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
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
24 Bay Rd., Hadley, MA 01035 ~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.
  • Affordable Suburban property
More Photos Pool image of Hampton Inn Hadley Amherst Area
From$109
Very Good 4.0 /5 Latest Reviews Call BookMore Details
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Red Roof Inn Plus+ South Deerfield – Amherst
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
9 Greenfield Rd., South Deerfield, MA 01373 ~12.80 miles east of Chesterfield
  • Pool in hotel: Indoor heated pool maintained in 80-82 degrees, in a tropical environment.
  • Three Star Highway property
More Photos Swimming pool at Red Roof Inn Plus+ South Deerfield – Amherst
From$57
Average 3.0 /5 Hotel Reviews Call BookMore Details
Towneplace Suites by Marriott in Hadley
+1-800-716-8490

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237 Russell St., Hadley, MA 01035 ~14.02 miles east of Chesterfield
  • Pool details: Heated Indoor Pool open from 7am - 9pm daily.
  • Mid-scale Suburban property
More Photos Pool image of Towneplace Suites by Marriott
From$140
Average 3.0 /5 Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Springfield Holyoke - Holyoke
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
229 Whiting Farms Rd., Holyoke, MA 01040 ~18.05 miles southeast of Chesterfield
  • Pool in hotel: Indoor and heated pool open from 6AM to 10PM
  • Affordable Suburban property
More Photos Swimming pool at Fairfield Inn & Suites by Marriott Springfield Holyoke
From$109
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Chicopee / Springfield
+1-888-965-1860

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600 Memorial Dr., Chicopee, MA 01020 ~20.13 miles southeast of Chesterfield
  • Has swimming pool: Relax in our Indoor Pool open 9 AM - 10 PM.
  • Affordable 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 in Chicopee
+1-888-788-5576

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500 Memorial Dr., Chicopee, MA 01020 ~20.25 miles southeast of Chesterfield
  • Pool in hotel: Indoor pool Pool Hours 6am to 11pm
  • 3 star Highway hotel
More Photos Pool image of Residence Inn by Marriott Springfield Chicopee
From$99
Very Good 4.0 /5 Read Reviews Call BookMore Details
TRU by Hilton Chicopee Springfield in Chicopee
+1-888-897-9207

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440 Memorial Dr., Chicopee, MA 01020 ~20.29 miles southeast of Chesterfield
  • Pool in hotel: Indoor Pool. Open 7AM-10PM daily.
  • Mid-scale hotel
More Photos Photo of TRU by Hilton Chicopee Springfield Pool
From$90
Very Good 4.0 /5 Reviews Call BookMore Details
Residence Inn by Marriott West Springfield : 64 Border Way
+1-888-311-4278

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64 Border Way, West Springfield, MA 01089 ~20.55 miles southeast of Chesterfield
  • Pool in hotel: Indoor pool open from 6am-12am daily
  • Affordable Highway hotel
More Photos Swimming pool at Residence Inn by Marriott West Springfield
From$97
Very Good 4.0 /5 Read Reviews Call BookMore Details
Comfort Inn & Suites
+1-888-469-4795

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106 Capital Dr., West Springfield, MA 01089 ~20.81 miles southeast of Chesterfield
  • Pool in hotel: Indoor pool and whirlpool open daily from 7am-10pm
  • Two-star Suburban property
More Photos Pool image of Comfort Inn & Suites
From$129
Average 3.0 /5 Guest Reviews Call BookMore Details
Quality Inn West Springfield - West Springfield
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
1150 Riverdale St., West Springfield, MA 01089 ~20.86 miles southeast of Chesterfield
  • Includes a pool: Covered seasonal outdoor pool Handicapped lift open 10am to 10pm
  • 2 star Suburban property
More Photos Pool image of Quality Inn West Springfield
From$75
Average 3.0 /5 Hotel Reviews Call BookMore Details
Courtyard West Spring Marriott
+1-888-841-5292

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885 Riverdale St., West Springfield, MA 01089 ~21.27 miles southeast of Chesterfield
  • Pool in hotel
  • Three Star hotel
More Photos Swimming pool at Courtyard West Spring Marriott
From$90
Very Good 4.0 /5 Read Reviews Call BookMore Details
Berkshire Mountain Lodge in Pittsfield
+1-888-455-5160

