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 24 Bay Rd., Hadley, MA 01035
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~12.62 miles east of Chesterfield
  • Has swimming pool: Indoor Heated Pool open from 7am - 9pm daily. Located on the first floor just off the lobby.
  • 3 star Suburban hotel
More Photos Swimming pool at Hampton Inn Hadley Amherst Area
From$130 total
Very Good 4.0 /5 Review Score Call BookMore Details
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Towneplace Suites by Marriott : 237 Russell St. 237 Russell St., Hadley, MA 01035
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~14.02 miles east of Chesterfield
  • Pool in hotel: Heated Indoor Pool open from 7am - 9pm daily.
  • Affordable Suburban hotel
More Photos Pool image of Towneplace Suites by Marriott
From$168 total
Average 3.0 /5 Review Score Call BookMore Details
Comfort Inn & Suites Hadley Amherst : 400 Russell St. 400 Russell St., Hadley, MA 01035
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~15.18 miles east of Chesterfield
  • We have a pool
  • Affordable Downtown property
More Photos Photo of Comfort Inn & Suites Hadley Amherst Pool
From$106 total
Very Good 4.0 /5 Reviews Call BookMore Details
Courtyard by Marriott Hadley Amherst in Hadley 423 Russell St., Hadley, MA 01035
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~15.43 miles east of Chesterfield
  • Pool available: 6AM-11PM Indoor Pool & Spa
  • 3 star Downtown hotel
More Photos Photo of Courtyard by Marriott Hadley Amherst Pool
From$130 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Fairfield Inn & Suites Springfield Holyoke 229 Whiting Farms Rd., Holyoke, MA 01040
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~18.05 miles southeast of Chesterfield
  • Includes a pool: Indoor and heated pool open from 6AM to 10PM
  • Midscale Suburban property
More Photos Pool image of Fairfield Inn & Suites Springfield Holyoke
From$130 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Chicopee / Springfield in Chicopee 600 Memorial Dr., Chicopee, MA 01020
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~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$130 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Residence Inn by Marriott Springfield Chicopee 500 Memorial Dr., Chicopee, MA 01020
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~20.25 miles southeast of Chesterfield
  • Pool available: Indoor pool Pool Hours 9am to 10pm
  • Affordable Highway property
More Photos Photo of Residence Inn by Marriott Springfield Chicopee Pool
From$118 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
TRU by Hilton Chicopee Springfield - Chicopee 440 Memorial Dr., Chicopee, MA 01020
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~20.28 miles southeast of Chesterfield
  • Pool in hotel: Indoor Pool. Open 7AM-10PM daily.
  • Three Star hotel
More Photos Swimming pool at TRU by Hilton Chicopee Springfield
From$118 total
Average 3.0 /5 Review Score Call BookMore Details
Residence Inn by Marriott West Springfield in West Springfield 64 Border Way, West Springfield, MA 01089
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~20.55 miles southeast of Chesterfield
  • Pool details: Indoor pool open from 6am-12am daily
  • Affordable Highway hotel
More Photos Pool image of Residence Inn by Marriott West Springfield
From$116 total
Very Good 4.0 /5 Read Reviews Call BookMore Details
Comfort Inn & Suites in West Springfield 106 Capital Dr., West Springfield, MA 01089
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~20.81 miles southeast of Chesterfield
  • Pool details: Indoor pool and whirlpool open daily from 7am-10pm
  • 2 star Suburban property
More Photos Swimming pool at Comfort Inn & Suites
From$154 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Quality Inn West Springfield 1150 Riverdale St., West Springfield, MA 01089
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~20.86 miles southeast of Chesterfield
  • Pool available: Covered seasonal outdoor pool Handicapped lift open 10am to 10pm
  • Cheap Suburban property
More Photos Photo of Quality Inn West Springfield Pool
From$90 total
Average 3.0 /5 Review Score Call BookMore Details
Courtyard West Spring Marriott in West Springfield 885 Riverdale St., West Springfield, MA 01089
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~21.27 miles southeast of Chesterfield
  • We have a pool ready for use
  • Three Star property
More Photos Swimming pool at Courtyard West Spring Marriott
From$108 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Pittsfield Lenox Berkshires : 1055 South St. 1055 South St., Pittsfield, MA 01201
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~21.56 miles west of Chesterfield
  • Pool details: Indoor heated pool & hot tub, hours: 8am - 10pm, Deep end: 5 feet
  • Affordable Suburban property
More Photos Photo of Holiday Inn Express Pittsfield Lenox Berkshires Pool
From$96 total
