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

Fairfield Inn & Suites Springfield Northampton/Amherst : 115a Conz St.
+1-888-389-4121

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115a Conz St., Northampton, MA 01060 ~12.19 miles east of Chesterfield
  • With a pool!
  • Mid-scale hotel
More Photos Pool image of Fairfield Inn & Suites Springfield Northampton/Amherst
From$99
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
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Quality Inn & Suites Northampton - Amherst : 117 Conz St.
+1-888-675-2083

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117 Conz St., Northampton, MA 01060 ~12.26 miles east of Chesterfield
  • Pool details: open from 6am - 10pm Heated indoor pool 5 1/3 in depth
  • 2 star Highway hotel
More Photos Swimming pool at Quality Inn & Suites Northampton - Amherst
From$85
Average 3.0 /5 Recent Reviews Call BookMore Details
Hampton Inn Hadley Amherst Area - Hadley
+1-800-716-8490

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24 Bay Rd., Hadley, MA 01035 ~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 hotel
More Photos Pool image of Hampton Inn Hadley Amherst Area
From$109
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Towneplace Suites by Marriott
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
237 Russell St., Hadley, MA 01035 ~14.02 miles east of Chesterfield
  • Includes a pool: Heated Indoor Pool open from 7am - 9pm daily.
  • Mid-scale Suburban hotel
More Photos Photo of Towneplace Suites by Marriott Pool
From$140
Average 3.0 /5 Latest Reviews Call BookMore Details
D. Hotel Suites & Spa
+1-888-965-1860

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1 Country Club Rd., Holyoke, MA 01040 ~14.47 miles southeast of Chesterfield
  • Pool details: Relax in our heated indoor pool and whirlpool.
  • Three Star Highway hotel
More Photos Swimming pool at D. Hotel Suites & Spa
From$89
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Springfield Holyoke in Holyoke
+1-888-788-5576

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229 Whiting Farms Rd., Holyoke, MA 01040 ~18.05 miles southeast of Chesterfield
  • Has swimming pool: Indoor and heated pool open from 6AM to 10PM
  • Affordable Suburban hotel
More Photos Swimming pool at Fairfield Inn & Suites by Marriott Springfield Holyoke
From$109
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn Chicopee/Springfield - Chicopee
+1-888-897-9207

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600 Memorial Dr., Chicopee, MA 01020 ~20.13 miles southeast of Chesterfield
  • Pool details: 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 Hotel Reviews Call BookMore Details
Residence Inn by Marriott Springfield Chicopee in Chicopee
+1-888-311-4278

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500 Memorial Dr., Chicopee, MA 01020 ~20.25 miles southeast of Chesterfield
  • Includes a pool: Indoor pool Pool Hours 6am to 11pm
  • 3 star Highway property
More Photos Pool image of Residence Inn by Marriott Springfield Chicopee
From$99
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Residence Inn by Marriott West Springfield - West Springfield
+1-888-469-4795

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64 Border Way, West Springfield, MA 01089 ~20.55 miles southeast of Chesterfield
  • Pool details: Indoor pool open from 6am-12am daily
  • Midscale Highway property
More Photos Photo of Residence Inn by Marriott West Springfield Pool
From$97
Very Good 4.0 /5 Reviews Call BookMore Details
Comfort Inn & Suites in West Springfield
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
106 Capital Dr., West Springfield, MA 01089 ~20.81 miles southeast of Chesterfield
  • Pool available: Indoor pool and whirlpool open daily from 7am-10pm
  • Cheap Suburban property
More Photos Swimming pool at Comfort Inn & Suites
From$129
Average 3.0 /5 Reviews Call BookMore Details
Quality Inn West Springfield - West Springfield
+1-888-841-5292

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1150 Riverdale St., West Springfield, MA 01089 ~20.86 miles southeast of Chesterfield
  • Pool in hotel: Covered seasonal outdoor pool Handicapped lift open 10am to 10pm
  • Economical Suburban hotel
More Photos Swimming pool at Quality Inn West Springfield
From$75
Average 3.0 /5 Latest Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield - Pittsfield
+1-888-455-5160