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8 Dan Fox Dr., Pittsfield, MA 01201 ~21.64 miles west of Chesterfield
  • Has swimming pool: Indoor pool & hot tub Open daily 8am-11pm
  • Economy 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 - Pittsfield
+1-888-965-8297

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1032 South St., Pittsfield, MA 01201 ~21.71 miles west of Chesterfield
  • Includes a pool: 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 Guest Reviews Call BookMore Details
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Yankee Inn - Lenox
+1-888-906-6358

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461 Pittsfield Rd., Lenox, MA 01240 ~21.80 miles west of Chesterfield
  • Pool in hotel: Indoor - Pool
  • 2-star property
More Photos Photo of Yankee Inn Pool
From$145
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Best Western Springfield West Inn
+1-888-749-6785

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429 Riverdale St., West Springfield, MA 01089 ~21.92 miles southeast of Chesterfield
  • Includes a swimming pool
  • Affordable hotel
More Photos Pool image of Best Western Springfield West Inn
From$74
Average 3.0 /5 Guest Reviews Call BookMore Details
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La Quinta by Wyndham
+1-888-878-9982

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100 Congress St., Springfield, MA 01104 ~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.
  • 3 star Downtown property
More Photos Swimming pool at La Quinta by Wyndham
From$80
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort
+1-888-389-4485

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190 Meadow St., South Lee, MA 01260 ~23.58 miles west of Chesterfield
  • Pool in hotel: Two outdoor pools (seasonal) Two indoor pools (hours vary) Hot Tub (hours vary)
  • Mid-scale Mountain hotel
More Photos Photo of Holiday Inn Club Vacations Oak N Spruce Resort Pool
From$89
Very Good 4.0 /5 Read Reviews Call BookMore Details
Sheraton Springfield in Springfield
+1-888-389-4121

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1 Monarch Place, Springfield, MA 01144 ~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 hotel
More Photos Swimming pool at Sheraton Springfield
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Springfield Downtown in Springfield
+1-888-675-2083

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145 State St., Springfield, MA 01103 ~23.87 miles southeast of Chesterfield
  • Pool available: Indoor heated pool
  • Affordable hotel
More Photos hotel room
From$80
Average 3.0 /5 Review Score Call BookMore Details
Vacation Village in The Berkshires - Lanesborough
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
276 Brodie Mtn Rd., Lanesborough, MA 01237 ~24.55 miles west of Chesterfield
  • Pool details: 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
More Photos Swimming pool at Vacation Village in The Berkshires
From$75
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hotel Downstreet Ascend Hotel Collection - North Adams
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
40 Main St., North Adams, MA 01247 ~25.37 miles northwest of Chesterfield
  • Has swimming pool: 5am-10pm Indoor
  • 3-star Downtown property
More Photos Swimming pool at Hotel Downstreet Ascend Hotel Collection
From$136
Very Good 4.0 /5 Read Reviews Call BookMore Details
The Porches Inn at Mass Moca : 231 River St.
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
231 River St., North Adams, MA 01247 ~25.56 miles northwest of Chesterfield
  • Has swimming pool: Outdoor heated pool open 24 hours daily year round. Sauna, outdoor hot tub and 24 hour fitness Center onsite.
  • 4 star Downtown hotel
More Photos Photo of The Porches Inn at Mass Moca Pool
From$199
Very Good 4.0 /5 Read Reviews Call BookMore Details
Jiminy Peak Mountain Resort
+1-888-788-5576

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37 Corey Rd., Hancock, MA 01237 ~25.75 miles west of Chesterfield
  • Pool available: 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 Review Score Call BookMore Details
Maple Terrace Motel - Williamstown
+1-888-897-9207