Average 3.0 /5 Guest Reviews Call BookMore Details
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Berkshire Mountain Lodge - Pittsfield 8 Dan Fox Dr., Pittsfield, MA 01201
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~21.64 miles west of Chesterfield
  • Pool details: Indoor pool & hot tub Open daily 8am-11pm
  • Cheap Mountain hotel
More Photos Pool image of Berkshire Mountain Lodge
From$150 total
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield 1032 South St., Pittsfield, MA 01201
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~21.71 miles west of Chesterfield
  • Pool in hotel: Indoor heated pool/hot tub
  • 3-star Suburban hotel
More Photos Swimming pool at Hilton Garden Inn Lenox Pittsfield
From$114 total
Very Good 4.0 /5 Review Score Call BookMore Details
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Hampton Inn & Suites Lenox Berkshires : 445 Pittsfield Rd. 445 Pittsfield Rd., Lenox, MA 01240
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~21.84 miles west of Chesterfield
  • Includes a pool
  • Affordable Mountain property
More Photos Pool image of Hampton Inn & Suites Lenox Berkshires
From$96 total
Average 3.0 /5 Reviews Call BookMore Details
Best Western Springfield West Inn - West Springfield 429 Riverdale St., West Springfield, MA 01089
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~21.92 miles southeast of Chesterfield
  • Has swimming pool
  • 3 star property
More Photos Pool image of Best Western Springfield West Inn
From$87 total
Average 3.0 /5 Guest Reviews Call BookMore Details
La Quinta by Wyndham 100 Congress St., Springfield, MA 01104
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~23.19 miles southeast of Chesterfield
  • Pool 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 property
More Photos Pool image of La Quinta by Wyndham
From$96 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort : 190 Meadow St. 190 Meadow St., South Lee, MA 01260
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~23.58 miles west of Chesterfield
  • Pool available: Two outdoor pools (seasonal) Two indoor pools (hours vary) Hot Tub (hours vary)
  • 3 star Mountain property
More Photos Photo of Holiday Inn Club Vacations Oak N Spruce Resort Pool
From$106 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Sheraton Springfield Monarch Place Hotel : 1 Monarch Place 1 Monarch Place, Springfield, MA 01144
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~23.72 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
  • 3 star Downtown hotel
More Photos Swimming pool at Sheraton Springfield Monarch Place Hotel
From$96 total
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Express Springfield Downtown : 145 State St. 145 State St., Springfield, MA 01103
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~23.87 miles southeast of Chesterfield
  • Pool details: Indoor heated pool
  • Three Star hotel
More Photos hotel room
From$96 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Springfield / Downtown - Springfield 851 East Columbus Ave., Springfield, MA 01105
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~24.46 miles southeast of Chesterfield
  • Pool in hotel: 7am-10Pm
  • Midscale Downtown hotel
More Photos Photo of Hampton Inn & Suites Springfield / Downtown Pool
From$118 total
Very Good 4.0 /5 Reviews Call BookMore Details
Vacation Village in The Berkshires : 276 Brodie Mtn Rd. 276 Brodie Mtn Rd., Lanesborough, MA 01237
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~24.55 miles west of Chesterfield
  • Pool available: 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.
  • Affordable Mountain hotel
More Photos Swimming pool at Vacation Village in The Berkshires
From$90 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
The Red Lion Inn : 30 Main St. 30 Main St., Stockbridge, MA 01262
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~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!
  • 3 star Rural hotel
More Photos Photo of The Red Lion Inn Pool
From$144 total
Average 3.0 /5 Latest Reviews Call BookMore Details
The Porches Inn at Mass Moca : 231 River St. 231 River St., North Adams, MA 01247
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~25.56 miles northwest of Chesterfield
  • Includes a pool: 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$238 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Jiminy Peak Mountain Resort in Hancock 37 Corey Rd., Hancock, MA 01237
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~25.75 miles west of Chesterfield
  • Pool details: Country Inn Pool is open 8a - 10p daily. Outdoor heated pool open year round.
  • 3 star Mountain property
More Photos Pool image of Jiminy Peak Mountain Resort
From$126 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Maple Terrace Motel 555 Main St., Williamstown, MA 01267
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~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.
