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

Fairfield Inn & Suites Springfield Northampton / Amherst 115a Conz St., Northampton, MA 01060 Call ~12.19 miles east of Chesterfield
  • With a pool!
  • Three Star property
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From$118 total
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Quality Inn & Suites Northampton Amherst 117 Conz St., Northampton, MA 01060 Call ~12.26 miles east of Chesterfield
  • Has swimming pool: open from 6am - 10pm Heated indoor pool 5 1/3 in depth
  • 2-star Highway property
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From$102 total
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Hampton Inn Hadley Amherst Area - Hadley 24 Bay Rd., Hadley, MA 01035 Call ~12.62 miles east of Chesterfield
  • Pool in hotel: Indoor Heated Pool open from 7am - 9pm daily. Located on the first floor just off the lobby.
  • Three Star Suburban hotel
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From$130 total
Very Good 4.0 /5 Reviews Call BookMore Details
Towneplace Suites by Marriott 237 Russell St., Hadley, MA 01035 Call ~14.02 miles east of Chesterfield
  • Pool in hotel: Heated Indoor Pool open from 7am - 9pm daily.
  • 3-star Suburban property
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From$168 total
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Comfort Inn & Suites Hadley - Amherst : 400 Russell St. 400 Russell St., Hadley, MA 01035 Call ~15.18 miles east of Chesterfield
  • With a pool!
  • 3 star Downtown hotel
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From$106 total
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Courtyard by Marriott Hadley Amherst - Hadley 423 Russell St., Hadley, MA 01035 Call ~15.43 miles east of Chesterfield
  • Pool available: 6AM-11PM Indoor Pool & Spa
  • Midscale Downtown property
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From$130 total
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Fairfield Inn & Suites Springfield Holyoke 229 Whiting Farms Rd., Holyoke, MA 01040 Call ~18.05 miles southeast of Chesterfield
  • Pool available: Indoor and heated pool open from 6AM to 10PM
  • Three Star Suburban property
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From$130 total
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Hampton Inn Chicopee / Springfield 600 Memorial Dr., Chicopee, MA 01020 Call ~20.13 miles southeast of Chesterfield
  • Pool in hotel: Relax in our Indoor Pool open 9 AM - 10 PM.
  • 3 star Suburban hotel
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From$130 total
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Residence Inn by Marriott Springfield Chicopee 500 Memorial Dr., Chicopee, MA 01020 Call ~20.25 miles southeast of Chesterfield
  • Has swimming pool: Indoor pool Pool Hours 9am to 10pm
  • Midscale Highway property
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From$118 total
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TRU by Hilton Chicopee Springfield : 440 Memorial Dr. 440 Memorial Dr., Chicopee, MA 01020 Call ~20.28 miles southeast of Chesterfield
  • Includes a pool: Indoor Pool. Open 7AM-10PM daily.
  • Mid-scale hotel
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From$118 total
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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
  • 3 star Highway property
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From$116 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Comfort Inn & Suites : 106 Capital Dr. 106 Capital Dr., West Springfield, MA 01089 Call ~20.81 miles southeast of Chesterfield
  • Pool available: Indoor pool and whirlpool open daily from 7am-10pm
  • Low-priced Suburban property
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From$154 total
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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
  • Cheap Suburban property
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From$90 total
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Courtyard West Spring Marriott 885 Riverdale St., West Springfield, MA 01089 Call ~21.27 miles southeast of Chesterfield
  • Has a pool!