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555 Main St., Williamstown, MA 01267 ~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.
  • Economy Rural hotel
More Photos Photo of Maple Terrace Motel Pool
From$59
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
The Williams Inn
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
101 Spring St., Williamstown, MA 01267 ~28.67 miles northwest of Chesterfield
  • Pool details: Indoor heated pool and hot tub.
  • High end Suburban hotel
More Photos Pool image of The Williams Inn
From$125
Average 3.0 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
249 Stockbridge Rd., Great Barrington, MA 01230 ~28.81 miles west of Chesterfield
  • Includes a swimming pool
  • Midscale Resort hotel
More Photos Photo of Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi Pool
From$109
Very Good 4.0 /5 Reviews Call BookMore Details
Hilton Garden Inn
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
Hartford North / Bradley Intl Airport, Babc2af01bf25d1094cea9b5604bcbb1, CT 06095 ~32.24 miles south of Chesterfield
  • Pool details: 5:00am- 10:00pm
  • Three Star Airport hotel
More Photos Photo of Hilton Garden Inn Pool
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
The White House Inn in Wilmington
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
178 Vt 9 East, Wilmington, VT 05363 ~32.59 miles north of Chesterfield
  • Pool available: Small, shallow indoor pool, open 24 hours a day
  • Four-star Mountain property
More Photos Photo of The White House Inn Pool
From$75
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express & Suites Bradley Airport by IHG
+1-888-455-5160

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New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
600 Spring St., Windsor Locks, CT 06096 ~32.83 miles south of Chesterfield
  • Pool available: Indoor Heated Pool open from 7am - 8pm daily. approximately 12 feet x 15 feet.
  • Mid-scale Airport hotel
More Photos Pool image of Holiday Inn Express & Suites Bradley Airport by IHG
From$85
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Springhill Suites Marriott Airport
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
225 Ella Grasso Turnpike, Windsor Locks, CT 06096 ~32.98 miles south of Chesterfield
  • Has swimming pool: Small indoor heated pool. Not big enough for large groups of people.
  • Affordable Airport hotel
More Photos Pool image of Springhill Suites Marriott Airport
From$95
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Econo Lodge Inn & Suites Airport in Windsor Locks
+1-888-906-6358

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New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
34 Old County Rd., Windsor Locks, CT 06096 ~33.28 miles south of Chesterfield
  • Pool available: Seasonal-Outdoor
  • Low-priced Airport property
More Photos Swimming pool at Econo Lodge Inn & Suites Airport
From$45
Average 3.0 /5 Review Score Call BookMore Details
Fairfield Inn & Suites Hartford Airport - Windsor Locks
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
2 Loten Dr., Windsor Locks, CT 06096 ~33.71 miles south of Chesterfield
  • Pool in hotel: Indoor Pool Open Monday - Sunday from 8am until 10pm 35 ft 10" by 17 ft 8"
  • Affordable Airport property
More Photos Swimming pool at Fairfield Inn & Suites Hartford Airport
From$95
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Econo Lodge Brattleboro in Brattleboro
+1-888-878-9982

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515 Canal St., Brattleboro, VT 05301 ~33.78 miles northeast of Chesterfield
  • Pool in hotel
  • Two-star Downtown property
More Photos Pool image of Econo Lodge Brattleboro
From$53
Not Good 1.0 /5 Guest Reviews Call BookMore Details
DoubleTree by Hilton Hartford - Bradley Airport
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
16 Ella Grasso Turnpike, Windsor Locks, CT 06096 ~33.79 miles south of Chesterfield
  • Pool in hotel: The hotel offers an indoor heated pool. It is open from 7am-10pm daily
  • Midscale Airport hotel
More Photos Photo of DoubleTree by Hilton Hartford - Bradley Airport Pool
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Courtyard By Marriott Hartford/Windsor Airport in Windsor
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
1 Day Hill Rd., Windsor, CT 06095 ~34.17 miles south of Chesterfield
  • Has swimming pool
  • 3 star Downtown property
More Photos Photo of Courtyard By Marriott Hartford/Windsor Airport Pool
From$219
Very Good 4.0 /5 Reviews Call BookMore Details
Baymont by Wyndham East Windsor Bradley Airport : 260 Main St.
+1-888-675-2083

