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
+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 +1-888-389-4121 ~12.62 miles east of Chesterfield
  • Pool details: Indoor Heated Pool open from 7am - 9pm daily. Located on the first floor just off the lobby.
  • 3 star Suburban property
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From$109
Very good 4.0 /5 Read Reviews Call BookMore Details
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 +1-888-675-2083 ~12.80 miles east of Chesterfield
  • Pool available: Indoor heated pool maintained in 80-82 degrees, in a tropical environment.
  • Midscale Highway hotel
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From$57
Average 3.0 /5 Read Reviews Call BookMore Details
Towneplace Suites by Marriott : 237 Russell St.
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
237 Russell St., Hadley, MA 01035 +1-800-716-8490 ~14.02 miles east of Chesterfield
  • Pool in hotel: Heated Indoor Pool open from 7am - 9pm daily.
  • Midscale Suburban hotel
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From$140
Average 3.0 /5 Read Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Springfield 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 +1-800-805-5223 ~18.05 miles southeast of Chesterfield
  • Pool details: Indoor and heated pool open from 6AM to 10PM
  • Affordable Suburban hotel
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From$109
Very good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn Chicopee / Springfield
+1-888-965-1860

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600 Memorial Dr., Chicopee, MA 01020 +1-888-965-1860 ~20.13 miles southeast of Chesterfield
  • Pool in hotel: Relax in our Indoor Pool open 9 AM - 10 PM.
  • Affordable Suburban property
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From$109
Very good 4.0 /5 Latest Reviews Call BookMore Details
Residence Inn by Marriott Springfield Chicopee : 500 Memorial Dr.
+1-888-788-5576

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500 Memorial Dr., Chicopee, MA 01020 +1-888-788-5576 ~20.25 miles southeast of Chesterfield
  • Includes a pool: Indoor pool Pool Hours 6am to 11pm
  • Affordable Highway hotel
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From$99
Very good 4.0 /5 Hotel 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 +1-888-897-9207 ~20.29 miles southeast of Chesterfield
  • Pool in hotel: Indoor Pool. Open 7AM-10PM daily.
  • Three Star hotel
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From$90
Very good 4.0 /5 Latest Reviews Call BookMore Details
Residence Inn by Marriott West Springfield
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
64 Border Way, West Springfield, MA 01089 +1-888-311-4278 ~20.55 miles southeast of Chesterfield
  • Pool details: Indoor pool open from 6am-12am daily
  • Affordable Highway property
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From$97
Very good 4.0 /5 Recent Reviews Call BookMore Details
Comfort Inn & Suites : 106 Capital Dr.
+1-888-469-4795

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106 Capital Dr., West Springfield, MA 01089 +1-888-469-4795 ~20.81 miles southeast of Chesterfield
  • Pool details: Indoor pool and whirlpool open daily from 7am-10pm
  • Low priced Suburban property
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From$129
Average 3.0 /5 Review Score Call BookMore Details
Quality Inn 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 +1-888-734-9421 ~20.86 miles southeast of Chesterfield
  • Pool details: Covered seasonal outdoor pool Handicapped lift open 10am to 10pm
  • Cheap Suburban property
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From$75
Average 3.0 /5 Latest Reviews Call BookMore Details
Courtyard West Spring Marriott - West Springfield
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
885 Riverdale St., West Springfield, MA 01089 +1-888-841-5292 ~21.27 miles southeast of Chesterfield
  • Our hotel comes with a pool
  • Affordable hotel
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From$90
Very good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Pittsfield Lenox Berkshires in Pittsfield
+1-888-455-5160

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1055 South St., Pittsfield, MA 01201 +1-888-455-5160 ~21.56 miles west of Chesterfield
  • Pool available: Indoor heated pool & hot tub, hours: 8am - 10pm, Deep end: 5 feet
  • Mid-scale Suburban hotel
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From$80
Average 3.0 /5 Reviews Call BookMore Details
Berkshire Mountain Lodge - Pittsfield
+1-888-965-8297

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8 Dan Fox Dr., Pittsfield, MA 01201 +1-888-965-8297 ~21.64 miles west of Chesterfield
  • Includes a pool: Indoor pool & hot tub Open daily 8am-11pm
  • Low-priced Mountain hotel
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From$125
Very good 4.5 /5 Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield
+1-888-906-6358

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1032 South St., Pittsfield, MA 01201 +1-888-906-6358 ~21.71 miles west of Chesterfield
  • Pool in hotel: Indoor heated pool/hot tub
  • Midscale Suburban property
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From$95
Very good 4.0 /5 Latest Reviews Call BookMore Details
Best Western Springfield West Inn : 429 Riverdale St.
+1-888-749-6785

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429 Riverdale St., West Springfield, MA 01089 +1-888-749-6785 ~21.92 miles southeast of Chesterfield
  • Has swimming pool
  • Affordable hotel
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From$74
Average 3.0 /5 Read Reviews Call BookMore Details
La Quinta by Wyndham : 100 Congress St.
+1-888-878-9982

