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Chesterfield Hotels with Outdoor or Indoor Pools

Hampton Inn Hadley Amherst Area : 24 Bay Rd.
+1-888-389-4121
24 Bay Rd., Hadley, MA 01035 ~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.
  • Three Star Suburban hotel
From$109
Very good 4.0 /5 Hotel Reviews Call BookMore Details
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Red Roof Inn Plus+ South Deerfield – Amherst
+1-888-675-2083
9 Greenfield Rd., South Deerfield, MA 01373 ~12.80 miles east of Chesterfield
  • Includes a pool: Indoor heated pool maintained in 80-82 degrees, in a tropical environment.
  • 3-star Highway property
From$57
Average 3.0 /5 Hotel Reviews Call BookMore Details
Towneplace Suites by Marriott - Hadley
+1-800-716-8490
237 Russell St., Hadley, MA 01035 ~14.02 miles east of Chesterfield
  • Pool available: Heated Indoor Pool open from 7am - 9pm daily.
  • Three Star Suburban property
From$140
Average 3.0 /5 Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Springfield Holyoke : 229 Whiting Farms Rd.
+1-800-805-5223
229 Whiting Farms Rd., Holyoke, MA 01040 ~18.05 miles southeast of Chesterfield
  • Pool details: Indoor and heated pool open from 6AM to 10PM
  • Midscale Suburban hotel
From$109
Very good 4.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Chicopee / Springfield - Chicopee
+1-888-965-1860
600 Memorial Dr., Chicopee, MA 01020 ~20.13 miles southeast of Chesterfield
  • Pool in hotel: Relax in our Indoor Pool open 9 AM - 10 PM.
  • 3 star Suburban property
From$109
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Residence Inn by Marriott Springfield Chicopee in Chicopee
+1-888-788-5576
500 Memorial Dr., Chicopee, MA 01020 ~20.25 miles southeast of Chesterfield
  • Pool available: Indoor pool Pool Hours 6am to 11pm
  • Three Star Highway hotel
From$99
Very good 4.0 /5 Recent Reviews Call BookMore Details
TRU by Hilton Chicopee Springfield - Chicopee
+1-888-897-9207
440 Memorial Dr., Chicopee, MA 01020 ~20.29 miles southeast of Chesterfield
  • Pool details: Indoor Pool. Open 7AM-10PM daily.
  • Affordable hotel
From$90
Very good 4.0 /5 Latest Reviews Call BookMore Details
Residence Inn by Marriott West Springfield
+1-888-311-4278
64 Border Way, West Springfield, MA 01089 ~20.55 miles southeast of Chesterfield
  • Pool details: Indoor pool open from 6am-12am daily
  • Mid-scale Highway hotel
From$97
Very good 4.0 /5 Guest Reviews Call BookMore Details
Comfort Inn & Suites
+1-888-469-4795
106 Capital Dr., West Springfield, MA 01089 ~20.81 miles southeast of Chesterfield
  • Pool available: Indoor pool and whirlpool open daily from 7am-10pm
  • Economy Suburban hotel
From$129
Average 3.0 /5 Read Reviews Call BookMore Details
Quality Inn West Springfield
+1-888-734-9421
1150 Riverdale St., West Springfield, MA 01089 ~20.86 miles southeast of Chesterfield
  • Pool details: Covered seasonal outdoor pool Handicapped lift open 10am to 10pm
  • 2 star Suburban hotel
From$75
Average 3.0 /5 Hotel Reviews Call BookMore Details
Courtyard West Spring Marriott
+1-888-841-5292
885 Riverdale St., West Springfield, MA 01089 ~21.27 miles southeast of Chesterfield
  • Pool in hotel
  • 3 star property
From$90
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Berkshire Mountain Lodge - Pittsfield
+1-888-455-5160
8 Dan Fox Dr., Pittsfield, MA 01201 ~21.64 miles west of Chesterfield
  • Includes a pool: Indoor pool & hot tub Open daily 8am-11pm
  • Inexpensive Mountain property
From$125
Very good 4.5 /5 Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield
+1-888-965-8297
1032 South St., Pittsfield, MA 01201 ~21.71 miles west of Chesterfield
  • Pool available: Indoor heated pool/hot tub
  • Midscale Suburban property
From$95
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Best Western Springfield West Inn in West Springfield
+1-888-906-6358
429 Riverdale St., West Springfield, MA 01089 ~21.92 miles southeast of Chesterfield
  • Includes a pool
  • 3 star hotel
From$74
Average 3.0 /5 Review Score Call BookMore Details
La Quinta by Wyndham in Springfield
+1-888-749-6785
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.
