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
  • Has swimming pool: Indoor Heated Pool open from 7am - 9pm daily. Located on the first floor just off the lobby.
  • Midscale Suburban property
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From$109
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Towneplace Suites by Marriott 237 Russell St., Hadley, MA 01035 Call ~14.02 miles east of Chesterfield
  • Has swimming pool: Heated Indoor Pool open from 7am - 9pm daily.
  • Midscale Suburban hotel
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From$140
Average 3.0 /5 Review Score Call BookMore Details
Fairfield Inn & Suites Springfield Holyoke in Holyoke 229 Whiting Farms Rd., Holyoke, MA 01040 Call ~18.05 miles southeast of Chesterfield
  • Pool details: Indoor and heated pool open from 6AM to 10PM
  • 3 star Suburban property
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From$109
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Hampton Inn Chicopee / Springfield 600 Memorial Dr., Chicopee, MA 01020 Call ~20.13 miles southeast of Chesterfield
  • Pool details: Relax in our Indoor Pool open 9 AM - 10 PM.
  • Mid-scale Suburban property
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From$109
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Residence Inn by Marriott Springfield Chicopee 500 Memorial Dr., Chicopee, MA 01020 Call ~20.25 miles southeast of Chesterfield
  • Pool details: Indoor pool Pool Hours 6am to 11pm
  • 3-star Highway hotel
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From$99
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TRU by Hilton Chicopee Springfield 440 Memorial Dr., Chicopee, MA 01020 Call ~20.29 miles southeast of Chesterfield
  • Pool in hotel: Indoor Pool. Open 7AM-10PM daily.
  • Mid-scale property
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From$90
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Residence Inn by Marriott West Springfield - West Springfield 64 Border Way, West Springfield, MA 01089 Call ~20.55 miles southeast of Chesterfield
  • Pool details: Indoor pool open from 6am-12am daily
  • 3-star Highway property
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From$97
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Comfort Inn & Suites - West Springfield 106 Capital Dr., West Springfield, MA 01089 Call ~20.81 miles southeast of Chesterfield
  • Pool in hotel: Indoor pool and whirlpool open daily from 7am-10pm
  • Low Cost 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
  • Has swimming pool: Covered seasonal outdoor pool Handicapped lift open 10am to 10pm
  • Economy 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
  • We have a pool ready for use
  • Affordable hotel
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From$90
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Holiday Inn Express Pittsfield Lenox Berkshires - Pittsfield 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
  • 3-star Suburban hotel
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From$80
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Berkshire Mountain Lodge : 8 Dan Fox Dr. 8 Dan Fox Dr., Pittsfield, MA 01201 Call ~21.64 miles west of Chesterfield
  • Pool available: Indoor pool & hot tub Open daily 8am-11pm
  • Cheap Mountain property
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From$125
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Hilton Garden Inn Lenox Pittsfield - Pittsfield 1032 South St., Pittsfield, MA 01201 Call ~21.71 miles west of Chesterfield
  • Includes a pool: Indoor heated pool/hot tub
  • Midscale Suburban hotel
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From$95
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Best Western Springfield West Inn : 429 Riverdale St. 429 Riverdale St., West Springfield, MA 01089 Call ~21.92 miles southeast of Chesterfield
  • With a pool!
  • Affordable hotel
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From$73
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The Black Swan Lee Lenox An Ascend Collection Hotel 435 Laurel St., Lee, MA 01238 Call ~21.92 miles west of Chesterfield
  • With a pool!
  • 3 star Lake hotel
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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.
  • Affordable Downtown hotel
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From$80
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Holiday Inn Club Vacations Oak N Spruce Resort in South Lee 190 Meadow St., South Lee, MA 01260 Call ~23.58 miles west of Chesterfield
  • Pool details: Two outdoor pools (seasonal) Two indoor pools (hours vary) Hot Tub (hours vary)
  • Midscale Mountain hotel
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From$89
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Sheraton Springfield - Springfield 1 Monarch Place, Springfield, MA 01144 Call ~23.71 miles southeast of Chesterfield
  • Pool available: We have an indoor pool with an outdoor patio area. Weekday Hours: 5:30am-10pm Saturday Hours: 8am-10pm Sunday Hours: 8am-8pm
  • Affordable 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 details: Indoor heated pool
  • 3-star hotel
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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
  • Includes a pool: Heated indoor pool open 7am - 9pm daily.
  • 3-star 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
  • Includes a pool: 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.
  • Affordable Mountain hotel
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From$75
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Hotel Downstreet Ascend Hotel Collection in North Adams 40 Main St., North Adams, MA 01247 Call ~25.37 miles northwest of Chesterfield
  • Includes a pool: 5am-10pm Indoor
  • 3-star Downtown hotel
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From$136
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The Porches Inn at Mass Moca 231 River St., North Adams, MA 01247 Call ~25.56 miles northwest of Chesterfield
  • Pool details: Outdoor heated pool open 24 hours daily year round. Sauna, outdoor hot tub and 24 hour fitness Center onsite.
  • Expensive Downtown property
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From$199
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Jiminy Peak Mountain Resort 37 Corey Rd., Hancock, MA 01237 Call ~25.75 miles west of Chesterfield
  • Pool available: Country Inn Pool is open 8a - 10p daily. Outdoor heated pool open year round.
  • Three Star Mountain hotel
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From$105
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Maple Terrace Motel : 555 Main St. 555 Main St., Williamstown, MA 01267 Call ~28.26 miles northwest of Chesterfield
  • Pool in hotel: Beautiful secluded heated pool with amazing and breathtaking views. Opens Daily 9 AM and closes at Dusk.
