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.

Chesterfield Hotels with Outdoor or Indoor Pools

Hampton Inn Hadley Amherst Area : 24 Bay Rd.
+1-888-389-4121

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24 Bay Rd., Hadley, MA 01035 +1-888-389-4121 ~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 property
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From$109
Very Good 4.0 /5 Reviews Call BookMore Details
Towneplace Suites by Marriott - Hadley
+1-888-675-2083

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237 Russell St., Hadley, MA 01035 +1-888-675-2083 ~14.02 miles east of Chesterfield
  • Has swimming pool: Heated Indoor Pool open from 7am - 9pm daily.
  • Three Star Suburban hotel
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From$140
Average 3.0 /5 Read Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Springfield Holyoke - Holyoke
+1-800-716-8490

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229 Whiting Farms Rd., Holyoke, MA 01040 +1-800-716-8490 ~18.05 miles southeast of Chesterfield
  • Pool details: Indoor and heated pool open from 6AM to 10PM
  • Affordable Suburban property
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From$109
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn Chicopee / Springfield in Chicopee
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
600 Memorial Dr., Chicopee, MA 01020 +1-800-805-5223 ~20.13 miles southeast of Chesterfield
  • Pool details: Relax in our Indoor Pool open 9 AM - 10 PM.
  • Three Star Suburban hotel
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From$109
Very Good 4.0 /5 Read Reviews Call BookMore Details
Residence Inn by Marriott Springfield Chicopee - Chicopee
+1-888-965-1860

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500 Memorial Dr., Chicopee, MA 01020 +1-888-965-1860 ~20.25 miles southeast of Chesterfield
  • Pool in hotel: Indoor pool Pool Hours 6am to 11pm
  • Affordable Highway hotel
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From$99
Very Good 4.0 /5 Guest Reviews Call BookMore Details
TRU by Hilton Chicopee Springfield
+1-888-788-5576

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440 Memorial Dr., Chicopee, MA 01020 +1-888-788-5576 ~20.29 miles southeast of Chesterfield
  • Pool in hotel: Indoor Pool. Open 7AM-10PM daily.
  • Mid-scale hotel
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From$90
Very Good 4.0 /5 Review Score Call BookMore Details
Residence Inn by Marriott West Springfield - West Springfield
+1-888-897-9207

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64 Border Way, West Springfield, MA 01089 +1-888-897-9207 ~20.55 miles southeast of Chesterfield
  • Includes a pool: Indoor pool open from 6am-12am daily
  • 3-star Highway property
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From$97
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Comfort Inn & Suites
+1-888-311-4278

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106 Capital Dr., West Springfield, MA 01089 +1-888-311-4278 ~20.81 miles southeast of Chesterfield
  • Has swimming pool: Indoor pool and whirlpool open daily from 7am-10pm
  • 2-star Suburban hotel
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From$129
Average 3.0 /5 Latest Reviews Call BookMore Details
Quality Inn West Springfield : 1150 Riverdale St.
+1-888-469-4795

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1150 Riverdale St., West Springfield, MA 01089 +1-888-469-4795 ~20.86 miles southeast of Chesterfield
  • Pool in hotel: Covered seasonal outdoor pool Handicapped lift open 10am to 10pm
  • Cheap Suburban hotel
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From$75
Average 3.0 /5 Read Reviews Call BookMore Details
Berkshire Mountain Lodge in Pittsfield
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
8 Dan Fox Dr., Pittsfield, MA 01201 +1-888-734-9421 ~21.64 miles west of Chesterfield
  • Pool in hotel: Indoor pool & hot tub Open daily 8am-11pm
  • Two-star Mountain property
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From$125
Very Good 4.5 /5 Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield
+1-888-841-5292

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1032 South St., Pittsfield, MA 01201 +1-888-841-5292 ~21.71 miles west of Chesterfield
  • Has swimming pool: Indoor heated pool/hot tub
  • Affordable Suburban property
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From$95
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Yankee Inn
+1-888-455-5160

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461 Pittsfield Rd., Lenox, MA 01240 +1-888-455-5160 ~21.80 miles west of Chesterfield
  • Has swimming pool: Indoor - Pool
  • Cheap hotel
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From$145
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Best Western Springfield West Inn
+1-888-965-8297

