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.

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Chesterfield Hotels with Outdoor or Indoor Pools

Hampton Inn Hadley Amherst Area - Hadley 24 Bay Rd., Hadley, MA 01035
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~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.
  • Midscale Suburban hotel
More Photos Photo of Hampton Inn Hadley Amherst Area Pool
From$109
Very Good 4.0 /5 Reviews Call BookMore Details
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Towneplace Suites by Marriott - Hadley 237 Russell St., Hadley, MA 01035
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~14.02 miles east of Chesterfield
  • Pool in hotel: Heated Indoor Pool open from 7am - 9pm daily.
  • Three Star Suburban hotel
More Photos Swimming pool at Towneplace Suites by Marriott
From$140
Average 3.0 /5 Hotel Reviews Call BookMore Details
Courtyard by Marriott Hadley Amherst 423 Russell St., Hadley, MA 01035
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~15.43 miles east of Chesterfield
  • Pool in hotel: 6AM-11PM Indoor Pool & Spa
  • Three Star Downtown hotel
More Photos Swimming pool at Courtyard by Marriott Hadley Amherst
From$109
Very Good 4.0 /5 Reviews Call BookMore Details
Fairfield Inn & Suites Springfield Holyoke 229 Whiting Farms Rd., Holyoke, MA 01040
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~18.05 miles southeast of Chesterfield
  • Pool available: Indoor and heated pool open from 6AM to 10PM
  • Mid-scale Suburban property
More Photos Pool image of Fairfield Inn & Suites Springfield Holyoke
From$109
Very Good 4.0 /5 Reviews Call BookMore Details
Hampton Inn Chicopee / Springfield 600 Memorial Dr., Chicopee, MA 01020
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~20.13 miles southeast of Chesterfield
  • Has swimming pool: Relax in our Indoor Pool open 9 AM - 10 PM.
  • Mid-scale Suburban hotel
More Photos Pool image of Hampton Inn Chicopee / Springfield
From$109
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Residence Inn by Marriott Springfield Chicopee 500 Memorial Dr., Chicopee, MA 01020
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~20.25 miles southeast of Chesterfield
  • Pool available: Indoor pool Pool Hours 9am to 10pm
  • 3 star Highway property
More Photos Pool image of Residence Inn by Marriott Springfield Chicopee
From$99
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TRU by Hilton Chicopee Springfield 440 Memorial Dr., Chicopee, MA 01020
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~20.29 miles southeast of Chesterfield
  • Pool available: Indoor Pool. Open 7AM-10PM daily.
  • Affordable property
More Photos Swimming pool at TRU by Hilton Chicopee Springfield
From$90
Very Good 4.0 /5 Review Score Call BookMore Details
Residence Inn by Marriott West Springfield 64 Border Way, West Springfield, MA 01089
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~20.55 miles southeast of Chesterfield
  • Has swimming pool: Indoor pool open from 6am-12am daily
  • Midscale Highway hotel
More Photos Pool image of Residence Inn by Marriott West Springfield
From$97
Very Good 4.0 /5 Reviews Call BookMore Details
Comfort Inn & Suites : 106 Capital Dr. 106 Capital Dr., West Springfield, MA 01089
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~20.81 miles southeast of Chesterfield
  • Includes a pool: Indoor pool and whirlpool open daily from 7am-10pm
  • Economical Suburban property
More Photos Swimming pool at Comfort Inn & Suites
From$129
Average 3.0 /5 Latest Reviews Call BookMore Details
Quality Inn West Springfield 1150 Riverdale St., West Springfield, MA 01089
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~20.86 miles southeast of Chesterfield
  • Includes a pool: Covered seasonal outdoor pool Handicapped lift open 10am to 10pm
  • Two star Suburban property
More Photos Pool image of Quality Inn West Springfield
From$75
Average 3.0 /5 Reviews Call BookMore Details
Courtyard West Spring Marriott - West Springfield 885 Riverdale St., West Springfield, MA 01089
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~21.27 miles southeast of Chesterfield
  • We have a pool ready for use
  • Midscale hotel
More Photos Photo of Courtyard West Spring Marriott Pool
From$90
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Pittsfield Lenox Berkshires 1055 South St., Pittsfield, MA 01201
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~21.56 miles west of Chesterfield
  • Has swimming pool: Indoor heated pool & hot tub, hours: 8am - 10pm, Deep end: 5 feet
  • Midscale Suburban hotel
More Photos Photo of Holiday Inn Express Pittsfield Lenox Berkshires Pool
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Berkshire Mountain Lodge 8 Dan Fox Dr., Pittsfield, MA 01201
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~21.64 miles west of Chesterfield