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1032 South St., Pittsfield, MA 01201 ~21.71 miles west of Chesterfield
  • Includes a pool: Indoor heated pool/hot tub
  • 3-star Suburban hotel
More Photos Swimming pool at Hilton Garden Inn Lenox Pittsfield
From$95
Very Good 4.0 /5 Read Reviews Call BookMore Details
Yankee Inn in Lenox
+1-888-965-8297

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461 Pittsfield Rd., Lenox, MA 01240 ~21.80 miles west of Chesterfield
  • Includes a pool: Indoor - Pool
  • Economy hotel
More Photos Pool image of Yankee Inn
From$145
Very Good 4.0 /5 Guest Reviews Call BookMore Details
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Best Western Springfield West Inn : 429 Riverdale St.
+1-888-906-6358

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429 Riverdale St., West Springfield, MA 01089 ~21.92 miles southeast of Chesterfield
  • With a pool!
  • Mid-scale property
More Photos Pool image of Best Western Springfield West Inn
From$74
Average 3.0 /5 Read Reviews Call BookMore Details
La Quinta by Wyndham in Springfield
+1-888-749-6785

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100 Congress St., Springfield, MA 01104 ~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.
  • Mid-scale Downtown property
More Photos Swimming pool at La Quinta by Wyndham
From$80
Average 3.0 /5 Review Score Call BookMore Details
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Holiday Inn Club Vacations Oak N Spruce Resort : 190 Meadow St.
+1-888-878-9982

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190 Meadow St., South Lee, MA 01260 ~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 Swimming pool at Holiday Inn Club Vacations Oak N Spruce Resort
From$89
Very Good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Springfield Downtown - Springfield
+1-888-389-4485

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145 State St., Springfield, MA 01103 ~23.87 miles southeast of Chesterfield
  • Includes a pool: Indoor heated pool
  • Three Star hotel
More Photos hotel room
From$80
Average 3.0 /5 Reviews Call BookMore Details
MGM Springfield
+1-888-389-4121

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1 Mgm Way, Springfield, MA 01103 ~24.02 miles southeast of Chesterfield
  • Pool available: Outdoor Pool open 9am - 9pm, seasonally
  • Four-star Downtown hotel
More Photos Pool image of MGM Springfield
From$130
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Ludlow, an IHG Hotel
+1-888-675-2083

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321 Center St., Ludlow, MA 01056 ~24.05 miles southeast of Chesterfield
  • Pool in hotel: Heated indoor pool open 7am - 9pm daily.
  • Three Star Highway hotel
More Photos Photo of Holiday Inn Express Ludlow, an IHG Hotel Pool
From$89
Very Good 4.0 /5 Review Score Call BookMore Details
The Red Lion Inn
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
30 Main St., Stockbridge, MA 01262 ~25.25 miles west of Chesterfield
  • Pool in hotel: 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 hotel
More Photos Swimming pool at The Red Lion Inn
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
The Porches Inn at Mass Moca in North Adams
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
231 River St., North Adams, MA 01247 ~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 Guest Reviews Call BookMore Details
Club Wyndham Bentley Brook in Hancock
+1-888-965-1860

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1 Corey Rd., Hancock, MA 01237 ~25.62 miles west of Chesterfield
  • Pool in hotel: Indoor/Outdoor Pool Hot tub
  • Three Star Mountain hotel
More Photos Pool image of Club Wyndham Bentley Brook
From$90
Very Good 4.0 /5 Guest 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
  • Includes a pool: Country Inn Pool is open 8a - 10p daily. Outdoor heated pool open year round.
  • Mid-scale Mountain hotel
More Photos Photo of Jiminy Peak Mountain Resort Pool
From$105
Very Good 4.0 /5 Review Score Call BookMore Details
Maple Terrace Motel in Williamstown
+1-888-897-9207

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555 Main St., Williamstown, MA 01267 ~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 Photo of Maple Terrace Motel Pool
From$59
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
249 Stockbridge Rd., Great Barrington, MA 01230 ~28.81 miles west of Chesterfield
  • Includes a swimming pool
  • Affordable Resort hotel
More Photos Pool image of Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi
From$109
Very Good 4.0 /5 Latest Reviews Call BookMore Details
The White House Inn
+1-888-469-4795

