable hotel
  • Hotel has 3 floors
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Excellent 9.6 /10 Latest Reviews Call BookMore Details
Kingston Regency Inn 503 Washington Avenue, Kingston, NY 12401 +1-888-878-9982 ~31.02 miles west of Lakeville
  • Has swimming pool: Pool hoist on site, Wheelchair-accessible pool, Billiards or pool table. Pool access available from 10:00 AM to 10:00 PM.
  • 3-star property
  • Check in time: 3:00 PM - anytime
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Average 7.4 /10 Reviews Call BookMore Details
Holiday Inn Express Poughkeepsie by IHG 2750 South Road, Poughkeepsie, NY 12601 +1-888-389-4485 ~31.98 miles southwest of Lakeville
  • Has swimming pool: Wheelchair-accessible pool.
  • 3-star hotel
  • Comp. Breakfast
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Very Good 8.4 /10 Read Reviews Call BookMore Details
Residence Inn by Marriott Hartford Avon 55 Simsbury Rd, Avon, CT 06001 +1-888-389-4121 ~32.02 miles east of Lakeville
  • 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
  • Has environment-friendly policy Read more
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Very Good 8.8 /10 Review Score Call BookMore Details
Simsbury Inn 397 Hopmeadow Street, Weatogue, CT 06070 +1-888-675-2083 ~32.18 miles east of Lakeville
  • Includes a pool: Billiards or pool table, Pool sun loungers.
  • 3-star hotel
  • Pets Welcome
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Hampton Inn & Suites Berkshires-Lenox 445 Pittsfield Rd, Lenox, MA 01240 +1-800-716-8490 ~32.26 miles north of Lakeville
  • Pool available: Pool hoist on site, Wheelchair-accessible pool, Pool sun loungers. Pool access available from 8:00 AM to 10:00 PM.
  • Affordable property
  • 24 suites in property
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Excellent 9.0 /10 Review Score Call BookMore Details
Howard Johnson by Wyndham Lenox 462 Pittsfield Rd, Lenox, MA 01240 +1-800-805-5223 ~32.39 miles north of Lakeville
  • With a pool!
  • 2 star Motel hotel
  • Complimentary breakfast is offered
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Average 7.6 /10 Latest Reviews Call BookMore Details
The Yankee Inn 461 Pittsfield Rd, Lenox, MA 01240 +1-888-965-1860 ~32.41 miles north of Lakeville
  • Pool in hotel: 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.
  • 3-star hotel
  • 96 sleeping rooms in hotel
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Very Good 8.5 /10 Review Score Call BookMore Details
Home2 Suites by Hilton Poughkeepsie 2619 South Road, Poughkeepsie, NY 12601 +1-888-788-5576 ~32.50 miles southwest of Lakeville
  • Pool available: Pool hoist on site, Wheelchair-accessible pool.
  • 3-star hotel
  • 111 rooms in hotel
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Very Good 8.9 /10 Review Score Call BookMore Details
Willow Pond Motel 14 Mountain Turnpike Rd, Catskill, NY 12414 +1-888-897-9207 ~32.60 miles northwest of Lakeville
  • We have a pool
  • Two star Motel hotel
  • Check in: 3:00 PM - anytime
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Very Good 8.9 /10 Hotel Reviews Call BookMore Details
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG 1055 South Street, Pittsfield, MA 01201 +1-888-311-4278 ~32.74 miles north of Lakeville
  • Pool available: Pool hoist on site, Wheelchair-accessible pool. Pool access available from 8:00 AM to 10:00 PM.
  • 3-star property
  • 81 rooms in hotel
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Excellent 9.4 /10 Guest Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield 1032 South Street, Pittsfield, MA 01201 +1-888-469-4795 ~32.77 miles north of Lakeville
  • Pool in hotel: Swimming pool, Wheelchair-accessible pool.
  • Three Star hotel
  • Hotel has 95 rooms
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Excellent 9.2 /10 Recent Reviews Call BookMore Details
Residence Inn by Marriott Poughkeepsie 2525 South Rd, Poughkeepsie, NY 12601 +1-888-734-9421 ~32.84 miles southwest of Lakeville
  • Has swimming pool: Wheelchair-accessible pool.
  • Three Star hotel
  • Pets Welcome
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Avon Old Farms Hotel 279 Avon Mountain Rd, Avon, CT 06001 +1-888-841-5292 ~32.87 miles east of Lakeville
  • Includes a pool: Billiards or pool table, Outdoor seasonal pool.
  • Midscale property
  • Pets/Animals Allowed
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Homewood Suites by Hilton Poughkeepsie 900 Thomas Watson Dr, Poughkeepsie, NY 12601 +1-888-455-5160 ~32.94 miles southwest of Lakeville
  • Includes a pool: Pool hoist on site, Wheelchair-accessible pool. Pool access available from 7:00 AM to 10:00 PM.
  • Midscale property
  • Pets Welcome
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Red Ranch Motel 4555 Route 32, Catskill, NY 124146623 +1-888-965-8297 ~33.17 miles northwest of Lakeville
  • 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.
  • Midscale Motel hotel
  • Check in time: 3:00 PM - anytime
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Average 7.2 /10 Latest Reviews Call BookMore Details
Hampton Inn & Suites Poughkeepsie 2361 South Rd, Poughkeepsie, NY 12601 +1-888-906-6358 ~33.18 miles southwest of Lakeville
  • Pool details: Wheelchair-accessible pool.
  • 3-star hotel
  • 129 rooms in property
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Excellent 9.2 /10 Recent Reviews Call BookMore Details
Hampton Inn Waterbury 777 Chase Pkwy, Waterbury, CT 06708 +1-888-749-6785 ~33.22 miles southeast of Lakeville
  • Pool in hotel: Wheelchair-accessible pool.
  • Mid-scale property
  • Free comp. breakfast
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Very Good 8.2 /10 Latest Reviews Call BookMore Details
Holiday Inn Poughkeepsie by IHG 2170 South Rd, Poughkeepsie, NY 12601 +1-888-878-9982 ~33.24 miles southwest of Lakeville
  • Pool available: Wheelchair-accessible pool.
  • Affordable hotel
  • 149 rooms in hotel
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