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429 Riverdale St., West Springfield, MA 01089 +1-888-965-8297 ~21.92 miles southeast of Chesterfield
  • With a pool!
  • 3 star property
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From$74
Average 3.0 /5 Latest Reviews Call BookMore Details
La Quinta by Wyndham
+1-888-906-6358

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100 Congress St., Springfield, MA 01104 +1-888-906-6358 ~23.19 miles southeast of Chesterfield
  • Pool details: Heated indoor pool open daily 7am - 9pm. Located just off the lobby on the first floor next to the small arcade.
  • 3 star Downtown hotel
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From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort
+1-888-749-6785

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190 Meadow St., South Lee, MA 01260 +1-888-749-6785 ~23.58 miles west of Chesterfield
  • Pool in hotel: Two outdoor pools (seasonal) Two indoor pools (hours vary) Hot Tub (hours vary)
  • Three Star Mountain property
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From$89
Very Good 4.0 /5 Reviews Call BookMore Details
Sheraton Springfield : 1 Monarch Place
+1-888-878-9982

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1 Monarch Place, Springfield, MA 01144 +1-888-878-9982 ~23.71 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
  • Three Star Downtown hotel
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From$80
Average 3.0 /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 +1-888-389-4485 ~23.87 miles southeast of Chesterfield
  • Has swimming pool: Indoor heated pool
  • 3 star property
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From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Vacation Village in The Berkshires
+1-888-389-4121

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276 Brodie Mtn Rd., Lanesborough, MA 01237 +1-888-389-4121 ~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 hotel
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From$75
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Hotel Downstreet Ascend Hotel Collection : 40 Main St.
+1-888-675-2083

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40 Main St., North Adams, MA 01247 +1-888-675-2083 ~25.37 miles northwest of Chesterfield
  • Pool in hotel: 5am-10pm Indoor
  • Affordable Downtown property
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From$136
Very Good 4.0 /5 Guest Reviews Call BookMore Details
The Porches Inn at Mass Moca
+1-800-716-8490

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231 River St., North Adams, MA 01247 +1-800-716-8490 ~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.
  • High end Downtown property
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From$199
Very Good 4.0 /5 Reviews Call BookMore Details
Jiminy Peak Mountain Resort
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
37 Corey Rd., Hancock, MA 01237 +1-800-805-5223 ~25.75 miles west of Chesterfield
  • Pool details: Country Inn Pool is open 8a - 10p daily. Outdoor heated pool open year round.
  • Mid-scale Mountain property
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From$105
Very Good 4.0 /5 Reviews Call BookMore Details
Maple Terrace Motel in Williamstown
+1-888-965-1860

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555 Main St., Williamstown, MA 01267 +1-888-965-1860 ~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.
  • Economical Rural hotel
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From$59
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi in Great Barrington
+1-888-788-5576

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249 Stockbridge Rd., Great Barrington, MA 01230 +1-888-788-5576 ~28.81 miles west of Chesterfield
  • Includes a swimming pool
  • 3 star Resort property
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From$109
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn
+1-888-897-9207

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Hartford North / Bradley Intl Airport, Babc2af01bf25d1094cea9b5604bcbb1, CT 06095 +1-888-897-9207 ~32.24 miles south of Chesterfield
  • Pool available: 5:00am- 10:00pm
  • Midscale Airport property
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From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
The White House Inn - Wilmington
+1-888-311-4278

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178 Vt 9 East, Wilmington, VT 05363 +1-888-311-4278 ~32.59 miles north of Chesterfield
  • Has swimming pool: Small, shallow indoor pool, open 24 hours a day
  • Expensive Mountain property
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From$75
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express & Suites Bradley Airport by IHG - Windsor Locks
+1-888-469-4795