  • 3 star Downtown property
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
190 Meadow St., South Lee, MA 01260 ~23.58 miles west of Chesterfield
  • Pool in hotel: Two outdoor pools (seasonal) Two indoor pools (hours vary) Hot Tub (hours vary)
  • 3-star Mountain hotel
From$89
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Sheraton Springfield : 1 Monarch Place
+1-888-389-4485
1 Monarch Place, Springfield, MA 01144 ~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
  • 3-star Downtown hotel
From$80
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn Express Springfield Downtown
+1-888-389-4121
145 State St., Springfield, MA 01103 ~23.87 miles southeast of Chesterfield
  • Has swimming pool: Indoor heated pool
  • 3 star hotel
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Ludlow by IHG - Ludlow
+1-888-675-2083
321 Center St., Ludlow, MA 01056 ~24.05 miles southeast of Chesterfield
  • Has swimming pool: Heated indoor pool open 7am - 9pm daily.
  • 3 star Highway property
From$89
Very good 4.0 /5 Reviews Call BookMore Details
Vacation Village in The Berkshires - Lanesborough
+1-800-716-8490
276 Brodie Mtn Rd., Lanesborough, MA 01237 ~24.55 miles west of Chesterfield
  • Pool details: Pool hours 8am - 11pm Vacation Village in the Berkshires has a heated indoor swimming pool inside the clubhouse and a heated outdoor swimming pool located behind the clubhouse. Weather permitting, the outdoor pool is open seasonally from Memorial Day through Labor Day. Poolside lounge chairs are available to our owners and guests on a first-come, first-served basis. Pool towels are provided at each pool.
  • Midscale Mountain hotel
From$75
Very good 4.0 /5 Guest Reviews Call BookMore Details
Hotel Downstreet Ascend Hotel Collection - North Adams
+1-800-805-5223
40 Main St., North Adams, MA 01247 ~25.37 miles northwest of Chesterfield
  • Includes a pool: 5am-10pm Indoor
  • Midscale Downtown property
From$136
Very good 4.0 /5 Review Score Call BookMore Details
The Porches Inn at Mass Moca
+1-888-965-1860
231 River St., North Adams, MA 01247 ~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.
  • 4-star Downtown property
From$199
Very good 4.0 /5 Recent Reviews Call BookMore Details
Jiminy Peak Mountain Resort
+1-888-788-5576
37 Corey Rd., Hancock, MA 01237 ~25.75 miles west of Chesterfield
  • Pool in hotel: Country Inn Pool is open 8a - 10p daily. Outdoor heated pool open year round.
  • Three Star Mountain hotel
From$105
Very good 4.0 /5 Latest Reviews Call BookMore Details
Maple Terrace Motel
+1-888-897-9207
555 Main St., Williamstown, MA 01267 ~28.26 miles northwest of Chesterfield
  • Has swimming pool: Beautiful secluded heated pool with amazing and breathtaking views. Opens Daily 9 AM and closes at Dusk.
  • Economical Rural hotel
From$59
Very good 4.0 /5 Read Reviews Call BookMore Details
The Williams Inn in Williamstown
+1-888-311-4278
101 Spring St., Williamstown, MA 01267 ~28.67 miles northwest of Chesterfield
  • Includes a pool: Indoor heated pool and hot tub.
  • High-end Suburban property
From$125
Average 3.0 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi : 249 Stockbridge Rd.
