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 in Hadley 24 Bay Rd., Hadley, MA 01035
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~12.62 miles east of Chesterfield
  • Includes a pool: Indoor Heated Pool open from 7am - 9pm daily. Located on the first floor just off the lobby.
  • Three Star Suburban property
More Photos Pool image of 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 available: Heated Indoor Pool open from 7am - 9pm daily.
  • 3-star Suburban hotel
More Photos Pool image of Towneplace Suites by Marriott
From$140
Average 3.0 /5 Review Score 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
  • Includes a pool: Indoor and heated pool open from 6AM to 10PM
  • 3-star Suburban property
More Photos Photo of Fairfield Inn & Suites Springfield Holyoke Pool
From$109
Very Good 4.0 /5 Reviews Call BookMore Details
Hampton Inn Chicopee / Springfield - Chicopee 600 Memorial Dr., Chicopee, MA 01020
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~20.13 miles southeast of Chesterfield
  • Pool details: Relax in our Indoor Pool open 9 AM - 10 PM.
  • 3-star Suburban property
More Photos Swimming pool at Hampton Inn Chicopee / Springfield
From$109
Very Good 4.0 /5 Hotel 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
  • Includes a pool: Indoor pool Pool Hours 6am to 11pm
  • Mid-scale Highway hotel
More Photos Photo of Residence Inn by Marriott Springfield Chicopee Pool
From$99
Very Good 4.0 /5 Reviews Call BookMore Details
TRU by Hilton Chicopee Springfield : 440 Memorial Dr. 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 hotel
More Photos Swimming pool at TRU by Hilton Chicopee Springfield
From$90
Very Good 4.0 /5 Reviews 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
  • Pool details: Indoor pool open from 6am-12am daily
  • 3 star Highway hotel
More Photos Pool image of Residence Inn by Marriott West Springfield
From$97
Very Good 4.0 /5 Review Score Call BookMore Details
Comfort Inn & Suites 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
  • Cheap Suburban property
More Photos Photo of Comfort Inn & Suites Pool
From$129
Average 3.0 /5 Reviews 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
  • Includes a pool: Covered seasonal outdoor pool Handicapped lift open 10am to 10pm
  • Two-star Suburban hotel
More Photos Photo of Quality Inn West Springfield Pool
From$75
Average 3.0 /5 Recent 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
  • Has swimming pool
  • Midscale hotel
More Photos Swimming pool at Courtyard West Spring Marriott
From$90
Very Good 4.0 /5 Guest 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
  • Pool available: Indoor heated pool & hot tub, hours: 8am - 10pm, Deep end: 5 feet
  • Three Star Suburban hotel
More Photos Photo of Holiday Inn Express Pittsfield Lenox Berkshires Pool
From$80
Average 3.0 /5 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
  • 2 star Mountain hotel
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 Photo of Hilton Garden Inn Lenox Pittsfield Pool
From$95
Very Good 4.0 /5 Latest 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
  • Includes a pool
  • Mid-scale hotel
More Photos Pool image of Best Western Springfield West Inn
From$73
Average 3.0 /5 Hotel Reviews Call BookMore Details
La Quinta by Wyndham 100 Congress St., Springfield, MA 01104
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~23.19 miles southeast of Chesterfield
  • Pool available: 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 Recent Reviews Call BookMore Details
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Holiday Inn Club Vacations Oak N Spruce Resort 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)
  • Mid-scale Mountain property
More Photos Swimming pool at Holiday Inn Club Vacations Oak N Spruce Resort
From$89
Very Good 4.0 /5 Read Reviews Call BookMore Details
Sheraton Springfield in Springfield 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
  • Three Star Downtown property
More Photos Pool image of Sheraton Springfield
From$80
Average 3.0 /5 Hotel 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
  • 3-star hotel
More Photos hotel room
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Ludlow by IHG 321 Center St., Ludlow, MA 01056
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~24.05 miles southeast of Chesterfield
  • Pool details: Heated indoor pool open 7am - 9pm daily.