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260 Main St., East Windsor, CT 06088 ~34.74 miles south of Chesterfield
  • Pool available: 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 Read Reviews Call BookMore Details
Holiday Inn Express & Suites Brattleboro in Brattleboro
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
100 Chickering Dr., Brattleboro, VT 05301 ~36.41 miles northeast of Chesterfield
  • Pool details: 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 & Spa
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
889 Putney Rd., Brattleboro, VT 05301 ~36.48 miles northeast of Chesterfield
  • Has swimming 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
  • Three Star Rural hotel
More Photos Photo of Colonial Motel & Spa Pool
From$59
Average 3.0 /5 Reviews Call BookMore Details
Marriott Hartford/Windsor Airport - Windsor
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
28 Day Hill Rd., Windsor, CT 06095 ~36.82 miles south of Chesterfield
  • Pool available: Inside pool open 7am - 11pm 24 Hour Fitness Center
  • Mid-scale Suburban hotel
More Photos Photo of Marriott Hartford/Windsor Airport Pool
From$90
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hyatt House Hartford North / Windsor - Windsor
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
200 Corporate Dr., Windsor, CT 06095 ~37.07 miles south of Chesterfield
  • Includes a pool: Indoor heated pool and whirlpool 6 am - 9 pm *Limit four (4) guests per room
  • Three Star Suburban hotel
More Photos Pool image of Hyatt House Hartford North / Windsor
From$89
Average 3.0 /5 Review Score Call BookMore Details
Comfort Inn & Suites Brattleboro I 91 in Brattleboro
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
1186 Putney Rd., Brattleboro, VT 05301 ~37.09 miles northeast of Chesterfield
  • Pool details: 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
Residence Inn by Marriott Hartford/Windsor
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
100 Dunfey Lane, Windsor, CT 06095 ~38.03 miles south of Chesterfield
  • Pool in hotel: Outdoor pool only open Memorial Day - Labor Day 10a-10p daily.
  • Mid-scale Highway hotel
More Photos Pool image of Residence Inn by Marriott Hartford/Windsor
From$96
Average 3.0 /5 Reviews Call BookMore Details
Mountaineer Inn - Dover
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
270 Handle Rd., Dover, VT 05356 ~39.39 miles north of Chesterfield
  • Pool in hotel: 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 Swimming pool at Mountaineer Inn
From$50
Average 3.0 /5 Guest Reviews Call BookMore Details
Best Western Bennington in Bennington
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
220 Northside Dr., Bennington, VT 05201 ~39.82 miles northwest of Chesterfield
  • Has swimming pool: Outdoor, seasonal
  • 2-star Suburban property
More Photos Pool image of Best Western Bennington
From$36
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Residence Inn by Marriott Hartford Avon
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
55 Simsbury Rd., Avon, CT 06001 ~39.88 miles south of Chesterfield
  • Pool available: Seasonal outdoor swimming pool and hot tub. Hours 9:00 AM - 9:00 PM.
  • 3-star Suburban hotel
More Photos Swimming pool at Residence Inn by Marriott Hartford Avon
From$80
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Bennington in Bennington
+1-888-455-5160

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51 Hannaford Sq., Bennington, VT 05201 ~40.57 miles northwest of Chesterfield
  • Pool details: Indoor Pool is open from 7AM-10PM daily. Pool is 12,000 gallons
  • Three Star Mountain property
More Photos Photo of Hampton Inn Bennington Pool
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Newly Remodeled Residence Inn by Marriott Hartford Manchester in Manchester
+1-888-965-8297

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201 Hale Rd., Manchester, CT 06042 ~43.07 miles southeast of Chesterfield
  • Pool details: Seasonal heated outdoor pool and hot tub
  • 3-star Suburban property
More Photos Photo of Newly Remodeled Residence Inn by Marriott Hartford Manchester Pool
From$109
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Homewood Suites by Hilton Hartford Manchester : 109 Pavilions Dr.
+1-888-906-6358

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109 Pavilions Dr., Manchester, CT 06042 ~43.17 miles south of Chesterfield
  • Has swimming pool: Indoor Heated Pool and Whirlpool Tub
  • 3-star Suburban property
More Photos Pool image of Homewood Suites by Hilton Hartford Manchester
From$99
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Publick House Historic Inn and Country Motor Lodge
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
277 Main St. (Rt 131), Sturbridge, MA 01566 ~43.53 miles east of Chesterfield
  • Pool details: Outdoor Pool
  • Cheap Rural hotel
More Photos Pool image of Publick House Historic Inn and Country Motor Lodge
From$61
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Residence Inn by Marriott Albany East Greenbush / Tech Valley in East Greenbush
+1-888-878-9982

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3 Tech Valley Dr., East Greenbush, NY 12061 ~43.67 miles west of Chesterfield
  • Has swimming pool: We have an indoor pool and a spa.
  • Three Star Suburban hotel
More Photos Pool image of Residence Inn by Marriott Albany East Greenbush / Tech Valley
From$117
Very Good 4.0 /5 Hotel Reviews Call BookMore Details

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