  • Pool details: Indoor pool & hot tub Open daily 8am-11pm
  • Low Cost Mountain property
More Photos Swimming pool at Berkshire Mountain Lodge
From$125
Very Good 4.5 /5 Latest Reviews Call BookMore Details
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Hilton Garden Inn Lenox Pittsfield in Pittsfield 1032 South St., Pittsfield, MA 01201
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~21.71 miles west of Chesterfield
  • Includes a pool: Indoor heated pool/hot tub
  • Mid-scale Suburban hotel
More Photos Photo of Hilton Garden Inn Lenox Pittsfield Pool
From$95
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Lenox Berkshires 445 Pittsfield Rd., Lenox, MA 01240
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~21.84 miles west of Chesterfield
  • Pool in hotel
  • Midscale Mountain hotel
More Photos Swimming pool at Hampton Inn & Suites Lenox Berkshires
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
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Best Western Springfield West Inn in West Springfield 429 Riverdale St., West Springfield, MA 01089
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~21.92 miles southeast of Chesterfield
  • Has swimming pool
  • Affordable hotel
More Photos Photo of Best Western Springfield West Inn Pool
From$73
Average 3.0 /5 Reviews Call BookMore Details
La Quinta by Wyndham 100 Congress St., Springfield, MA 01104
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~23.19 miles southeast of Chesterfield
  • Has swimming pool: Heated indoor pool open daily 7am - 9pm. Located just off the lobby on the first floor next to the small arcade.
  • Three Star Downtown hotel
More Photos Pool image of La Quinta by Wyndham
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort - South Lee 190 Meadow St., South Lee, MA 01260
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~23.58 miles west of Chesterfield
  • Pool available: Two outdoor pools (seasonal) Two indoor pools (hours vary) Hot Tub (hours vary)
  • Affordable Mountain property
More Photos Pool image of Holiday Inn Club Vacations Oak N Spruce Resort
From$89
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Sheraton Springfield Monarch Place Hotel : 1 Monarch Place 1 Monarch Place, Springfield, MA 01144
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~23.72 miles southeast of Chesterfield
  • Has swimming pool: We have an indoor pool with an outdoor patio area. Weekday Hours: 5:30am-10pm Saturday Hours: 8am-10pm Sunday Hours: 8am-8pm
  • Mid-scale Downtown property
More Photos Pool image of Sheraton Springfield Monarch Place Hotel
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Springfield Downtown 145 State St., Springfield, MA 01103
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~23.87 miles southeast of Chesterfield
  • Includes a pool: Indoor heated pool
  • Mid-scale hotel
More Photos hotel room
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express Ludlow by IHG in Ludlow 321 Center St., Ludlow, MA 01056
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~24.05 miles southeast of Chesterfield
  • Pool available: Heated indoor pool open 7am - 9pm daily.
  • 3 star Highway hotel
More Photos Swimming pool at Holiday Inn Express Ludlow by IHG
From$89
Very Good 4.0 /5 Review Score Call BookMore Details
Vacation Village in The Berkshires in Lanesborough 276 Brodie Mtn Rd., Lanesborough, MA 01237
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~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 property
More Photos Pool image of Vacation Village in The Berkshires
From$75
Very Good 4.0 /5 Reviews Call BookMore Details
The Red Lion Inn 30 Main St., Stockbridge, MA 01262
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~25.25 miles west of Chesterfield
  • Pool details: 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!
  • Affordable Rural property
More Photos Photo of The Red Lion Inn Pool
From$120
Average 3.0 /5 Reviews Call BookMore Details
The Porches Inn at Mass Moca - North Adams 231 River St., North Adams, MA 01247
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~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.
  • Four-star Downtown hotel
More Photos Swimming pool at The Porches Inn at Mass Moca
From$199
Very Good 4.0 /5 Review Score Call BookMore Details
Jiminy Peak Mountain Resort in Hancock 37 Corey Rd., Hancock, MA 01237
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~25.75 miles west of Chesterfield
  • Pool in hotel: Country Inn Pool is open 8a - 10p daily. Outdoor heated pool open year round.
  • 3 star Mountain property
More Photos Swimming pool at Jiminy Peak Mountain Resort
From$105
Very Good 4.0 /5 Read Reviews Call BookMore Details
Maple Terrace Motel - Williamstown 555 Main St., Williamstown, MA 01267
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~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.