  • Mid-scale hotel
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From$108 total
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Holiday Inn Express Pittsfield Lenox Berkshires 1055 South St., Pittsfield, MA 01201 Call ~21.56 miles west of Chesterfield
  • Pool in hotel: Indoor heated pool & hot tub, hours: 8am - 10pm, Deep end: 5 feet
  • 3-star Suburban property
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From$96 total
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Berkshire Mountain Lodge in Pittsfield 8 Dan Fox Dr., Pittsfield, MA 01201 Call ~21.64 miles west of Chesterfield
  • Pool in hotel: Indoor pool & hot tub Open daily 8am-11pm
  • Two star Mountain hotel
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From$150 total
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Hilton Garden Inn Lenox Pittsfield 1032 South St., Pittsfield, MA 01201 Call ~21.71 miles west of Chesterfield
  • Pool in hotel: Indoor heated pool/hot tub
  • 3 star Suburban property
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From$114 total
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Hampton Inn & Suites Lenox Berkshires in Lenox 445 Pittsfield Rd., Lenox, MA 01240 Call ~21.84 miles west of Chesterfield
  • Our hotel comes with a pool
  • 3-star Mountain hotel
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From$96 total
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Best Western Springfield West Inn - West Springfield 429 Riverdale St., West Springfield, MA 01089 Call ~21.92 miles southeast of Chesterfield
  • Our hotel comes with a pool
  • Mid-scale hotel
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From$87 total
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La Quinta by Wyndham in Springfield 100 Congress St., Springfield, MA 01104 Call ~23.19 miles southeast of Chesterfield
  • Includes a pool: Heated indoor pool open daily 7am - 9pm. Located just off the lobby on the first floor next to the small arcade.
  • Midscale Downtown property
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From$96 total
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Holiday Inn Club Vacations Oak N Spruce Resort 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 hotel
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From$106 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Sheraton Springfield Monarch Place Hotel 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
  • 3-star Downtown hotel
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From$96 total
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Holiday Inn Express Springfield Downtown - Springfield 145 State St., Springfield, MA 01103 Call ~23.87 miles southeast of Chesterfield
  • Pool details: Indoor heated pool
  • Mid-scale hotel
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From$96 total
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Hampton Inn & Suites Springfield/Downtown 851 East Columbus Ave., Springfield, MA 01105 Call ~24.46 miles southeast of Chesterfield
  • Pool in hotel: 7am-10Pm
  • Affordable Downtown hotel
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From$118 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Vacation Village in The Berkshires : 276 Brodie Mtn Rd. 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.
  • 3 star Mountain hotel
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From$90 total
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The Red Lion Inn - Stockbridge 30 Main St., Stockbridge, MA 01262 Call ~25.25 miles west of Chesterfield
  • Pool available: Year-round pool & hot tub. Our fabulous heated lap pool and hot-tub are open all year, and located right in the center of our property. In the summer months, enjoy the historic pool house with a cocktail and a rousing game of ping pong!
  • Mid-scale Rural hotel
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From$144 total
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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$238 total
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Jiminy Peak Mountain Resort in Hancock 37 Corey Rd., Hancock, MA 01237 Call ~25.75 miles west of Chesterfield
  • Includes a pool: Country Inn Pool is open 8a - 10p daily. Outdoor heated pool open year round.
  • Mid-scale Mountain property
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From$126 total
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The Orchards Hotel 222 Adams Rd., Williamstown, MA 01267 Call ~28.06 miles northwest of Chesterfield
  • Our hotel comes with a pool
  • High-end Suburban property
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From$130 total
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Maple Terrace Motel : 555 Main St. 555 Main St., Williamstown, MA 01267 Call ~28.26 miles northwest of Chesterfield
  • Pool available: Beautiful secluded heated pool with amazing and breathtaking views. Opens Daily 9 AM and closes at Dusk.
  • Economical Rural property
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From$70 total
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Fairfield Inn & Suites by Marriott Springfield Enfield 1 Bright Meadow Blvd., Enfield, CT 06082 Call ~28.78 miles southeast of Chesterfield
  • Pool in hotel: Seasonal Outdoor Pool- 9am-9pm
  • Three Star Suburban hotel
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From$94 total
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Fairfield Inn & Suites by Marriott Great Barrington Lenox / Berks - Great Barrington 249 Stockbridge Rd., Great Barrington, MA 01230 Call ~28.81 miles west of Chesterfield
  • Includes a pool
  • Three Star Resort property
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From$130 total
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The Williams Inn 1090 Main St., Williamstown, MA 01267 Call ~29.07 miles northwest of Chesterfield
  • Has swimming pool: Indoor heated pool and hot tub.
