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 24 Bay Rd., Hadley, MA 01035
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~12.62 miles east of Chesterfield
  • Pool available: Indoor Heated Pool open from 7am - 9pm daily. Located on the first floor just off the lobby.
  • 3-star Suburban property
More Photos Swimming pool at Hampton Inn Hadley Amherst Area
From$109
Very good 4.0 /5 Guest Reviews Call BookMore Details
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Towneplace Suites by Marriott 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.
  • Affordable Suburban hotel
More Photos Photo of Towneplace Suites by Marriott Pool
From$140
Average 3.0 /5 Read 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
  • Has swimming pool: Indoor and heated pool open from 6AM to 10PM
  • Three Star Suburban property
More Photos Swimming pool at Fairfield Inn & Suites Springfield Holyoke
From$109
Very good 4.0 /5 Hotel 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.
  • 3-star Suburban hotel
More Photos Swimming pool at Hampton Inn Chicopee / Springfield
From$109
Very good 4.0 /5 Review Score Call BookMore Details
Residence Inn by Marriott Springfield Chicopee : 500 Memorial Dr. 500 Memorial Dr., Chicopee, MA 01020
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~20.25 miles southeast of Chesterfield
  • Includes a pool: Indoor pool Pool Hours 6am to 11pm
  • Mid-scale Highway property
More Photos Pool image of Residence Inn by Marriott Springfield Chicopee
From$99
Very good 4.0 /5 Reviews Call BookMore Details
TRU by Hilton Chicopee Springfield 440 Memorial Dr., Chicopee, MA 01020
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~20.29 miles southeast of Chesterfield
  • Pool in hotel: Indoor Pool. Open 7AM-10PM daily.
  • 3 star hotel
More Photos Photo of TRU by Hilton Chicopee Springfield Pool
From$90
Very good 4.0 /5 Guest Reviews Call BookMore Details
Residence Inn by Marriott West Springfield : 64 Border Way 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
  • 3 star Highway property
More Photos Swimming pool at Residence Inn by Marriott West Springfield
From$97
Very good 4.0 /5 Reviews Call BookMore Details
Comfort Inn & Suites in West Springfield 106 Capital Dr., West Springfield, MA 01089
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~20.81 miles southeast of Chesterfield
  • Pool in hotel: Indoor pool and whirlpool open daily from 7am-10pm
  • Economical Suburban hotel
More Photos Swimming pool at Comfort Inn & Suites
From$129
Average 3.0 /5 Review Score Call BookMore Details
Quality Inn West Springfield in West Springfield 1150 Riverdale St., West Springfield, MA 01089
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~20.86 miles southeast of Chesterfield
  • Pool available: Covered seasonal outdoor pool Handicapped lift open 10am to 10pm
  • Cheap Suburban hotel
More Photos Photo of Quality Inn West Springfield Pool
From$75
Average 3.0 /5 Reviews Call BookMore Details
Courtyard West Spring Marriott : 885 Riverdale St. 885 Riverdale St., West Springfield, MA 01089
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~21.27 miles southeast of Chesterfield
  • We have a pool
  • Midscale hotel
More Photos Pool image of Courtyard West Spring Marriott
From$90
Very good 4.0 /5 Latest 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
  • Includes a pool: Indoor heated pool & hot tub, hours: 8am - 10pm, Deep end: 5 feet
  • Affordable Suburban hotel
More Photos Photo of Holiday Inn Express Pittsfield Lenox Berkshires Pool
From$80
Average 3.0 /5 Review Score Call BookMore Details
Berkshire Mountain Lodge in Pittsfield 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
  • Two-star Mountain property
More Photos Pool image of Berkshire Mountain Lodge
From$125
Very good 4.5 /5 Recent Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield 1032 South St., Pittsfield, MA 01201
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~21.71 miles west of Chesterfield
  • Pool details: Indoor heated pool/hot tub
  • Midscale Suburban property
More Photos Swimming pool at Hilton Garden Inn Lenox Pittsfield
From$95
Very good 4.0 /5 Guest Reviews Call BookMore Details
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Best Western Springfield West Inn - West Springfield 429 Riverdale St., West Springfield, MA 01089
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~21.92 miles southeast of Chesterfield
  • Our hotel comes with a pool
  • Midscale property
More Photos Photo of Best Western Springfield West Inn Pool
From$73
Average 3.0 /5 Reviews Call BookMore Details
La Quinta by Wyndham - Springfield 100 Congress St., Springfield, MA 01104
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~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.
  • Midscale Downtown property
More Photos Photo of La Quinta by Wyndham Pool
From$80
Average 3.0 /5 Reviews Call BookMore Details
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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
  • Has swimming pool: Two outdoor pools (seasonal) Two indoor pools (hours vary) Hot Tub (hours vary)
  • 3 star Mountain property
More Photos Photo of Holiday Inn Club Vacations Oak N Spruce Resort Pool
From$89
Very good 4.0 /5 Reviews Call BookMore Details
Sheraton Springfield : 1 Monarch Place 1 Monarch Place, Springfield, MA 01144
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~23.71 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 property
More Photos Photo of Sheraton Springfield Pool
From$80
Average 3.0 /5 Guest 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
  • Has swimming pool: Indoor heated pool
  • 3-star property
More Photos hotel room
From$80
Average 3.0 /5 Latest 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
  • Includes a pool: Heated indoor pool open 7am - 9pm daily.