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178 Vt 9 East, Wilmington, VT 05363 ~32.59 miles north of Chesterfield
  • Pool available: Small, shallow indoor pool, open 24 hours a day
  • Expensive Mountain hotel
More Photos Swimming pool at The White House Inn
From$75
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express & Suites Bradley Airport, an IHG Hotel
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
600 Spring St., Windsor Locks, CT 06096 ~32.83 miles south of Chesterfield
  • Includes a pool: Indoor Heated Pool open from 7am - 8pm daily. approximately 12 feet x 15 feet.
  • Midscale Airport property
More Photos Photo of Holiday Inn Express & Suites Bradley Airport, an IHG Hotel Pool
From$85
Very Good 4.0 /5 Review Score Call BookMore Details
Springhill Suites Marriott Airport - Windsor Locks
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
225 Ella Grasso Turnpike, Windsor Locks, CT 06096 ~32.98 miles south of Chesterfield
  • Pool in hotel: Small indoor heated pool. Not big enough for large groups of people.
  • 3 star Airport hotel
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 Airport - Windsor Locks
+1-888-455-5160

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34 Old County Rd., Windsor Locks, CT 06096 ~33.28 miles south of Chesterfield
  • Has swimming pool: Seasonal-Outdoor
  • Economical Airport hotel
More Photos Pool image of Econo Lodge Inn & Suites Airport
From$45
Average 3.0 /5 Review Score Call BookMore Details
Candlewood Suites Windsor Locks Bradley Arpt, an IHG Hotel
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
149 Ella Grasso Turnpike, Windsor Locks, CT 06096 ~33.29 miles south of Chesterfield
  • Includes a pool: Indoor Pool
  • Two star Airport hotel
More Photos Pool image of Candlewood Suites Windsor Locks Bradley Arpt, an IHG Hotel
From$79
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Motel 6 Windsor Locks, CT - Hartford
+1-888-906-6358

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3 National Dr., Windsor, CT 06096 ~33.39 miles south of Chesterfield
  • Includes a pool
  • Two-star hotel
More Photos Photo of Motel 6 Windsor Locks, CT - Hartford Pool
From$60
Poor 2.0 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites Hartford Airport
+1-888-749-6785

How should we direct your call?

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
  • 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 Hartford Airport Pool
From$95
Very Good 4.0 /5 Read Reviews Call BookMore Details
DoubleTree by Hilton Hartford - Bradley Airport in Windsor Locks
+1-888-878-9982

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
16 Ella Grasso Turnpike, Windsor Locks, CT 06096 ~33.79 miles south of Chesterfield
  • Pool details: The hotel offers an indoor heated pool. It is open from 7am-10pm daily
  • Three Star Airport hotel
More Photos Swimming pool at DoubleTree by Hilton Hartford - Bradley Airport
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Hartford/Airport
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
2168 Poquonock Ave., Windsor, CT 06095 ~34.04 miles south of Chesterfield
  • Includes a pool: Dive into relaxation in our indoor swimming pool. After an intense workout, soothe your sore muscles in the whirlpool. The pool area is open daily from 6:00 AM until 10:00 PM. Stay active with our state-of-the-art fitness center, open 24 hours a day. Choose from a variety of different cardio machines, free weights, medicine balls and more.
  • 3 star Airport hotel
More Photos Swimming pool at Hampton Inn Hartford/Airport
From$82
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Courtyard By Marriott Hartford/Windsor Airport
+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
  • We have a pool ready for use
  • 3 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 in East Windsor
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
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 Photo of Baymont by Wyndham East Windsor Bradley Airport Pool
From$40
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express & Suites Brattleboro : 100 Chickering Dr.
+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 in hotel: Indoor pool/ open 5am-11pm
  • 3-star Suburban property
More Photos Photo of Holiday Inn Express & Suites Brattleboro Pool
From$79
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hyatt House Hartford North / Windsor in Windsor
+1-800-805-5223