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100 Congress St., Springfield, MA 01104 +1-888-878-9982 ~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.
  • 3-star Downtown hotel
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From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort in South Lee
+1-888-389-4485

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190 Meadow St., South Lee, MA 01260 +1-888-389-4485 ~23.58 miles west of Chesterfield
  • Pool details: Two outdoor pools (seasonal) Two indoor pools (hours vary) Hot Tub (hours vary)
  • Mid-scale Mountain hotel
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From$89
Very good 4.0 /5 Review Score Call BookMore Details
Sheraton Springfield - Springfield
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
1 Monarch Place, Springfield, MA 01144 +1-888-389-4121 ~23.71 miles southeast of Chesterfield
  • Pool details: We have an indoor pool with an outdoor patio area. Weekday Hours: 5:30am-10pm Saturday Hours: 8am-10pm Sunday Hours: 8am-8pm
  • Affordable Downtown property
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From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Springfield Downtown
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
145 State St., Springfield, MA 01103 +1-888-675-2083 ~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 Review Score Call BookMore Details
Holiday Inn Express Ludlow by IHG
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
321 Center St., Ludlow, MA 01056 +1-800-716-8490 ~24.05 miles southeast of Chesterfield
  • Has swimming pool: Heated indoor pool open 7am - 9pm daily.
  • Affordable Highway hotel
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From$89
Very good 4.0 /5 Latest Reviews Call BookMore Details
Vacation Village in The Berkshires in Lanesborough
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
276 Brodie Mtn Rd., Lanesborough, MA 01237 +1-800-805-5223 ~24.55 miles west of Chesterfield
  • Pool in hotel: 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.
  • Mid-scale Mountain property
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From$75
Very good 4.0 /5 Guest Reviews Call BookMore Details
Hotel Downstreet Ascend Hotel Collection
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
40 Main St., North Adams, MA 01247 +1-888-965-1860 ~25.37 miles northwest of Chesterfield
  • Includes a pool: 5am-10pm Indoor
  • Midscale Downtown hotel
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From$136
Very good 4.0 /5 Recent Reviews Call BookMore Details
The Porches Inn at Mass Moca : 231 River St.
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
231 River St., North Adams, MA 01247 +1-888-788-5576 ~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.
  • 4-star Downtown hotel
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From$199
Very good 4.0 /5 Reviews Call BookMore Details
Jiminy Peak Mountain Resort
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
37 Corey Rd., Hancock, MA 01237 +1-888-897-9207 ~25.75 miles west of Chesterfield
  • Pool details: Country Inn Pool is open 8a - 10p daily. Outdoor heated pool open year round.
  • Affordable Mountain hotel
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From$105
Very good 4.0 /5 Guest Reviews Call BookMore Details
Maple Terrace Motel : 555 Main St.
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
555 Main St., Williamstown, MA 01267 +1-888-311-4278 ~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
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From$59
Very good 4.0 /5 Hotel 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 +1-888-469-4795 ~28.81 miles west of Chesterfield
  • Includes a swimming pool
  • 3 star Resort hotel
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From$109
Very good 4.0 /5 Review Score Call BookMore Details
Hilton Garden Inn : Hartford North / Bradley Intl Airport
+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 +1-888-734-9421 ~32.24 miles south of Chesterfield
  • Pool available: 5:00am- 10:00pm
  • Three Star Airport hotel
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From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
The White House Inn : 178 Vt 9 East
+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 +1-888-841-5292 ~32.59 miles north of Chesterfield
  • Pool details: Small, shallow indoor pool, open 24 hours a day
  • 4-star Mountain hotel
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From$75
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express & Suites Bradley Airport by IHG in Windsor Locks
+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 +1-888-455-5160 ~32.83 miles south of Chesterfield
  • Includes a pool: Indoor Heated Pool open from 7am - 8pm daily. approximately 12 feet x 15 feet.
  • Mid-scale Airport hotel
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From$85
Very good 4.0 /5 Read 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 +1-888-965-8297 ~32.98 miles south of Chesterfield
  • Includes a pool: Small indoor heated pool. Not big enough for large groups of people.
  • Midscale Airport property
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From$95
Very good 4.0 /5 Review Score Call BookMore Details
Econo Lodge Inn & Suites Windsor Locks Bradley Airport
+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 +1-888-906-6358 ~33.28 miles south of Chesterfield
  • Pool in hotel: Seasonal-Outdoor
  • Inexpensive Airport property
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From$45
Average 3.0 /5 Read Reviews Call BookMore Details
Econo Lodge Brattleboro - Brattleboro
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
515 Canal St., Brattleboro, VT 05301 +1-888-749-6785 ~33.78 miles northeast of Chesterfield
  • We have a pool
  • 2-star Downtown property
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From$53
Terrible 1.0 /5 Read Reviews Call BookMore Details
Courtyard By Marriott Hartford/Windsor Airport - Windsor
+1-888-878-9982