  • Midscale Highway property
More Photos Pool image of Holiday Inn Express Ludlow by IHG
From$89
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Vacation Village in The Berkshires : 276 Brodie Mtn Rd. 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.
  • Three Star Mountain property
More Photos Photo of Vacation Village in The Berkshires Pool
From$75
Very good 4.0 /5 Recent Reviews Call BookMore Details
Hotel Downstreet Ascend Hotel Collection 40 Main St., North Adams, MA 01247
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~25.37 miles northwest of Chesterfield
  • Has swimming pool: 5am-10pm Indoor
  • 3 star Downtown property
More Photos Photo of Hotel Downstreet Ascend Hotel Collection Pool
From$136
Very good 4.0 /5 Latest Reviews Call BookMore Details
The Porches Inn at Mass Moca 231 River St., North Adams, MA 01247
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~25.56 miles northwest of Chesterfield
  • Includes a pool: 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 Photo of The Porches Inn at Mass Moca Pool
From$199
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Jiminy Peak Mountain Resort : 37 Corey Rd. 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.
  • Midscale Mountain property
More Photos Swimming pool at Jiminy Peak Mountain Resort
From$105
Very good 4.0 /5 Guest Reviews Call BookMore Details
Maple Terrace Motel 555 Main St., Williamstown, MA 01267
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~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 hotel
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 : 249 Stockbridge Rd. 249 Stockbridge Rd., Great Barrington, MA 01230
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~28.81 miles west of Chesterfield
  • Has a pool!
  • Affordable Resort hotel
More Photos Photo of Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi Pool
From$109
Very good 4.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn : Hartford North / Bradley Intl Airport Hartford North / Bradley Intl Airport, Babc2af01bf25d1094cea9b5604bcbb1, CT 06095
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~32.24 miles south of Chesterfield
  • Pool details: 5:00am- 10:00pm
  • Mid-scale Airport property
More Photos Pool image of Hilton Garden Inn
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
The White House Inn 178 Vt 9 East, Wilmington, VT 05363
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~32.59 miles north of Chesterfield
  • Pool in hotel: Small, shallow indoor pool, open 24 hours a day
  • Expensive Mountain property
More Photos Photo of The White House Inn Pool
From$75
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn Express & Suites Bradley Airport by IHG 600 Spring St., Windsor Locks, CT 06096
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~32.83 miles south of Chesterfield
  • Pool in hotel: Indoor Heated Pool open from 7am - 8pm daily. approximately 12 feet x 15 feet.
  • 3-star Airport hotel
More Photos Photo of Holiday Inn Express & Suites Bradley Airport by IHG Pool
From$85
Very good 4.0 /5 Reviews Call BookMore Details
Springhill Suites Marriott Airport in Windsor Locks 225 Ella Grasso Turnpike, Windsor Locks, CT 06096
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~32.98 miles south of Chesterfield
  • Pool available: Small indoor heated pool. Not big enough for large groups of people.
  • Midscale Airport property
More Photos Photo of Springhill Suites Marriott Airport Pool
From$95
Very good 4.0 /5 Hotel 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
  • 2 star Airport hotel
More Photos Pool image of Econo Lodge Inn & Suites Windsor Locks Bradley Airport
From$45
Average 3.0 /5 Recent Reviews Call BookMore Details
Econo Lodge Brattleboro South 515 Canal St., Brattleboro, VT 05301
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~33.78 miles northeast of Chesterfield
  • Has swimming pool
  • Low Cost Downtown property
More Photos Photo of Econo Lodge Brattleboro South Pool
From$53
Terrible 1.0 /5 Hotel Reviews Call BookMore Details
Courtyard By Marriott Hartford/Windsor Airport - Windsor 1 Day Hill Rd., Windsor, CT 06095
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~34.17 miles south of Chesterfield
  • We have a pool
  • 3-star Downtown hotel
More Photos Pool image of Courtyard By Marriott Hartford/Windsor Airport
From$219
Very good 4.0 /5 Reviews Call BookMore Details
Baymont by Wyndham East Windsor Bradley Airport - East Windsor 260 Main St., East Windsor, CT 06088
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~34.74 miles south of Chesterfield
  • Pool available: Indoor Pool/ open from 5:30AM-11:00PM
  • Affordable Suburban hotel
More Photos Photo of Baymont by Wyndham East Windsor Bradley Airport Pool
From$40
Average 3.0 /5 Review Score Call BookMore Details
Ramada by Wyndham Windsor Locks in Windsor Locks 383 South Center St., Windsor Locks, CT 06096
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~35.20 miles south of Chesterfield
  • Has swimming pool: 9am - 9pm. Indoor heated pool.
