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.

Star Rating
Hotel Name
Price Range (USD) to
Amenities
+ More

Chesterfield Hotels with Outdoor or Indoor Pools

Fairfield Inn & Suites Springfield Northampton / Amherst : 115a Conz St. 115a Conz St., Northampton, MA 01060
Call Us
~12.19 miles east of Chesterfield
  • Pool in hotel
  • Three Star property
More Photos Photo of Fairfield Inn & Suites Springfield Northampton / Amherst Pool
From$118 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Tired of clicking around? Talk to an expert Hotel Planner: (855) 276-7561 or say...
alexa hotel planner skill"Alexa, ask Hotel Planner to make a new reservation in Chesterfield" Get Alexa Skill →
Quality Inn & Suites Northampton Amherst 117 Conz St., Northampton, MA 01060
Call Us
~12.26 miles east of Chesterfield
  • Pool in hotel: open from 6am - 10pm Heated indoor pool 5 1/3 in depth
  • Economical Highway property
More Photos Swimming pool at Quality Inn & Suites Northampton Amherst
From$102 total
Average 3.0 /5 Review Score Call BookMore Details
Hampton Inn Hadley Amherst Area - Hadley 24 Bay Rd., Hadley, MA 01035
Call Us
~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.
  • Three Star Suburban hotel
More Photos Swimming pool at Hampton Inn Hadley Amherst Area
From$130 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Towneplace Suites by Marriott : 237 Russell St. 237 Russell St., Hadley, MA 01035
Call Us
~14.02 miles east of Chesterfield
  • Pool available: Heated Indoor Pool open from 7am - 9pm daily.
  • Affordable Suburban property
More Photos Swimming pool at Towneplace Suites by Marriott
From$168 total
Average 3.0 /5 Read Reviews Call BookMore Details
Comfort Inn & Suites Hadley Amherst - Hadley 400 Russell St., Hadley, MA 01035
Call Us
~15.18 miles east of Chesterfield
  • Pool in hotel
  • Midscale Downtown property
More Photos Pool image of Comfort Inn & Suites Hadley Amherst
From$106 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Courtyard by Marriott Hadley Amherst in Hadley 423 Russell St., Hadley, MA 01035
Call Us
~15.43 miles east of Chesterfield
  • Includes a pool: 6AM-11PM Indoor Pool & Spa
  • Mid-scale Downtown property
More Photos Pool image of Courtyard by Marriott Hadley Amherst
From$130 total
Very Good 4.0 /5 Review Score Call BookMore Details
Fairfield Inn & Suites Springfield Holyoke in Holyoke 229 Whiting Farms Rd., Holyoke, MA 01040
Call Us
~18.05 miles southeast of Chesterfield
  • Includes a pool: Indoor and heated pool open from 6AM to 10PM
  • 3 star Suburban property
More Photos Photo of Fairfield Inn & Suites Springfield Holyoke Pool
From$130 total
Very Good 4.0 /5 Review Score Call BookMore Details
Hampton Inn Chicopee / Springfield 600 Memorial Dr., Chicopee, MA 01020
Call Us
~20.13 miles southeast of Chesterfield
  • Pool available: Relax in our Indoor Pool open 9 AM - 10 PM.
  • 3 star Suburban hotel
More Photos Photo of Hampton Inn Chicopee / Springfield Pool
From$130 total
Very Good 4.0 /5 Review Score Call BookMore Details
Residence Inn by Marriott Springfield Chicopee : 500 Memorial Dr. 500 Memorial Dr., Chicopee, MA 01020
Call Us
~20.25 miles southeast of Chesterfield
  • Pool available: Indoor pool Pool Hours 9am to 10pm
  • Three Star Highway property
More Photos Swimming pool at Residence Inn by Marriott Springfield Chicopee
From$118 total
Very Good 4.0 /5 Reviews Call BookMore Details
TRU by Hilton Chicopee Springfield : 440 Memorial Dr. 440 Memorial Dr., Chicopee, MA 01020
Call Us
~20.28 miles southeast of Chesterfield
  • Includes a pool: Indoor Pool. Open 7AM-10PM daily.
  • Affordable hotel
More Photos Photo of TRU by Hilton Chicopee Springfield Pool
From$118 total
Average 3.0 /5 Reviews Call BookMore Details
Residence Inn by Marriott West Springfield : 64 Border Way 64 Border Way, West Springfield, MA 01089
Call Us
~20.55 miles southeast of Chesterfield
  • Pool in hotel: Indoor pool open from 6am-12am daily
  • Three Star Highway hotel
More Photos Swimming pool at Residence Inn by Marriott West Springfield
From$116 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Comfort Inn & Suites : 106 Capital Dr. 106 Capital Dr., West Springfield, MA 01089
Call Us
~20.81 miles southeast of Chesterfield
  • Pool available: Indoor pool and whirlpool open daily from 7am-10pm
  • Inexpensive Suburban property
More Photos Photo of Comfort Inn & Suites Pool
From$154 total
Average 3.0 /5 Latest Reviews Call BookMore Details
Quality Inn West Springfield in West Springfield 1150 Riverdale St., West Springfield, MA 01089
Call Us
~20.86 miles southeast of Chesterfield
  • Pool details: Covered seasonal outdoor pool Handicapped lift open 10am to 10pm
  • Low Cost Suburban hotel
More Photos Pool image of Quality Inn West Springfield
From$90 total
Average 3.0 /5 Guest Reviews Call BookMore Details
More Homes & Apts at Booking.com