  • Inexpensive Rural hotel
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From$59
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Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi 249 Stockbridge Rd., Great Barrington, MA 01230 Call ~28.81 miles west of Chesterfield
  • Pool in hotel
  • Mid-scale Resort property
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From$109
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Hilton Garden Inn - Babc2af01bf25d1094cea9b5604bcbb1 Hartford North / Bradley Intl Airport, Babc2af01bf25d1094cea9b5604bcbb1, CT 06095 Call ~32.24 miles south of Chesterfield
  • Has swimming pool: 5:00am- 10:00pm
  • Affordable Airport hotel
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From$80
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The White House Inn 178 Vt 9 East, Wilmington, VT 05363 Call ~32.59 miles north of Chesterfield
  • Pool details: Small, shallow indoor pool, open 24 hours a day
  • Four star Mountain property
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From$75
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Holiday Inn Express & Suites Bradley Airport by IHG 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.
  • Midscale Airport property
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From$85
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Springhill Suites Marriott Airport 225 Ella Grasso Turnpike, Windsor Locks, CT 06096 Call ~32.98 miles south of Chesterfield
  • Pool in hotel: Small indoor heated pool. Not big enough for large groups of people.
  • Mid-scale Airport hotel
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From$95
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Econo Lodge Inn & Suites Windsor Locks Bradley Airport in Windsor Locks 34 Old County Rd., Windsor Locks, CT 06096 Call ~33.28 miles south of Chesterfield
  • Pool details: Seasonal-Outdoor
  • Economical Airport hotel
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From$45
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Econo Lodge Brattleboro South : 515 Canal St. 515 Canal St., Brattleboro, VT 05301 Call ~33.78 miles northeast of Chesterfield
  • We have a pool ready for use
  • 2 star Downtown property
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From$53
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Courtyard By Marriott Hartford/Windsor Airport - Windsor 1 Day Hill Rd., Windsor, CT 06095 Call ~34.17 miles south of Chesterfield
  • We have a pool
  • Three Star Downtown property
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From$219
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Baymont by Wyndham East Windsor Bradley Airport : 260 Main St. 260 Main St., East Windsor, CT 06088 Call ~34.74 miles south of Chesterfield
  • Has swimming pool: Indoor Pool/ open from 5:30AM-11:00PM
  • Affordable Suburban hotel
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From$40
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Ramada by Wyndham Windsor Locks : 383 South Center St. 383 South Center St., Windsor Locks, CT 06096 Call ~35.20 miles south of Chesterfield
  • Has swimming pool: 9am - 9pm. Indoor heated pool.
  • Midscale Airport property
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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
  • Three Star Suburban hotel
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From$79
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Colonial Motel And Spa in Brattleboro 889 Putney Rd., Brattleboro, VT 05301 Call ~36.48 miles northeast of Chesterfield
  • Includes a pool: 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
  • Mid-scale Rural hotel
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From$59
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Marriott Hartford/Windsor Airport in Windsor 28 Day Hill Rd., Windsor, CT 06095 Call ~36.82 miles south of Chesterfield
  • Pool available: Inside pool open 7am - 11pm 24 Hour Fitness Center
  • 3 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
  • Affordable Suburban property
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From$89
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Comfort Inn & Suites Brattleboro I 91 - Brattleboro 1186 Putney Rd., Brattleboro, VT 05301 Call ~37.09 miles northeast of Chesterfield
  • Includes a pool: open 6am-10pm indoor heated pool. 3 foot deep to 5 foot deep
  • Two star Highway hotel
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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 details: Indoor heated salt water pool and whirl pool Tub. The pool is 4' - 5'deep 15'x30'
  • 3-star Rural hotel
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From$105
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Residence Inn by Marriott Hartford Windsor : 100 Dunfey Lane 100 Dunfey Lane, Windsor, CT 06095 Call ~38.03 miles south of Chesterfield
  • Pool available: Outdoor pool only open Memorial Day - Labor Day 9a-9p daily.
  • Mid-scale 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
  • Pool available: Heated Outdoor Pool: Open seasonally from late-May to mid-October, from 9:00 a.m. to 9:00 p.m.
  • Low-priced Mountain property
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From$50
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Best Western Bennington 220 Northside Dr., Bennington, VT 05201 Call ~39.82 miles northwest of Chesterfield
  • Pool in hotel: Outdoor, seasonal
  • Economical Suburban hotel
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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
  • Includes a pool: Seasonal outdoor swimming pool and hot tub. Hours 9:00 AM - 9:00 PM.
  • 3-star Suburban property
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From$80
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Hampton Inn Bennington - Bennington 51 Hannaford Sq., Bennington, VT 05201 Call ~40.57 miles northwest of Chesterfield
  • Has swimming pool: Indoor Pool is open from 7AM-10PM daily. Pool is 12,000 gallons
  • Three Star Mountain property
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From$80
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Newly Remodeled Residence Inn by Marriott Hartford Manchester in Manchester 201 Hale Rd., Manchester, CT 06042 Call ~43.07 miles southeast of Chesterfield
  • Has swimming pool: 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. 109 Pavilions Dr., Manchester, CT 06042 Call ~43.17 miles south of Chesterfield
  • Includes a pool: Indoor Heated Pool and Whirlpool Tub
  • Affordable 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
  • Our hotel comes with a pool
  • Three Star Highway hotel
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From$119
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Publick House Historic Inn and Country Motor Lodge : 277 Main St. (Rt 131) 277 Main St. (Rt 131), Sturbridge, MA 01566 Call ~43.53 miles east of Chesterfield
  • Pool in hotel: Outdoor Pool
  • Inexpensive Rural hotel
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From$61
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