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600 Spring St., Windsor Locks, CT 06096 +1-888-469-4795 ~32.83 miles south of Chesterfield
  • Includes a pool: Indoor Heated Pool open from 7am - 8pm daily. approximately 12 feet x 15 feet.
  • 3 star Airport hotel
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From$85
Very Good 4.0 /5 Read Reviews Call BookMore Details
Springhill Suites Marriott Airport
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
225 Ella Grasso Turnpike, Windsor Locks, CT 06096 +1-888-734-9421 ~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
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From$95
Very Good 4.0 /5 Read Reviews Call BookMore Details
Econo Lodge Inn & Suites Airport
+1-888-841-5292

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34 Old County Rd., Windsor Locks, CT 06096 +1-888-841-5292 ~33.28 miles south of Chesterfield
  • Has swimming pool: Seasonal-Outdoor
  • Economy Airport hotel
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From$45
Average 3.0 /5 Hotel Reviews Call BookMore Details
Candlewood Suites Windsor Locks Bradley Arpt by IHG
+1-888-455-5160

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149 Ella Grasso Turnpike, Windsor Locks, CT 06096 +1-888-455-5160 ~33.29 miles south of Chesterfield
  • Pool details: Indoor Pool
  • Cheap Airport property
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From$79
Very Good 4.0 /5 Review Score Call BookMore Details
Fairfield Inn & Suites Hartford Airport
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
2 Loten Dr., Windsor Locks, CT 06096 +1-888-965-8297 ~33.71 miles south of Chesterfield
  • Pool details: Indoor Pool Open Monday - Sunday from 8am until 10pm 35 ft 10" by 17 ft 8"
  • 3 star Airport property
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From$95
Very Good 4.0 /5 Review Score Call BookMore Details
Econo Lodge Brattleboro in Brattleboro
+1-888-906-6358

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515 Canal St., Brattleboro, VT 05301 +1-888-906-6358 ~33.78 miles northeast of Chesterfield
  • Has swimming pool
  • Economical Downtown hotel
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From$53
Not Good 1.0 /5 Guest Reviews Call BookMore Details
DoubleTree by Hilton Hartford - Bradley Airport : 16 Ella Grasso Turnpike
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
16 Ella Grasso Turnpike, Windsor Locks, CT 06096 +1-888-749-6785 ~33.79 miles south of Chesterfield
  • Pool available: The hotel offers an indoor heated pool. It is open from 7am-10pm daily
  • Three Star Airport hotel
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Hartford/Airport
+1-888-878-9982

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
2168 Poquonock Ave., Windsor, CT 06095 +1-888-878-9982 ~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 property
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From$82
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Courtyard By Marriott Hartford/Windsor Airport : 1 Day Hill Rd.
+1-888-389-4485

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1 Day Hill Rd., Windsor, CT 06095 +1-888-389-4485 ~34.17 miles south of Chesterfield
  • With a pool!
  • Affordable Downtown hotel
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From$219
Very Good 4.0 /5 Read Reviews Call BookMore Details
Baymont by Wyndham East Windsor Bradley Airport in East Windsor
+1-888-389-4121

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260 Main St., East Windsor, CT 06088 +1-888-389-4121 ~34.74 miles south of Chesterfield
  • Has swimming pool: Indoor Pool/ open from 5:30AM-11:00PM
  • 3 star Suburban hotel
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From$40
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express & Suites Brattleboro
+1-888-675-2083

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100 Chickering Dr., Brattleboro, VT 05301 +1-888-675-2083 ~36.41 miles northeast of Chesterfield
  • Pool in hotel: Indoor pool/ open 5am-11pm
  • Mid-scale Suburban hotel
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From$79
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Colonial Motel & Spa
+1-800-716-8490

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889 Putney Rd., Brattleboro, VT 05301 +1-800-716-8490 ~36.48 miles northeast of Chesterfield
  • Includes a 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
  • 3-star Rural hotel
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From$59
Average 3.0 /5 Hotel Reviews Call BookMore Details
Marriott Hartford/Windsor Airport
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
28 Day Hill Rd., Windsor, CT 06095 +1-800-805-5223 ~36.82 miles south of Chesterfield
  • Pool details: Inside pool open 7am - 11pm 24 Hour Fitness Center
  • Affordable Suburban hotel
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From$90
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hyatt House Hartford North / Windsor
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
200 Corporate Dr., Windsor, CT 06095 +1-888-965-1860 ~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 property
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From$89
Average 3.0 /5 Reviews Call BookMore Details
Comfort Inn & Suites Brattleboro I 91
+1-888-788-5576