  • Affordable 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 - Lanesborough 276 Brodie Mtn Rd., Lanesborough, MA 01237
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~24.55 miles west of Chesterfield
  • Has swimming 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 hotel
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. 40 Main St., North Adams, MA 01247
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~25.37 miles northwest of Chesterfield
  • Pool details: 5am-10pm Indoor
  • Midscale Downtown hotel
More Photos Photo of Hotel Downstreet Ascend Hotel Collection Pool
From$136
Very Good 4.0 /5 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
  • Pool in hotel: Outdoor heated pool open 24 hours daily year round. Sauna, outdoor hot tub and 24 hour fitness Center onsite.
  • Expensive Downtown hotel
More Photos Swimming pool at The Porches Inn at Mass Moca
From$199
Very Good 4.0 /5 Latest Reviews 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 available: Country Inn Pool is open 8a - 10p daily. Outdoor heated pool open year round.
  • Midscale Mountain property
More Photos Pool image of Jiminy Peak Mountain Resort
From$105
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Maple Terrace Motel in Williamstown 555 Main St., Williamstown, MA 01267
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~28.26 miles northwest of Chesterfield
  • Pool details: Beautiful secluded heated pool with amazing and breathtaking views. Opens Daily 9 AM and closes at Dusk.
  • Two-star Rural property
More Photos Pool image of Maple Terrace Motel
From$59
Very Good 4.0 /5 Review Score 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
  • Pool in hotel
  • 3-star Resort property
More Photos Pool image of Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi
From$109
Very Good 4.0 /5 Review Score Call BookMore Details
Hilton Garden Inn Hartford North / Bradley Intl Airport, Babc2af01bf25d1094cea9b5604bcbb1, CT 06095
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~32.24 miles south of Chesterfield
  • Has swimming pool: 5:00am- 10:00pm
  • 3-star Airport property
More Photos Swimming pool at Hilton Garden Inn
From$80
Average 3.0 /5 Hotel 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
  • Includes a pool: Small, shallow indoor pool, open 24 hours a day
  • 4-star Mountain hotel
More Photos Photo of The White House Inn Pool
From$75
Average 3.0 /5 Hotel Reviews 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.
  • Midscale Airport hotel
More Photos Photo of Holiday Inn Express & Suites Bradley Airport by IHG Pool
From$85
Very Good 4.0 /5 Read Reviews Call BookMore Details
Springhill Suites Marriott Airport 225 Ella Grasso Turnpike, Windsor Locks, CT 06096
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~32.98 miles south of Chesterfield
  • Has swimming pool: Small indoor heated pool. Not big enough for large groups of people.
  • Three Star Airport hotel
More Photos Pool image of Springhill Suites Marriott Airport
From$95
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Econo Lodge Inn & Suites Windsor Locks Bradley Airport - Windsor Locks 34 Old County Rd., Windsor Locks, CT 06096
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~33.28 miles south of Chesterfield
  • Pool available: Seasonal-Outdoor
  • Cheap Airport hotel
More Photos Pool image of Econo Lodge Inn & Suites Windsor Locks Bradley Airport
From$45
Average 3.0 /5 Latest Reviews Call BookMore Details
Econo Lodge Brattleboro South 515 Canal St., Brattleboro, VT 05301
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~33.78 miles northeast of Chesterfield
  • Pool in hotel
  • Low priced Downtown hotel
More Photos Swimming pool at Econo Lodge Brattleboro South
From$53
Not Good 1.0 /5 Hotel Reviews Call BookMore Details
Courtyard By Marriott Hartford/Windsor Airport in Windsor 1 Day Hill Rd., Windsor, CT 06095
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~34.17 miles south of Chesterfield
  • Pool in hotel
  • Three Star Downtown property
More Photos Swimming pool at Courtyard By Marriott Hartford/Windsor Airport
From$219
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Baymont by Wyndham East Windsor Bradley Airport 260 Main St., East Windsor, CT 06088
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~34.74 miles south of Chesterfield
  • Pool details: Indoor Pool/ open from 5:30AM-11:00PM
  • Affordable Suburban property
More Photos Photo of Baymont by Wyndham East Windsor Bradley Airport Pool
From$40
Average 3.0 /5 Latest 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
  • Has swimming pool: 9am - 9pm. Indoor heated pool.