Book online or call +1-800-219-2797

Booking for Homes and Apartments
Go to BookingGo to Booking
Courtyard West Spring Marriott 885 Riverdale St., West Springfield, MA 01089
Call Us
~21.27 miles southeast of Chesterfield
  • We have a pool ready for use
  • 3 star hotel
More Photos Photo of Courtyard West Spring Marriott Pool
From$108 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Pittsfield Lenox Berkshires - Pittsfield 1055 South St., Pittsfield, MA 01201
Call Us
~21.56 miles west of Chesterfield
  • Has swimming pool: Indoor heated pool & hot tub, hours: 8am - 10pm, Deep end: 5 feet
  • Affordable Suburban hotel
More Photos Photo of Holiday Inn Express Pittsfield Lenox Berkshires Pool
From$96 total
Average 3.0 /5 Latest Reviews Call BookMore Details
Need some questions answered? Talk to an expert Hotel Planner: (855) 276-7561 or say...
alexa hotel planner skill"Alexa, ask Hotel Planner to make a new reservation in Chesterfield" Get Alexa Skill →
Berkshire Mountain Lodge in Pittsfield 8 Dan Fox Dr., Pittsfield, MA 01201
Call Us
~21.64 miles west of Chesterfield
  • Has swimming pool: Indoor pool & hot tub Open daily 8am-11pm
  • Cheap Mountain property
More Photos Swimming pool at Berkshire Mountain Lodge
From$150 total
Very Good 4.5 /5 Review Score Call BookMore Details
Hilton Garden Inn Lenox Pittsfield in Pittsfield 1032 South St., Pittsfield, MA 01201
Call Us
~21.71 miles west of Chesterfield
  • Pool in hotel: Indoor heated pool/hot tub
  • Midscale Suburban hotel
More Photos Pool image of Hilton Garden Inn Lenox Pittsfield
From$114 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Hampton Inn & Suites Lenox Berkshires : 445 Pittsfield Rd. 445 Pittsfield Rd., Lenox, MA 01240
Call Us
~21.84 miles west of Chesterfield
  • Our hotel comes with a pool
  • Mid-scale Mountain hotel
More Photos Swimming pool at Hampton Inn & Suites Lenox Berkshires
From$96 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Best Western Springfield West Inn 429 Riverdale St., West Springfield, MA 01089
Call Us
~21.92 miles southeast of Chesterfield
  • Pool in hotel
  • Affordable hotel
More Photos Photo of Best Western Springfield West Inn Pool
From$87 total
Average 3.0 /5 Reviews Call BookMore Details
La Quinta by Wyndham : 100 Congress St. 100 Congress St., Springfield, MA 01104
Call Us
~23.19 miles southeast of Chesterfield
  • Includes a 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
More Photos Pool image of La Quinta by Wyndham
From$96 total
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort - South Lee 190 Meadow St., South Lee, MA 01260
Call Us
~23.58 miles west of Chesterfield
  • Pool available: Two outdoor pools (seasonal) Two indoor pools (hours vary) Hot Tub (hours vary)
  • 3-star Mountain hotel
More Photos Swimming pool at Holiday Inn Club Vacations Oak N Spruce Resort
From$106 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Sheraton Springfield Monarch Place Hotel in Springfield 1 Monarch Place, Springfield, MA 01144
Call Us
~23.72 miles southeast of Chesterfield
  • Pool available: 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 property
More Photos Swimming pool at Sheraton Springfield Monarch Place Hotel
From$96 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Springfield Downtown 145 State St., Springfield, MA 01103
Call Us
~23.87 miles southeast of Chesterfield
  • Pool available: Indoor heated pool
  • Affordable hotel
More Photos hotel room
From$96 total
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn & Suites Springfield/Downtown in Springfield 851 East Columbus Ave., Springfield, MA 01105
Call Us
~24.46 miles southeast of Chesterfield
  • Includes a pool: 7am-10Pm
  • Affordable Downtown property
More Photos Swimming pool at Hampton Inn & Suites Springfield/Downtown
From$118 total
Very Good 4.0 /5 Review Score Call BookMore Details
Vacation Village in The Berkshires in Lanesborough 276 Brodie Mtn Rd., Lanesborough, MA 01237
Call Us
~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.
  • Mid-scale Mountain hotel
More Photos Photo of Vacation Village in The Berkshires Pool
From$90 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
The Red Lion Inn 30 Main St., Stockbridge, MA 01262
Call Us
~25.25 miles west of Chesterfield
  • Pool available: 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!
  • Mid-scale Rural property
More Photos Pool image of The Red Lion Inn