+1-888-469-4795
249 Stockbridge Rd., Great Barrington, MA 01230 ~28.81 miles west of Chesterfield
  • Has a pool!
  • Mid-scale Resort property
From$109
Very good 4.0 /5 Recent Reviews Call BookMore Details
Hilton Garden Inn : Hartford North / Bradley Intl Airport
+1-888-734-9421
Hartford North / Bradley Intl Airport, Babc2af01bf25d1094cea9b5604bcbb1, CT 06095 ~32.24 miles south of Chesterfield
  • Pool details: 5:00am- 10:00pm
  • Affordable Airport property
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
The White House Inn
+1-888-841-5292
178 Vt 9 East, Wilmington, VT 05363 ~32.59 miles north of Chesterfield
  • Pool details: Small, shallow indoor pool, open 24 hours a day
  • 4-star Mountain property
From$75
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express & Suites Bradley Airport by IHG - Windsor Locks
+1-888-455-5160
600 Spring St., Windsor Locks, CT 06096 ~32.83 miles south of Chesterfield
  • Pool available: Indoor Heated Pool open from 7am - 8pm daily. approximately 12 feet x 15 feet.
  • Affordable Airport property
From$85
Very good 4.0 /5 Reviews Call BookMore Details
Springhill Suites Marriott Airport
+1-888-965-8297
225 Ella Grasso Turnpike, Windsor Locks, CT 06096 ~32.98 miles south of Chesterfield
  • Pool available: Small indoor heated pool. Not big enough for large groups of people.
  • Midscale Airport hotel
From$95
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Econo Lodge Inn & Suites Windsor Locks Bradley Airport - Windsor Locks
+1-888-906-6358
34 Old County Rd., Windsor Locks, CT 06096 ~33.28 miles south of Chesterfield
  • Pool in hotel: Seasonal-Outdoor
  • Low-priced Airport hotel
From$45
Average 3.0 /5 Latest Reviews Call BookMore Details
Econo Lodge Brattleboro : 515 Canal St.
+1-888-749-6785
515 Canal St., Brattleboro, VT 05301 ~33.78 miles northeast of Chesterfield
  • Has swimming pool
  • Low-priced Downtown property
From$53
Terrible 1.0 /5 Reviews Call BookMore Details
Courtyard By Marriott Hartford/Windsor Airport
+1-888-878-9982
1 Day Hill Rd., Windsor, CT 06095 ~34.17 miles south of Chesterfield
  • Has a pool!
  • 3 star Downtown hotel
From$219
Very good 4.0 /5 Recent Reviews Call BookMore Details
Baymont by Wyndham East Windsor Bradley Airport
+1-888-389-4485
260 Main St., East Windsor, CT 06088 ~34.74 miles south of Chesterfield
  • Includes a pool: Indoor Pool/ open from 5:30AM-11:00PM
  • 3 star Suburban hotel
From$40
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Express & Suites Brattleboro : 100 Chickering Dr.
+1-888-389-4121
100 Chickering Dr., Brattleboro, VT 05301 ~36.41 miles northeast of Chesterfield
  • Has swimming pool: Indoor pool/ open 5am-11pm
  • Mid-scale Suburban property
From$79
Very good 4.0 /5 Review Score Call BookMore Details
Colonial Motel And Spa : 889 Putney Rd.
+1-888-675-2083
889 Putney Rd., Brattleboro, VT 05301 ~36.48 miles northeast of Chesterfield
  • Pool details: 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
  • Mid-scale Rural hotel
From$59
Average 3.0 /5 Recent Reviews Call BookMore Details
Marriott Hartford/Windsor Airport : 28 Day Hill Rd.
+1-800-716-8490
28 Day Hill Rd., Windsor, CT 06095 ~36.82 miles south of Chesterfield
  • Pool in hotel: Inside pool open 7am - 11pm 24 Hour Fitness Center
  • Affordable Suburban hotel
From$90
Very good 4.0 /5 Review Score Call BookMore Details
Hyatt House Hartford North / Windsor : 200 Corporate Dr.