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New Reservations: +1-800-805-5223 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
  • Midscale Suburban hotel
More Photos Swimming pool at Hyatt House Hartford North / Windsor
From$89
Average 3.0 /5 Hotel Reviews Call BookMore Details
Quality Inn & Conference Center
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
1380 Putney Rd., Brattleboro, VT 05301 ~37.40 miles northeast of Chesterfield
  • Pool in hotel: Heated indoor Pool with Excercise Room. Outdoor pool. (seasonal)
  • 3-star Mountain hotel
More Photos Photo of Quality Inn & Conference Center Pool
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Brattleboro
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
1378 Putney Rd., Brattleboro, VT 05301 ~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
More Photos Photo of Hampton Inn Brattleboro Pool
From$105
Very Good 4.0 /5 Review Score Call BookMore Details
Residence Inn by Marriott Hartford / Windsor
+1-888-897-9207

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100 Dunfey Lane, Windsor, CT 06095 ~38.03 miles south of Chesterfield
  • Includes a pool: Outdoor pool only open Memorial Day - Labor Day 10a-10p daily.
  • Affordable Highway hotel
More Photos Photo of Residence Inn by Marriott Hartford / Windsor Pool
From$96
Average 3.0 /5 Guest Reviews Call BookMore Details
Mountaineer Inn
+1-888-311-4278

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270 Handle Rd., Dover, VT 05356 ~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.
  • Inexpensive Mountain property
More Photos Swimming pool at Mountaineer Inn
From$50
Average 3.0 /5 Reviews Call BookMore Details
Best Western Bennington
+1-888-469-4795

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220 Northside Dr., Bennington, VT 05201 ~39.82 miles northwest of Chesterfield
  • Pool in hotel: 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
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
55 Simsbury Rd., Avon, CT 06001 ~39.88 miles south of Chesterfield
  • Pool details: Seasonal outdoor swimming pool and hot tub. Hours 9:00 AM - 9:00 PM.
  • Affordable Suburban hotel
More Photos Photo of Residence Inn by Marriott Hartford Avon Pool
From$80
Very Good 4.0 /5 Read Reviews Call BookMore Details
Cambria Manchester South Windsor in South Windsor
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
1000 Long Leaf Lane, South Windsor, CT 06074 ~40.05 miles south of Chesterfield
  • Pool in hotel: Indoor Heated Pool
  • Midscale Suburban property
More Photos Swimming pool at Cambria Manchester South Windsor
From$89
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Bennington
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
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 hotel
More Photos Pool image of Hampton Inn Bennington
From$80
Average 3.0 /5 Reviews Call BookMore Details
Newly Remodeled Residence Inn by Marriott Hartford Manchester
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
201 Hale Rd., Manchester, CT 06042 ~43.07 miles southeast of Chesterfield
  • Pool details: Seasonal heated outdoor pool and hot tub
  • Midscale Suburban hotel
More Photos Photo of Newly Remodeled Residence Inn by Marriott Hartford Manchester Pool
From$109
Very Good 4.0 /5 Reviews Call BookMore Details
Courtyard by Marriott Hartford Manchester
+1-888-906-6358

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225 Slater St., Manchester, CT 06040 ~43.07 miles south of Chesterfield
  • With a pool!
  • Affordable Suburban hotel
More Photos Pool image of Courtyard by Marriott Hartford Manchester
From$85
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Publick House Historic Inn and Country Motor Lodge - Sturbridge
+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 in hotel: Outdoor Pool
  • Two star Rural hotel
More Photos Photo of Publick House Historic Inn and Country Motor Lodge Pool
From$61
Very Good 4.0 /5 Reviews Call BookMore Details
Residence Inn by Marriott Albany East Greenbush / Tech Valley - East Greenbush
+1-888-878-9982

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
3 Tech Valley Dr., East Greenbush, NY 12061 ~43.67 miles west of Chesterfield
  • Pool details: We have an indoor pool and a spa.
  • 3-star Suburban hotel
More Photos Pool image of Residence Inn by Marriott Albany East Greenbush / Tech Valley
From$117
Very Good 4.0 /5 Reviews Call BookMore Details

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