  • Two-star Rural property
More Photos Swimming pool at Maple Terrace Motel
From$59
Very Good 4.0 /5 Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi in Great Barrington 249 Stockbridge Rd., Great Barrington, MA 01230
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~28.81 miles west of Chesterfield
  • Pool in hotel
  • Three Star Resort hotel
More Photos Pool image of Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi
From$109
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn in Babc2af01bf25d1094cea9b5604bcbb1 Hartford North / Bradley Intl Airport, Babc2af01bf25d1094cea9b5604bcbb1, CT 06095
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~32.24 miles south of Chesterfield
  • Pool available: 5:00am- 10:00pm
  • Midscale Airport hotel
More Photos Pool image of Hilton Garden Inn
From$80
Average 3.0 /5 Review Score Call BookMore Details
The White House Inn : 178 Vt 9 East 178 Vt 9 East, Wilmington, VT 05363
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~32.59 miles north of Chesterfield
  • Pool details: Small, shallow indoor pool, open 24 hours a day
  • 4-star Mountain property
More Photos Photo of The White House Inn Pool
From$75
Average 3.0 /5 Latest Reviews Call BookMore Details
Springhill Suites Marriott Airport : 225 Ella Grasso Turnpike 225 Ella Grasso Turnpike, Windsor Locks, CT 06096
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~32.98 miles south of Chesterfield
  • Includes a pool: Small indoor heated pool. Not big enough for large groups of people.
  • 3 star Airport hotel
More Photos Swimming pool at Springhill Suites Marriott Airport
From$95
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Econo Lodge Inn & Suites Windsor Locks Bradley Airport 34 Old County Rd., Windsor Locks, CT 06096
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~33.28 miles south of Chesterfield
  • Includes a pool: Seasonal-Outdoor
  • Low Cost Airport hotel
More Photos Swimming pool at Econo Lodge Inn & Suites Windsor Locks Bradley Airport
From$45
Average 3.0 /5 Hotel Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Hartford Airport in Windsor Locks 2 Loten Dr., Windsor Locks, CT 06096
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~33.71 miles south of Chesterfield
  • Includes a pool: Indoor Pool Open Monday - Sunday from 8am until 10pm 35 ft 10" by 17 ft 8"
  • Affordable Airport hotel
More Photos Photo of Fairfield Inn & Suites by Marriott Hartford Airport Pool
From$95
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Homewood Suites by Hilton Windsor Locks Hartford in Windsor Locks 65 Ella Grasso Turnpike, Windsor Locks, CT 06096
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~33.76 miles south of Chesterfield
  • Pool in hotel: We offer an outside swimming pool that is open from Memorial Day weekend through Labor Day weekend. Hours of operation daily: 9am-10pm.
  • Affordable Airport property
More Photos Pool image of Homewood Suites by Hilton Windsor Locks Hartford
From$99
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Econo Lodge Brattleboro South 515 Canal St., Brattleboro, VT 05301
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~33.78 miles northeast of Chesterfield
  • We have a pool
  • Low priced Downtown property
More Photos Photo of Econo Lodge Brattleboro South Pool
From$53
Not Good 1.0 /5 Recent Reviews Call BookMore Details
Courtyard By Marriott Hartford/Windsor Airport 1 Day Hill Rd., Windsor, CT 06095
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~34.17 miles south of Chesterfield
  • Includes a pool
  • Three Star Downtown property
More Photos Swimming pool at Courtyard By Marriott Hartford/Windsor Airport
From$219
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Baymont by Wyndham East Windsor Bradley Airport : 260 Main St. 260 Main St., East Windsor, CT 06088
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~34.74 miles south of Chesterfield
  • Pool in hotel: Indoor Pool/ open from 5:30AM-11:00PM
  • 3 star Suburban hotel
More Photos Pool image of Baymont by Wyndham East Windsor Bradley Airport
From$40
Average 3.0 /5 Reviews Call BookMore Details
Ramada by Wyndham Windsor Locks 383 South Center St., Windsor Locks, CT 06096
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~35.20 miles south of Chesterfield
  • Includes a pool: 9am - 9pm. Indoor heated pool.