  • 3 star Airport property
More Photos Photo of Ramada by Wyndham Windsor Locks Pool
From$80
Average 3.0 /5 Read 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
  • Mid-scale Suburban property
More Photos Swimming pool at 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 details: 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 Read 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
  • Pool details: Inside pool open 7am - 11pm 24 Hour Fitness Center
  • Midscale Suburban property
More Photos Photo of Marriott Hartford/Windsor Airport Pool
From$90
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Hyatt House Hartford North / Windsor : 200 Corporate Dr. 200 Corporate Dr., Windsor, CT 06095
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~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
More Photos Pool image of Hyatt House Hartford North / Windsor
From$89
Average 3.0 /5 Guest 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
  • Includes a pool: open 6am-10pm indoor heated pool. 3 foot deep to 5 foot deep
  • Low-priced Highway hotel
More Photos Pool image of Comfort Inn & Suites Brattleboro I 91
From$79
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hampton Inn Brattleboro 1378 Putney Rd., Brattleboro, VT 05301
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~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'
  • Mid-scale Rural property
More Photos Swimming pool at Hampton Inn Brattleboro
From$105
Very Good 4.0 /5 Review Score Call BookMore Details
Residence Inn by Marriott Hartford Windsor - Windsor 100 Dunfey Lane, Windsor, CT 06095
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~38.03 miles south of Chesterfield
  • Includes a pool: Outdoor pool only open Memorial Day - Labor Day 9a-9p daily.
  • 3 star Highway hotel
More Photos Swimming pool at Residence Inn by Marriott Hartford Windsor
From$96
Average 3.0 /5 Guest Reviews Call BookMore Details
Hideaway Inn Mt. Snow - Dover 270 Handle Rd., Dover, VT 05356
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~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.
  • Economy Mountain property
More Photos Pool image of Hideaway Inn Mt. Snow
From$50
Average 3.0 /5 Reviews Call BookMore Details
Best Western Bennington in Bennington 220 Northside Dr., Bennington, VT 05201
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~39.82 miles northwest of Chesterfield
  • Includes a pool: Outdoor, seasonal
  • Two-star Suburban hotel
More Photos Swimming pool at Best Western Bennington
From$36
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Residence Inn by Marriott Hartford Avon 55 Simsbury Rd., Avon, CT 06001
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~39.88 miles south of Chesterfield
  • Pool details: Seasonal outdoor swimming pool and hot tub. Hours 9:00 AM - 9:00 PM.
  • 3-star Suburban hotel
More Photos Pool image of Residence Inn by Marriott Hartford Avon
From$80
Very Good 4.0 /5 Reviews 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
  • Includes a pool: Indoor Pool is open from 7AM-10PM daily. Pool is 12,000 gallons
  • Affordable Mountain property
More Photos Photo of Hampton Inn Bennington Pool
From$80
Average 3.0 /5 Reviews Call BookMore Details
Newly Remodeled Residence Inn by Marriott Hartford Manchester in Manchester 201 Hale Rd., Manchester, CT 06042
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~43.07 miles southeast of Chesterfield
  • Pool available: Seasonal heated outdoor pool and hot tub
  • Affordable Suburban property
More Photos Photo of Newly Remodeled Residence Inn by Marriott Hartford Manchester Pool
From$109
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Homewood Suites by Hilton Hartford 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 property
More Photos Pool image of Homewood Suites by Hilton Hartford Manchester
From$99
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn Sturbridge - Sturbridge 328 Main St., Sturbridge, MA 01566
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~43.25 miles east of Chesterfield
  • We have a pool ready for use
  • 3 star Highway hotel
More Photos Photo of Hampton Inn Sturbridge Pool
From$119
Very Good 4.0 /5 Review Score Call BookMore Details
Publick House Historic Inn and Country Motor Lodge 277 Main St. (Rt 131), Sturbridge, MA 01566
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~43.53 miles east of Chesterfield
  • Has swimming pool: Outdoor Pool
  • 2 star Rural property
More Photos Pool image of Publick House Historic Inn and Country Motor Lodge
From$61
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Residence Inn by Marriott Albany East Greenbush / Tech Valley 3 Tech Valley Dr., East Greenbush, NY 12061
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~43.67 miles west of Chesterfield
  • Pool details: We have an indoor pool and a spa.
  • 3 star Suburban property
More Photos Swimming pool at Residence Inn by Marriott Albany East Greenbush / Tech Valley
From$117
Very Good 4.0 /5 Read Reviews Call BookMore Details

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