  • High end Suburban property
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From$114 total
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Hilton Garden Inn Hartford North / Bradley Intl Airport, Babc2af01bf25d1094cea9b5604bcbb1, CT 06095 Call ~32.24 miles south of Chesterfield
  • Pool details: 5:00am- 10:00pm
  • Mid-scale Airport property
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From$96 total
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The White House Inn 178 Vt 9 East, Wilmington, VT 05363 Call ~32.59 miles north of Chesterfield
  • Pool available: Small, shallow indoor pool, open 24 hours a day
  • 4 star Mountain hotel
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From$90 total
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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 in hotel: Small indoor heated pool. Not big enough for large groups of people.
  • 3 star Airport property
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From$114 total
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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 available: Seasonal-Outdoor
  • Low Cost Airport hotel
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From$54 total
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Fairfield Inn & Suites by Marriott Hartford Airport 2 Loten Dr., Windsor Locks, CT 06096 Call ~33.71 miles south of Chesterfield
  • Pool available: Indoor Pool Open Monday - Sunday from 8am until 10pm 35 ft 10" by 17 ft 8"
  • Midscale Airport property
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From$114 total
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Homewood Suites by Hilton Windsor Locks Hartford - Windsor Locks 65 Ella Grasso Turnpike, Windsor Locks, CT 06096 Call ~33.76 miles south of Chesterfield
  • Pool available: We offer an outside swimming pool that is open from Memorial Day weekend through Labor Day weekend. Hours of operation daily: 10am-9pm.
  • Mid-scale Airport hotel
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From$118 total
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Econo Lodge Brattleboro South in Brattleboro 515 Canal St., Brattleboro, VT 05301 Call ~33.78 miles northeast of Chesterfield
  • Has a pool!
  • 2-star Downtown property
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From$63 total
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Doubletree by Hilton Hotel Hartford Bradley Airport in Windsor Locks 16 Ella T Grasso Turnpike, Windsor Locks, CT 06096 Call ~33.79 miles south of Chesterfield
  • Includes a pool: The hotel offers an indoor heated pool. It is open from 7am-10pm daily
  • 3-star Airport hotel
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From$87 total
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Courtyard By Marriott Hartford/Windsor Airport : 1 Day Hill Rd. 1 Day Hill Rd., Windsor, CT 06095 Call ~34.17 miles south of Chesterfield
  • Pool in hotel
  • Affordable Downtown property
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From$262 total
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Baymont by Wyndham East Windsor Bradley Airport in East Windsor 260 Main St., East Windsor, CT 06088 Call ~34.74 miles south of Chesterfield
  • Pool in hotel: Indoor Pool/ open from 5:30AM-11:00PM
  • 3-star Suburban property
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From$48 total
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Ramada by Wyndham Windsor Locks - Windsor Locks 383 South Center St., Windsor Locks, CT 06096 Call ~35.20 miles south of Chesterfield
  • Pool available: 9am - 9pm. Indoor heated pool.
  • Affordable Airport hotel
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From$96 total
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Holiday Inn Express & Suites Brattleboro - Brattleboro 100 Chickering Dr., Brattleboro, VT 05301 Call ~36.41 miles northeast of Chesterfield
  • Pool in hotel: Indoor pool/ open 5am-11pm
  • Midscale Suburban hotel
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From$94 total
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Black Mountain Inn : 959 Putney Rd. 959 Putney Rd., Brattleboro, VT 05301 Call ~36.60 miles northeast of Chesterfield
  • Includes a pool: Seasonal outdoor pool
  • Low Cost Suburban hotel
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From$68 total
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Hyatt House Hartford North / Windsor : 200 Corporate Dr. 200 Corporate Dr., Windsor, CT 06095 Call ~37.07 miles south of Chesterfield
  • Has swimming pool: Indoor heated pool and whirlpool 6 am - 9 pm *Limit four (4) guests per room
  • Three Star Suburban property
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From$106 total
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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
  • Economy Highway hotel
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From$94 total
Very Good 4.0 /5 Review Score Call BookMore Details
Hampton Inn Brattleboro in Brattleboro 1378 Putney Rd., Brattleboro, VT 05301 Call ~37.46 miles northeast of Chesterfield
  • Pool available: 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$126 total
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Residence Inn by Marriott Hartford Windsor 100 Dunfey Lane, Windsor, CT 06095 Call ~38.03 miles south of Chesterfield
  • Pool details: Outdoor pool only open Memorial Day - Labor Day 9a-9p daily.
  • Three Star Highway property
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From$115 total
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