  • Three Star Airport property
More Photos Swimming pool at Ramada by Wyndham Windsor Locks
From$80
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Express & Suites Brattleboro in Brattleboro 100 Chickering Dr., Brattleboro, VT 05301
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~36.41 miles northeast of Chesterfield
  • Has swimming pool: Indoor pool/ open 5am-11pm
  • Midscale Suburban property
More Photos Photo of Holiday Inn Express & Suites Brattleboro Pool
From$79
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Colonial Motel And Spa 889 Putney Rd., Brattleboro, VT 05301
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~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
  • Three Star Rural hotel
More Photos Pool image of Colonial Motel And Spa
From$59
Average 3.0 /5 Recent Reviews Call BookMore Details
Marriott Hartford/Windsor Airport 28 Day Hill Rd., Windsor, CT 06095
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~36.82 miles south of Chesterfield
  • Includes a pool: Inside pool open 7am - 11pm 24 Hour Fitness Center
  • 3 star Suburban hotel
More Photos Photo of Marriott Hartford/Windsor Airport Pool
From$90
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hyatt House Hartford North / Windsor 200 Corporate Dr., Windsor, CT 06095
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~37.07 miles south of Chesterfield
  • Pool details: Indoor heated pool and whirlpool 6 am - 9 pm *Limit four (4) guests per room
  • Mid-scale Suburban property
More Photos Photo of Hyatt House Hartford North / Windsor Pool
From$89
Average 3.0 /5 Recent Reviews Call BookMore Details
Comfort Inn & Suites Brattleboro I 91 in Brattleboro 1186 Putney Rd., Brattleboro, VT 05301
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~37.09 miles northeast of Chesterfield
  • Pool available: open 6am-10pm indoor heated pool. 3 foot deep to 5 foot deep
  • Cheap Highway hotel
More Photos Swimming pool at Comfort Inn & Suites Brattleboro I 91
From$79
Very Good 4.0 /5 Review Score Call BookMore Details
Hampton Inn Brattleboro : 1378 Putney Rd. 1378 Putney Rd., Brattleboro, VT 05301
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~37.46 miles northeast of Chesterfield
  • Includes a pool: Indoor heated salt water pool and whirl pool Tub. The pool is 4' - 5'deep 15'x30'
  • Midscale Rural hotel
More Photos Swimming pool at Hampton Inn Brattleboro
From$105
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Residence Inn by Marriott Hartford Windsor : 100 Dunfey Lane 100 Dunfey Lane, Windsor, CT 06095
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~38.03 miles south of Chesterfield
  • Pool available: Outdoor pool only open Memorial Day - Labor Day 9a-9p daily.
  • Midscale Highway hotel
More Photos Photo of Residence Inn by Marriott Hartford Windsor Pool
From$96
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Hideaway Inn Mt. Snow 270 Handle Rd., Dover, VT 05356
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~39.39 miles north of Chesterfield
  • Pool details: Heated Outdoor Pool: Open seasonally from late-May to mid-October, from 9:00 a.m. to 9:00 p.m.
  • Low Cost Mountain hotel
More Photos Pool image of Hideaway Inn Mt. Snow
From$50
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Best Western Bennington 220 Northside Dr., Bennington, VT 05201
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~39.82 miles northwest of Chesterfield
  • Has swimming pool: Outdoor, seasonal
  • Two-star Suburban hotel
More Photos Swimming pool at Best Western Bennington
From$36
Very Good 4.0 /5 Reviews Call BookMore Details
Residence Inn by Marriott Hartford Avon : 55 Simsbury Rd. 55 Simsbury Rd., Avon, CT 06001
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~39.88 miles south of Chesterfield
  • Has swimming pool: Seasonal outdoor swimming pool and hot tub. Hours 9:00 AM - 9:00 PM.
  • Three Star Suburban hotel
More Photos Swimming pool at Residence Inn by Marriott Hartford Avon
From$80
Very Good 4.0 /5 Review Score Call BookMore Details
Hampton Inn Bennington : 51 Hannaford Sq. 51 Hannaford Sq., Bennington, VT 05201
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~40.57 miles northwest of Chesterfield
  • Pool available: Indoor Pool is open from 7AM-10PM daily. Pool is 12,000 gallons
  • Three Star Mountain hotel
More Photos Photo of Hampton Inn Bennington Pool
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Newly Remodeled Residence Inn by Marriott Hartford Manchester : 201 Hale Rd. 201 Hale Rd., Manchester, CT 06042
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~43.07 miles southeast of Chesterfield
  • Includes a pool: Seasonal heated outdoor pool and hot tub
  • Affordable Suburban hotel
More Photos Pool image of Newly Remodeled Residence Inn by Marriott Hartford Manchester
From$109
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Homewood Suites by Hilton Hartford Manchester : 109 Pavilions Dr. 109 Pavilions Dr., Manchester, CT 06042
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~43.17 miles south of Chesterfield
  • Pool details: Indoor Heated Pool and Whirlpool Tub
  • Mid-scale Suburban hotel
More Photos Swimming pool at Homewood Suites by Hilton Hartford Manchester
From$99
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