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

Chesterfield 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 Chesterfield, MA for your upcoming individual or family vacation. We list the best pool equipped, kid friendly Chesterfield Massachusetts hotel and motel rooms for children. Review the list of Chesterfield hotels with indoor or outdoor pools below to find the perfect lodging for you and your kids.

Chesterfield Hotels with Outdoor or Indoor Pools

Hampton Inn Hadley Amherst Area 24 Bay Rd., Hadley, MA 01035 Call ~12.62 miles east of Chesterfield
  • Pool details: Indoor Heated Pool open from 7am - 9pm daily. Located on the first floor just off the lobby.
  • Affordable Suburban hotel
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From$109
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Towneplace Suites by Marriott - Hadley 237 Russell St., Hadley, MA 01035 Call ~14.02 miles east of Chesterfield
  • Pool details: Heated Indoor Pool open from 7am - 9pm daily.
  • 3-star Suburban hotel
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From$140
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Courtyard by Marriott Hadley Amherst 423 Russell St., Hadley, MA 01035 Call ~15.43 miles east of Chesterfield
  • Includes a pool: 6AM-11PM Indoor Pool & Spa
  • 3-star Downtown property
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From$109
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Fairfield Inn & Suites Springfield Holyoke in Holyoke 229 Whiting Farms Rd., Holyoke, MA 01040 Call ~18.05 miles southeast of Chesterfield
  • Has swimming pool: Indoor and heated pool open from 6AM to 10PM
  • Three Star Suburban hotel
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From$109
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Hampton Inn Chicopee / Springfield - Chicopee 600 Memorial Dr., Chicopee, MA 01020 Call ~20.13 miles southeast of Chesterfield
  • Includes a pool: Relax in our Indoor Pool open 9 AM - 10 PM.
  • Midscale Suburban property
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From$109
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Residence Inn by Marriott Springfield Chicopee in Chicopee 500 Memorial Dr., Chicopee, MA 01020 Call ~20.25 miles southeast of Chesterfield
  • Includes a pool: Indoor pool Pool Hours 9am to 10pm
  • Affordable Highway hotel
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From$99
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TRU by Hilton Chicopee Springfield in Chicopee 440 Memorial Dr., Chicopee, MA 01020 Call ~20.29 miles southeast of Chesterfield
  • Pool details: Indoor Pool. Open 7AM-10PM daily.
  • 3-star property
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From$90
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Residence Inn by Marriott West Springfield 64 Border Way, West Springfield, MA 01089 Call ~20.55 miles southeast of Chesterfield
  • Pool in hotel: Indoor pool open from 6am-12am daily
  • Affordable Highway property
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From$97
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Comfort Inn & Suites 106 Capital Dr., West Springfield, MA 01089 Call ~20.81 miles southeast of Chesterfield
  • Has swimming pool: Indoor pool and whirlpool open daily from 7am-10pm
  • 2 star Suburban property
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From$129
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Quality Inn West Springfield 1150 Riverdale St., West Springfield, MA 01089 Call ~20.86 miles southeast of Chesterfield
  • Includes a pool: Covered seasonal outdoor pool Handicapped lift open 10am to 10pm
  • Low Cost Suburban property
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From$75
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Courtyard West Spring Marriott 885 Riverdale St., West Springfield, MA 01089 Call ~21.27 miles southeast of Chesterfield
  • With a pool!
  • 3 star hotel
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From$90
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Holiday Inn Express Pittsfield Lenox Berkshires 1055 South St., Pittsfield, MA 01201 Call ~21.56 miles west of Chesterfield
  • Includes a pool: Indoor heated pool & hot tub, hours: 8am - 10pm, Deep end: 5 feet
  • Three Star Suburban hotel
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From$80
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Berkshire Mountain Lodge 8 Dan Fox Dr., Pittsfield, MA 01201 Call ~21.64 miles west of Chesterfield
  • Has swimming pool: Indoor pool & hot tub Open daily 8am-11pm
  • Inexpensive Mountain property
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From$125
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Hilton Garden Inn Lenox Pittsfield : 1032 South St. 1032 South St., Pittsfield, MA 01201 Call ~21.71 miles west of Chesterfield
  • Has swimming pool: Indoor heated pool/hot tub
  • Midscale Suburban property
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From$95
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Best Western Springfield West Inn 429 Riverdale St., West Springfield, MA 01089 Call ~21.92 miles southeast of Chesterfield
  • Has swimming pool
  • 3 star property
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From$73
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The Black Swan Lee Lenox An Ascend Collection Hotel : 435 Laurel St. 435 Laurel St., Lee, MA 01238 Call ~21.92 miles west of Chesterfield
  • We have a pool ready for use
  • 3-star Lake property
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From$65
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La Quinta by Wyndham in Springfield 100 Congress St., Springfield, MA 01104 Call ~23.19 miles southeast of Chesterfield
  • Pool in hotel: Heated indoor pool open daily 7am - 9pm. Located just off the lobby on the first floor next to the small arcade.