  • Midscale Airport hotel
More Photos Photo of Ramada by Wyndham Windsor Locks Pool
From$80
Average 3.0 /5 Recent 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
  • Pool in hotel: Indoor pool/ open 5am-11pm
  • Affordable Suburban property
More Photos Pool image of Holiday Inn Express & Suites Brattleboro
From$79
Very good 4.0 /5 Review Score Call BookMore Details
Colonial Motel And Spa 889 Putney Rd., Brattleboro, VT 05301
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~36.48 miles northeast of Chesterfield
  • Pool in hotel: 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 hotel
More Photos Pool image of Colonial Motel And Spa
From$59
Average 3.0 /5 Reviews Call BookMore Details
Marriott Hartford/Windsor Airport - Windsor 28 Day Hill Rd., Windsor, CT 06095
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~36.82 miles south of Chesterfield
  • Pool in hotel: Inside pool open 7am - 11pm 24 Hour Fitness Center
  • Affordable Suburban property
More Photos Photo of Marriott Hartford/Windsor Airport Pool
From$90
Very good 4.0 /5 Reviews Call BookMore Details
Hyatt House Hartford North / Windsor in 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
  • Midscale Suburban hotel
More Photos Swimming pool at Hyatt House Hartford North / Windsor
From$89
Average 3.0 /5 Read Reviews Call BookMore Details
Comfort Inn & Suites Brattleboro I 91 1186 Putney Rd., Brattleboro, VT 05301
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~37.09 miles northeast of Chesterfield
  • Pool in hotel: open 6am-10pm indoor heated pool. 3 foot deep to 5 foot deep
  • Low priced Highway property
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., Brattleboro, VT 05301
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~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'
  • 3 star Rural hotel
More Photos Pool image of 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
  • Has swimming pool: Outdoor pool only open Memorial Day - Labor Day 9a-9p daily.
  • Affordable Highway property
More Photos Pool image of Residence Inn by Marriott Hartford Windsor
From$96
Average 3.0 /5 Review Score Call BookMore Details
Hideaway Inn Mt. Snow : 270 Handle Rd. 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.
  • 2-star Mountain hotel
More Photos Swimming pool at Hideaway Inn Mt. Snow
From$50
Average 3.0 /5 Read Reviews Call BookMore Details
Best Western Bennington - Bennington 220 Northside Dr., Bennington, VT 05201
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~39.82 miles northwest of Chesterfield
  • Has swimming pool: Outdoor, seasonal
  • Economy Suburban hotel
More Photos Photo of Best Western Bennington Pool
From$36
Very good 4.0 /5 Reviews Call BookMore Details
Residence Inn by Marriott Hartford Avon in Avon 55 Simsbury Rd., Avon, CT 06001
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~39.88 miles south of Chesterfield
  • Pool in hotel: Seasonal outdoor swimming pool and hot tub. Hours 9:00 AM - 9:00 PM.
  • Affordable Suburban property
More Photos Swimming pool at Residence Inn by Marriott Hartford Avon
From$80
Very good 4.0 /5 Read Reviews Call BookMore Details
Hampton Inn Bennington 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
  • 3-star Mountain property
More Photos Swimming pool at Hampton Inn Bennington
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Newly Remodeled Residence Inn by Marriott Hartford Manchester - Manchester 201 Hale Rd., Manchester, CT 06042
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~43.07 miles southeast of Chesterfield
  • Pool in hotel: Seasonal heated outdoor pool and hot tub
  • Mid-scale Suburban property
More Photos Pool image of Newly Remodeled Residence Inn by Marriott Hartford Manchester
From$109
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Homewood Suites by Hilton Hartford Manchester in Manchester 109 Pavilions Dr., Manchester, CT 06042
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~43.17 miles south of Chesterfield
  • Pool available: Indoor Heated Pool and Whirlpool Tub
  • Midscale Suburban hotel
More Photos Swimming pool at Homewood Suites by Hilton Hartford Manchester
From$99
Very good 4.0 /5 Reviews Call BookMore Details
Hampton Inn Sturbridge : 328 Main St. 328 Main St., Sturbridge, MA 01566
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~43.25 miles east of Chesterfield
  • With a pool!
  • Midscale Highway property
More Photos Swimming pool at Hampton Inn Sturbridge
From$119
Very good 4.0 /5 Latest Reviews Call BookMore Details
Publick House Historic Inn and Country Motor Lodge - Sturbridge 277 Main St. (Rt 131), Sturbridge, MA 01566
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~43.53 miles east of Chesterfield
  • Pool in hotel: Outdoor Pool
  • 2-star Rural hotel
More Photos Pool image of Publick House Historic Inn and Country Motor Lodge
From$61
Very good 4.0 /5 Latest Reviews Call BookMore Details
Interlaken Inn 74 Interlaken Rd., Lakeville, CT 06039
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~43.67 miles southwest of Chesterfield
  • Includes a pool: Seasonal Outdoor Heated Pool Open Memorial Day thru Labor Day
  • 3-star Resort hotel
More Photos Pool image of Interlaken Inn
From$179
Very good 4.0 /5 Guest Reviews Call BookMore Details

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