+1-800-805-5223
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
  • Mid-scale Suburban hotel
From$89
Average 3.0 /5 Review Score Call BookMore Details
Comfort Inn & Suites Brattleboro I 91
+1-888-965-1860
1186 Putney Rd., Brattleboro, VT 05301 ~37.09 miles northeast of Chesterfield
  • Pool in hotel: open 6am-10pm indoor heated pool. 3 foot deep to 5 foot deep
  • Cheap Highway property
From$79
Very good 4.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Brattleboro
+1-888-788-5576
1378 Putney Rd., Brattleboro, VT 05301 ~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'
  • Affordable Rural property
From$105
Very good 4.0 /5 Recent Reviews Call BookMore Details
Residence Inn by Marriott Hartford Windsor : 100 Dunfey Lane
+1-888-897-9207
100 Dunfey Lane, Windsor, CT 06095 ~38.03 miles south of Chesterfield
  • Pool details: Outdoor pool only open Memorial Day - Labor Day 10a-10p daily.
  • 3 star Highway property
From$96
Average 3.0 /5 Hotel Reviews Call BookMore Details
Mountaineer Inn
+1-888-311-4278
270 Handle Rd., Dover, VT 05356 ~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.
  • Inexpensive Mountain hotel
From$50
Average 3.0 /5 Reviews Call BookMore Details
Best Western Bennington : 220 Northside Dr.
+1-888-469-4795
220 Northside Dr., Bennington, VT 05201 ~39.82 miles northwest of Chesterfield
  • Pool in hotel: Outdoor, seasonal
  • Inexpensive Suburban hotel
From$36
Very good 4.0 /5 Review Score Call BookMore Details
Residence Inn by Marriott Hartford Avon - Avon
+1-888-734-9421
55 Simsbury Rd., Avon, CT 06001 ~39.88 miles south of Chesterfield
  • Includes a pool: Seasonal outdoor swimming pool and hot tub. Hours 9:00 AM - 9:00 PM.
  • 3 star Suburban property
From$80
Very good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn Bennington - Bennington
+1-888-841-5292
51 Hannaford Sq., Bennington, VT 05201 ~40.57 miles northwest of Chesterfield
  • Includes a pool: Indoor Pool is open from 7AM-10PM daily. Pool is 12,000 gallons
  • Three Star Mountain property
From$80
Average 3.0 /5 Reviews Call BookMore Details
Newly Remodeled Residence Inn by Marriott Hartford Manchester
+1-888-455-5160
201 Hale Rd., Manchester, CT 06042 ~43.07 miles southeast of Chesterfield
  • Includes a pool: Seasonal heated outdoor pool and hot tub
  • Mid-scale Suburban property
From$109
Very good 4.0 /5 Reviews Call BookMore Details
Homewood Suites by Hilton Hartford Manchester in Manchester
+1-888-965-8297
109 Pavilions Dr., Manchester, CT 06042 ~43.17 miles south of Chesterfield
  • Includes a pool: Indoor Heated Pool and Whirlpool Tub
  • Three Star Suburban property
From$99
Very good 4.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Sturbridge
+1-888-906-6358
328 Main St., Sturbridge, MA 01566 ~43.25 miles east of Chesterfield
  • We have a pool
  • Mid-scale Highway hotel
From$119
Very good 4.0 /5 Recent Reviews Call BookMore Details
Publick House Historic Inn and Country Motor Lodge : 277 Main St. (Rt 131)
+1-888-749-6785
277 Main St. (Rt 131), Sturbridge, MA 01566 ~43.53 miles east of Chesterfield
  • Includes a pool: Outdoor Pool
  • Inexpensive Rural property
From$61
Very good 4.0 /5 Latest Reviews Call BookMore Details
Interlaken Inn
+1-888-878-9982
74 Interlaken Rd., Lakeville, CT 06039 ~43.67 miles southwest of Chesterfield
  • Includes a pool: Seasonal Outdoor Heated Pool Open Memorial Day thru Labor Day
  • Affordable Resort property
From$179
Very good 4.0 /5 Latest Reviews Call BookMore Details

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