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
1 Day Hill Rd., Windsor, CT 06095 +1-888-878-9982 ~34.17 miles south of Chesterfield
  • Has a pool!
  • 3 star Downtown property
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From$219
Very good 4.0 /5 Reviews Call BookMore Details
Baymont by Wyndham East Windsor Bradley Airport in East Windsor
+1-888-389-4485

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New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
260 Main St., East Windsor, CT 06088 +1-888-389-4485 ~34.74 miles south of Chesterfield
  • Has swimming pool: Indoor Pool/ open from 5:30AM-11:00PM
  • Affordable Suburban hotel
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From$40
Average 3.0 /5 Review Score Call BookMore Details
Ramada by Wyndham Windsor Locks - Windsor Locks
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
383 South Center St., Windsor Locks, CT 06096 +1-888-389-4121 ~35.20 miles south of Chesterfield
  • Includes a pool: 9am - 9pm. Indoor heated pool.
  • Midscale Airport property
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express & Suites Brattleboro
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
100 Chickering Dr., Brattleboro, VT 05301 +1-888-675-2083 ~36.41 miles northeast of Chesterfield
  • Pool details: Indoor pool/ open 5am-11pm
  • 3 star Suburban property
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From$79
Very good 4.0 /5 Reviews Call BookMore Details
Colonial Motel And Spa : 889 Putney Rd.
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
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 Review Score Call BookMore Details
Marriott Hartford/Windsor Airport : 28 Day Hill Rd.
+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
  • Has swimming pool: Inside pool open 7am - 11pm 24 Hour Fitness Center
  • Mid-scale Suburban property
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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

How should we direct your call?

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
  • Has swimming pool: Indoor heated pool and whirlpool 6 am - 9 pm *Limit four (4) guests per room
  • Mid-scale Suburban hotel
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From$89
Average 3.0 /5 Hotel Reviews Call BookMore Details
Comfort Inn & Suites Brattleboro I 91 - Brattleboro
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
1186 Putney Rd., Brattleboro, VT 05301 +1-888-788-5576 ~37.09 miles northeast of Chesterfield
  • Includes a pool: open 6am-10pm indoor heated pool. 3 foot deep to 5 foot deep
  • Low Cost Highway hotel
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From$79
Very good 4.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Brattleboro in Brattleboro
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
1378 Putney Rd., Brattleboro, VT 05301 +1-888-897-9207 ~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'
  • Three Star Rural property
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From$105
Very good 4.0 /5 Recent Reviews Call BookMore Details
Residence Inn by Marriott Hartford Windsor : 100 Dunfey Lane
+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 +1-888-311-4278 ~38.03 miles south of Chesterfield
  • Includes a pool: Outdoor pool only open Memorial Day - Labor Day 10a-10p daily.
  • Affordable Highway hotel
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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 +1-888-469-4795 ~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.
  • Two star Mountain property
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From$50
Average 3.0 /5 Reviews Call BookMore Details
Best Western Bennington - 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 +1-888-734-9421 ~39.82 miles northwest of Chesterfield
  • Includes a pool: Outdoor, seasonal
  • Cheap Suburban hotel
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From$36
Very good 4.0 /5 Recent Reviews Call BookMore Details
Residence Inn by Marriott Hartford Avon in 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 +1-888-841-5292 ~39.88 miles south of Chesterfield
  • Has swimming pool: 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 Recent Reviews Call BookMore Details
Hampton Inn Bennington : 51 Hannaford Sq.
+1-888-455-5160

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New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
51 Hannaford Sq., Bennington, VT 05201 +1-888-455-5160 ~40.57 miles northwest of Chesterfield
  • Has swimming pool: Indoor Pool is open from 7AM-10PM daily. Pool is 12,000 gallons
  • Affordable Mountain property
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From$80
Average 3.0 /5 Review Score 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 +1-888-965-8297 ~43.07 miles southeast of Chesterfield
  • Pool in hotel: Seasonal heated outdoor pool and hot tub
  • Midscale Suburban hotel
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From$109
Very good 4.0 /5 Read Reviews Call BookMore Details
Homewood Suites by Hilton Hartford Manchester
+1-888-906-6358

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109 Pavilions Dr., Manchester, CT 06042 +1-888-906-6358 ~43.17 miles south of Chesterfield
  • Has swimming pool: Indoor Heated Pool and Whirlpool Tub
  • Mid-scale Suburban hotel
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From$99
Very good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn Sturbridge
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
328 Main St., Sturbridge, MA 01566 +1-888-749-6785 ~43.25 miles east of Chesterfield
  • Has a pool!
  • Three Star Highway property
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From$119
Very good 4.0 /5 Recent Reviews Call BookMore Details
Publick House Historic Inn and Country Motor Lodge
+1-888-878-9982

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277 Main St. (Rt 131), Sturbridge, MA 01566 +1-888-878-9982 ~43.53 miles east of Chesterfield
  • Pool in hotel: Outdoor Pool
  • Low-priced Rural property
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From$61
Very good 4.0 /5 Guest Reviews Call BookMore Details
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