  • 3 star Downtown hotel
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From$80
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Holiday Inn Club Vacations Oak N Spruce Resort - South Lee 190 Meadow St., South Lee, MA 01260 Call ~23.58 miles west of Chesterfield
  • Pool available: Two outdoor pools (seasonal) Two indoor pools (hours vary) Hot Tub (hours vary)
  • Three Star Mountain property
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From$89
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Sheraton Springfield Monarch Place Hotel : 1 Monarch Place 1 Monarch Place, Springfield, MA 01144 Call ~23.72 miles southeast of Chesterfield
  • Pool in hotel: We have an indoor pool with an outdoor patio area. Weekday Hours: 5:30am-10pm Saturday Hours: 8am-10pm Sunday Hours: 8am-8pm
  • Three Star Downtown hotel
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From$80
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Holiday Inn Express Springfield Downtown in Springfield 145 State St., Springfield, MA 01103 Call ~23.87 miles southeast of Chesterfield
  • Pool available: Indoor heated pool
  • Midscale property
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From$80
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Holiday Inn Express Ludlow by IHG 321 Center St., Ludlow, MA 01056 Call ~24.05 miles southeast of Chesterfield
  • Has swimming pool: Heated indoor pool open 7am - 9pm daily.
  • Mid-scale Highway hotel
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From$89
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Vacation Village in The Berkshires 276 Brodie Mtn Rd., Lanesborough, MA 01237 Call ~24.55 miles west of Chesterfield
  • Pool in hotel: Pool hours 8am - 11pm Vacation Village in the Berkshires has a heated indoor swimming pool inside the clubhouse and a heated outdoor swimming pool located behind the clubhouse. Weather permitting, the outdoor pool is open seasonally from Memorial Day through Labor Day. Poolside lounge chairs are available to our owners and guests on a first-come, first-served basis. Pool towels are provided at each pool.
  • 3 star Mountain hotel
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From$75
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Hotel Downstreet Ascend Hotel Collection : 40 Main St. 40 Main St., North Adams, MA 01247 Call ~25.37 miles northwest of Chesterfield
  • Includes a pool: 5am-10pm Indoor
  • Three Star Downtown hotel
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From$136
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The Porches Inn at Mass Moca : 231 River St. 231 River St., North Adams, MA 01247 Call ~25.56 miles northwest of Chesterfield
  • Pool in hotel: Outdoor heated pool open 24 hours daily year round. Sauna, outdoor hot tub and 24 hour fitness Center onsite.
  • 4-star Downtown hotel
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From$199
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Jiminy Peak Mountain Resort - Hancock 37 Corey Rd., Hancock, MA 01237 Call ~25.75 miles west of Chesterfield
  • Pool details: Country Inn Pool is open 8a - 10p daily. Outdoor heated pool open year round.
  • Affordable Mountain hotel
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From$105
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Maple Terrace Motel - Williamstown 555 Main St., Williamstown, MA 01267 Call ~28.26 miles northwest of Chesterfield
  • Has swimming pool: Beautiful secluded heated pool with amazing and breathtaking views. Opens Daily 9 AM and closes at Dusk.
  • Cheap Rural property
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From$59
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Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi - Great Barrington 249 Stockbridge Rd., Great Barrington, MA 01230 Call ~28.81 miles west of Chesterfield
  • Has swimming pool
  • Three Star Resort property
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From$109
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Hilton Garden Inn : Hartford North / Bradley Intl Airport Hartford North / Bradley Intl Airport, Babc2af01bf25d1094cea9b5604bcbb1, CT 06095 Call ~32.24 miles south of Chesterfield
  • Includes a pool: 5:00am- 10:00pm
  • Three Star Airport hotel
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From$80
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The White House Inn in Wilmington 178 Vt 9 East, Wilmington, VT 05363 Call ~32.59 miles north of Chesterfield
  • Includes a pool: Small, shallow indoor pool, open 24 hours a day
  • High end Mountain hotel
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From$75
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Holiday Inn Express & Suites Bradley Airport by IHG in Windsor Locks 600 Spring St., Windsor Locks, CT 06096 Call ~32.83 miles south of Chesterfield
  • Has swimming pool: Indoor Heated Pool open from 7am - 8pm daily. approximately 12 feet x 15 feet.
  • Affordable Airport property
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From$85
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Springhill Suites Marriott Airport in Windsor Locks 225 Ella Grasso Turnpike, Windsor Locks, CT 06096 Call ~32.98 miles south of Chesterfield
  • Pool available: Small indoor heated pool. Not big enough for large groups of people.