  • Cheap Rural hotel
More Photos Photo of Maple Terrace Motel Pool
From$70 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Springfield Enfield 1 Bright Meadow Blvd., Enfield, CT 06082
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~28.78 miles southeast of Chesterfield
  • Pool available: Seasonal Outdoor Pool- 9am-9pm
  • Mid-scale Suburban hotel
More Photos Photo of Fairfield Inn & Suites by Marriott Springfield Enfield Pool
From$94 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox / Berks 249 Stockbridge Rd., Great Barrington, MA 01230
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~28.81 miles west of Chesterfield
  • Our hotel comes with a pool
  • 3-star Resort hotel
More Photos Pool image of Fairfield Inn & Suites by Marriott Great Barrington Lenox / Berks
From$130 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hilton Garden Inn : Hartford North / Bradley Intl Airport Hartford North / Bradley Intl Airport, Babc2af01bf25d1094cea9b5604bcbb1, CT 06095
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~32.24 miles south of Chesterfield
  • Pool details: 5:00am- 10:00pm
  • Midscale Airport property
More Photos Pool image of Hilton Garden Inn
From$96 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
The White House Inn in Wilmington 178 Vt 9 East, Wilmington, VT 05363
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~32.59 miles north of Chesterfield
  • Pool available: Small, shallow indoor pool, open 24 hours a day
  • Four-star Mountain hotel
More Photos Swimming pool at The White House Inn
From$90 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Springhill Suites Marriott Airport in Windsor Locks 225 Ella Grasso Turnpike, Windsor Locks, CT 06096
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~32.98 miles south of Chesterfield
  • Has swimming pool: Small indoor heated pool. Not big enough for large groups of people.
  • 3-star Airport property
More Photos Swimming pool at Springhill Suites Marriott Airport
From$114 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Econo Lodge Inn & Suites Windsor Locks Bradley Airport in Windsor Locks 34 Old County Rd., Windsor Locks, CT 06096
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~33.28 miles south of Chesterfield
  • Includes a pool: Seasonal-Outdoor
  • Two-star Airport hotel
More Photos Pool image of Econo Lodge Inn & Suites Windsor Locks Bradley Airport
From$54 total
Average 3.0 /5 Review Score Call BookMore Details
Fairfield Inn & Suites by Marriott Hartford Airport in Windsor Locks 2 Loten Dr., Windsor Locks, CT 06096
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~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"
  • Midscale Airport property
More Photos Swimming pool at Fairfield Inn & Suites by Marriott Hartford Airport
From$114 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Homewood Suites by Hilton Windsor Locks Hartford 65 Ella Grasso Turnpike, Windsor Locks, CT 06096
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~33.76 miles south of Chesterfield
  • Pool in hotel: We offer an outside swimming pool that is open from Memorial Day weekend through Labor Day weekend. Hours of operation daily: 10am-9pm.
  • Affordable Airport hotel
More Photos Pool image of Homewood Suites by Hilton Windsor Locks Hartford
From$118 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Econo Lodge Brattleboro South - Brattleboro 515 Canal St., Brattleboro, VT 05301
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~33.78 miles northeast of Chesterfield
  • Has swimming pool
  • Inexpensive Downtown hotel
More Photos Swimming pool at Econo Lodge Brattleboro South
From$63 total
Not Good 1.0 /5 Reviews Call BookMore Details
Doubletree by Hilton Hotel Hartford Bradley Airport : 16 Ella T Grasso Turnpike 16 Ella T Grasso Turnpike, Windsor Locks, CT 06096
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~33.79 miles south of Chesterfield
  • Pool in hotel: The hotel offers an indoor heated pool. It is open from 7am-10pm daily
  • Three Star Airport property
More Photos Swimming pool at Doubletree by Hilton Hotel Hartford Bradley Airport
From$87 total
Average 3.5 /5 Guest Reviews Call BookMore Details
Courtyard By Marriott Hartford/Windsor Airport - Windsor 1 Day Hill Rd., Windsor, CT 06095
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~34.17 miles south of Chesterfield
  • With a pool!