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1186 Putney Rd., Brattleboro, VT 05301 +1-888-788-5576 ~37.09 miles northeast of Chesterfield
  • Pool in hotel: open 6am-10pm indoor heated pool. 3 foot deep to 5 foot deep
  • Low Cost Highway property
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From$79
Very Good 4.0 /5 Read Reviews Call BookMore Details
Residence Inn by Marriott Hartford/Windsor
+1-888-897-9207

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100 Dunfey Lane, Windsor, CT 06095 +1-888-897-9207 ~38.03 miles south of Chesterfield
  • Has swimming pool: Outdoor pool only open Memorial Day - Labor Day 10a-10p daily.
  • Mid-scale Highway property
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From$96
Average 3.0 /5 Guest Reviews Call BookMore Details
Mountaineer Inn
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
270 Handle Rd., Dover, VT 05356 +1-888-311-4278 ~39.39 miles north of Chesterfield
  • Pool available: Heated Outdoor Pool: Open seasonally from late-May to mid-October, from 9:00 a.m. to 9:00 p.m.
  • Low priced Mountain hotel
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From$50
Average 3.0 /5 Recent Reviews Call BookMore Details
Best Western Bennington - Bennington
+1-888-469-4795

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220 Northside Dr., Bennington, VT 05201 +1-888-469-4795 ~39.82 miles northwest of Chesterfield
  • Pool available: Outdoor, seasonal
  • Low-priced Suburban property
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From$36
Very Good 4.0 /5 Read 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 +1-888-734-9421 ~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
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From$80
Very Good 4.0 /5 Reviews Call BookMore Details
Hampton Inn Bennington - Bennington
+1-888-841-5292

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51 Hannaford Sq., Bennington, VT 05201 +1-888-841-5292 ~40.57 miles northwest of Chesterfield
  • Includes a pool: Indoor Pool is open from 7AM-10PM daily. Pool is 12,000 gallons
  • Affordable Mountain hotel
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From$80
Average 3.0 /5 Review Score Call BookMore Details
Newly Remodeled Residence Inn by Marriott Hartford Manchester in Manchester
+1-888-455-5160

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201 Hale Rd., Manchester, CT 06042 +1-888-455-5160 ~43.07 miles southeast of Chesterfield
  • Includes a pool: Seasonal heated outdoor pool and hot tub
  • 3-star Suburban hotel
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From$109
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Homewood Suites by Hilton Hartford Manchester
+1-888-965-8297

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109 Pavilions Dr., Manchester, CT 06042 +1-888-965-8297 ~43.17 miles south of Chesterfield
  • Has swimming pool: Indoor Heated Pool and Whirlpool Tub
  • Three Star Suburban hotel
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From$99
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Publick House Historic Inn and Country Motor Lodge
+1-888-906-6358

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277 Main St. (Rt 131), Sturbridge, MA 01566 +1-888-906-6358 ~43.53 miles east of Chesterfield
  • Includes a pool: Outdoor Pool
  • 2-star Rural property
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From$61
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Residence Inn by Marriott Albany East Greenbush / Tech Valley : 3 Tech Valley Dr.
+1-888-749-6785

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3 Tech Valley Dr., East Greenbush, NY 12061 +1-888-749-6785 ~43.67 miles west of Chesterfield
  • Includes a pool: We have an indoor pool and a spa.
  • Midscale Suburban hotel
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From$117
Very Good 4.0 /5 Review Score Call BookMore Details
Comfort Inn & Suites Sturbridge in Sturbridge
+1-888-878-9982

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83 Hall Rd., Sturbridge, MA 01566 +1-888-878-9982 ~43.81 miles east of Chesterfield
  • Pool in hotel: Indoor Heated Pool Open 8:00AM to 10:00PM Daily. Seasonal Outdoor pool and Patio - open 8:00am to 10:00PM Daily.
  • Midscale Suburban property
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From$132
Very Good 4.0 /5 Guest Reviews Call BookMore Details
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