  • Three Star Airport property
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From$95
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Econo Lodge Inn & Suites Windsor Locks Bradley Airport 34 Old County Rd., Windsor Locks, CT 06096 Call ~33.28 miles south of Chesterfield
  • Pool in hotel: Seasonal-Outdoor
  • Cheap Airport property
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From$45
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Econo Lodge Brattleboro South 515 Canal St., Brattleboro, VT 05301 Call ~33.78 miles northeast of Chesterfield
  • Includes a swimming pool
  • Low priced Downtown property
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From$53
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Courtyard By Marriott Hartford/Windsor Airport 1 Day Hill Rd., Windsor, CT 06095 Call ~34.17 miles south of Chesterfield
  • We have a pool
  • 3 star Downtown property
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From$219
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Baymont by Wyndham East Windsor Bradley Airport 260 Main St., East Windsor, CT 06088 Call ~34.74 miles south of Chesterfield
  • Pool details: Indoor Pool/ open from 5:30AM-11:00PM
  • 3 star Suburban property
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From$40
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Ramada by Wyndham Windsor Locks 383 South Center St., Windsor Locks, CT 06096 Call ~35.20 miles south of Chesterfield
  • Pool details: 9am - 9pm. Indoor heated pool.
  • Mid-scale Airport hotel
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From$80
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Holiday Inn Express & Suites Brattleboro : 100 Chickering Dr. 100 Chickering Dr., Brattleboro, VT 05301 Call ~36.41 miles northeast of Chesterfield
  • Includes a pool: Indoor pool/ open 5am-11pm
  • 3-star Suburban property
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From$79
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Colonial Motel And Spa 889 Putney Rd., Brattleboro, VT 05301 Call ~36.48 miles northeast of Chesterfield
  • Pool available: INDOOR POOL: Monday-saturday 6am to 9pm Sunday : 8am to 9pm Holiday hours may vary It is 75feet Salt water pool with sauna,hot tub, limited gym equipment and locker room. OUTDOOR POOL: Seasonal. Open till dark.Not heated
  • Midscale Rural property
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From$59
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Marriott Hartford/Windsor Airport : 28 Day Hill Rd. 28 Day Hill Rd., Windsor, CT 06095 Call ~36.82 miles south of Chesterfield
  • Includes a pool: Inside pool open 7am - 11pm 24 Hour Fitness Center
  • Three Star Suburban property
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From$90
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Hyatt House Hartford North / Windsor 200 Corporate Dr., Windsor, CT 06095 Call ~37.07 miles south of Chesterfield
  • Pool available: Indoor heated pool and whirlpool 6 am - 9 pm *Limit four (4) guests per room
  • Midscale Suburban property
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From$89
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Comfort Inn & Suites Brattleboro I 91 1186 Putney Rd., Brattleboro, VT 05301 Call ~37.09 miles northeast of Chesterfield
  • Has swimming pool: open 6am-10pm indoor heated pool. 3 foot deep to 5 foot deep
  • Two-star Highway property
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From$79
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Hampton Inn Brattleboro - Brattleboro 1378 Putney Rd., Brattleboro, VT 05301 Call ~37.46 miles northeast of Chesterfield
  • Pool in hotel: Indoor heated salt water pool and whirl pool Tub. The pool is 4' - 5'deep 15'x30'
  • Three Star Rural property
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From$105
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Residence Inn by Marriott Hartford Windsor - Windsor 100 Dunfey Lane, Windsor, CT 06095 Call ~38.03 miles south of Chesterfield
  • Includes a pool: Outdoor pool only open Memorial Day - Labor Day 9a-9p daily.
  • 3 star Highway hotel
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From$96
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Hideaway Inn Mt. Snow 270 Handle Rd., Dover, VT 05356 Call ~39.39 miles north of Chesterfield
  • Has swimming pool: Heated Outdoor Pool: Open seasonally from late-May to mid-October, from 9:00 a.m. to 9:00 p.m.
  • Inexpensive Mountain hotel
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From$50
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Best Western Bennington in Bennington 220 Northside Dr., Bennington, VT 05201 Call ~39.82 miles northwest of Chesterfield
  • Has swimming pool: Outdoor, seasonal
  • 2-star Suburban property
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From$36
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Residence Inn by Marriott Hartford Avon 55 Simsbury Rd., Avon, CT 06001 Call ~39.88 miles south of Chesterfield
  • Pool details: Seasonal outdoor swimming pool and hot tub. Hours 9:00 AM - 9:00 PM.
  • Affordable Suburban property
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From$80
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Hampton Inn Bennington : 51 Hannaford Sq. 51 Hannaford Sq., Bennington, VT 05201 Call ~40.57 miles northwest of Chesterfield
  • Includes a pool: Indoor Pool is open from 7AM-10PM daily. Pool is 12,000 gallons
  • 3 star Mountain property
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From$80
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Newly Remodeled Residence Inn by Marriott Hartford Manchester - Manchester 201 Hale Rd., Manchester, CT 06042 Call ~43.07 miles southeast of Chesterfield
  • Pool available: Seasonal heated outdoor pool and hot tub
  • Midscale Suburban property
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From$109
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Homewood Suites by Hilton Hartford Manchester 109 Pavilions Dr., Manchester, CT 06042 Call ~43.17 miles south of Chesterfield
  • Includes a pool: Indoor Heated Pool and Whirlpool Tub
  • Mid-scale Suburban property
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From$99
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Hampton Inn Sturbridge 328 Main St., Sturbridge, MA 01566 Call ~43.25 miles east of Chesterfield
  • Pool in hotel
  • Midscale Highway property
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From$119
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