  • Affordable Downtown property
More Photos Photo of Courtyard By Marriott Hartford/Windsor Airport Pool
From$262 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Baymont by Wyndham East Windsor Bradley Airport : 260 Main St. 260 Main St., East Windsor, CT 06088
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~34.74 miles south of Chesterfield
  • Pool in hotel: Indoor Pool/ open from 5:30AM-11:00PM
  • Mid-scale Suburban hotel
More Photos Pool image of Baymont by Wyndham East Windsor Bradley Airport
From$48 total
Average 3.0 /5 Read Reviews Call BookMore Details
Ramada by Wyndham Windsor Locks 383 South Center St., Windsor Locks, CT 06096
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~35.20 miles south of Chesterfield
  • Has swimming pool: 9am - 9pm. Indoor heated pool.
  • Mid-scale Airport property
More Photos Swimming pool at Ramada by Wyndham Windsor Locks
From$96 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express & Suites Brattleboro in Brattleboro 100 Chickering Dr., Brattleboro, VT 05301
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~36.41 miles northeast of Chesterfield
  • Pool in hotel: Indoor pool/ open 5am-11pm
  • Midscale Suburban hotel
More Photos Photo of Holiday Inn Express & Suites Brattleboro Pool
From$94 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Colonial Motel And Spa : 889 Putney Rd. 889 Putney Rd., Brattleboro, VT 05301
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~36.48 miles northeast of Chesterfield
  • Pool available: 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
  • Affordable Rural property
More Photos Photo of Colonial Motel And Spa Pool
From$70 total
Average 3.0 /5 Review Score Call BookMore Details
Black Mountain Inn : 959 Putney Rd. 959 Putney Rd., Brattleboro, VT 05301
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~36.60 miles northeast of Chesterfield
  • Pool details: Seasonal outdoor pool
  • Cheap Suburban property
More Photos Swimming pool at Black Mountain Inn
From$68 total
Average 3.5 /5 Guest Reviews Call BookMore Details
Hyatt House Hartford North / Windsor in Windsor 200 Corporate Dr., Windsor, CT 06095
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~37.07 miles south of Chesterfield
  • Pool details: Indoor heated pool and whirlpool 6 am - 9 pm *Limit four (4) guests per room
  • 3-star Suburban property
More Photos Pool image of Hyatt House Hartford North / Windsor
From$106 total
Average 3.0 /5 Read Reviews Call BookMore Details
Comfort Inn & Suites Brattleboro I 91 1186 Putney Rd., Brattleboro, VT 05301
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~37.09 miles northeast of Chesterfield
  • Pool in hotel: open 6am-10pm indoor heated pool. 3 foot deep to 5 foot deep
  • Low-priced Highway property
More Photos Pool image of Comfort Inn & Suites Brattleboro I 91
From$94 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Brattleboro - Brattleboro 1378 Putney Rd., Brattleboro, VT 05301
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~37.46 miles northeast of Chesterfield
  • Pool details: Indoor heated salt water pool and whirl pool Tub. The pool is 4' - 5'deep 15'x30'
  • Three Star Rural hotel
More Photos Photo of Hampton Inn Brattleboro Pool
From$126 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Residence Inn by Marriott Hartford Windsor - Windsor 100 Dunfey Lane, Windsor, CT 06095 Website
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~38.03 miles south of Chesterfield
  • Pool in hotel: Outdoor pool only open Memorial Day - Labor Day 9a-9p daily.
  • Three Star Highway hotel
More Photos Photo of Residence Inn by Marriott Hartford Windsor Pool
From$115 total
Average 3.0 /5 Reviews Call BookMore Details
Hotel Vervana Trademark Collection by Wyndham in Bennington 141 Main St., Bennington, VT 05201
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~38.48 miles northwest of Chesterfield
  • Pool available: Outdoor pool.
  • Mid-scale property
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From$96 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Hideaway Inn Mt. Snow 270 Handle Rd., Dover, VT 05356
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~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.
  • Low priced Mountain property
More Photos Swimming pool at Hideaway Inn Mt. Snow
From$60 total
Average 3.0 /5 Latest Reviews Call BookMore Details
Residence Inn by Marriott Hartford Avon 55 Simsbury Rd., Avon, CT 06001
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~39.88 miles south of Chesterfield
  • Pool available: Seasonal outdoor swimming pool and hot tub. Hours 9:00 AM - 9:00 PM.
  • Affordable Suburban hotel
More Photos Pool image of Residence Inn by Marriott Hartford Avon
From$96 total
Very Good 4.0 /5 Review Score Call BookMore Details

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