From$144 total
Average 3.0 /5 Reviews Call BookMore Details
The Porches Inn at Mass Moca in North Adams 231 River St., North Adams, MA 01247
Call Us
~25.56 miles northwest of Chesterfield
  • Has swimming pool: Outdoor heated pool open 24 hours daily year round. Sauna, outdoor hot tub and 24 hour fitness Center onsite.
  • Four-star Downtown hotel
More Photos Photo of The Porches Inn at Mass Moca Pool
From$238 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Jiminy Peak Mountain Resort in Hancock 37 Corey Rd., Hancock, MA 01237
Call Us
~25.75 miles west of Chesterfield
  • Pool available: Country Inn Pool is open 8a - 10p daily. Outdoor heated pool open year round.
  • Three Star Mountain property
More Photos Swimming pool at Jiminy Peak Mountain Resort
From$126 total
Very Good 4.0 /5 Review Score Call BookMore Details
The Orchards Hotel : 222 Adams Rd. 222 Adams Rd., Williamstown, MA 01267
Call Us
~28.06 miles northwest of Chesterfield
  • Has a pool!
  • Four star Suburban hotel
More Photos Swimming pool at The Orchards Hotel
From$130 total
Average 3.0 /5 Review Score Call BookMore Details
Maple Terrace Motel 555 Main St., Williamstown, MA 01267
Call Us
~28.26 miles northwest of Chesterfield
  • Pool in hotel: Beautiful secluded heated pool with amazing and breathtaking views. Opens Daily 9 AM and closes at Dusk.
  • 2 star Rural property
More Photos Pool image of Maple Terrace Motel
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
Call Us
~28.78 miles southeast of Chesterfield
  • Pool details: Seasonal Outdoor Pool- 9am-9pm
  • Affordable Suburban hotel
More Photos Swimming pool at Fairfield Inn & Suites by Marriott Springfield Enfield
From$94 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox / Berks : 249 Stockbridge Rd. 249 Stockbridge Rd., Great Barrington, MA 01230
Call Us
~28.81 miles west of Chesterfield
  • We have a pool
  • Midscale Resort property
More Photos Photo of Fairfield Inn & Suites by Marriott Great Barrington Lenox / Berks Pool
From$130 total
Very Good 4.0 /5 Read Reviews Call BookMore Details
The Williams Inn in Williamstown 1090 Main St., Williamstown, MA 01267
Call Us
~29.07 miles northwest of Chesterfield
  • Includes a pool: Indoor heated pool and hot tub.
  • 4 star Suburban hotel
More Photos Pool image of The Williams Inn
From$114 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hilton Garden Inn - Babc2af01bf25d1094cea9b5604bcbb1 Hartford North / Bradley Intl Airport, Babc2af01bf25d1094cea9b5604bcbb1, CT 06095
Call Us
~32.24 miles south of Chesterfield
  • Pool in hotel: 5:00am- 10:00pm
  • 3 star Airport hotel
More Photos Photo of Hilton Garden Inn Pool
From$96 total
Average 3.0 /5 Read Reviews Call BookMore Details
The White House Inn : 178 Vt 9 East 178 Vt 9 East, Wilmington, VT 05363
Call Us
~32.59 miles north of Chesterfield
  • Pool available: Small, shallow indoor pool, open 24 hours a day
  • High-end Mountain hotel
More Photos Photo of The White House Inn Pool
From$90 total
Average 3.0 /5 Reviews Call BookMore Details
Springhill Suites Marriott Airport - Windsor Locks 225 Ella Grasso Turnpike, Windsor Locks, CT 06096
Call Us
~32.98 miles south of Chesterfield
  • Has swimming pool: Small indoor heated pool. Not big enough for large groups of people.
  • 3 star Airport hotel
More Photos Swimming pool at Springhill Suites Marriott Airport
From$114 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Econo Lodge Inn & Suites Windsor Locks Bradley Airport : 34 Old County Rd. 34 Old County Rd., Windsor Locks, CT 06096
Call Us
~33.28 miles south of Chesterfield
  • Pool in hotel: 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 - Windsor Locks 2 Loten Dr., Windsor Locks, CT 06096
Call Us
~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 by Marriott Hartford Airport Pool
From$114 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Homewood Suites by Hilton Windsor Locks Hartford 65 Ella Grasso Turnpike, Windsor Locks, CT 06096
Call Us
~33.76 miles south of Chesterfield
  • Has swimming pool: We offer an outside swimming pool that is open from Memorial Day weekend through Labor Day weekend. Hours of operation daily: 10am-9pm.
  • Midscale Airport hotel
More Photos Photo of Homewood Suites by Hilton Windsor Locks Hartford Pool
From$118 total
Very Good 4.0 /5 Reviews Call BookMore Details
Econo Lodge Brattleboro South - Brattleboro 515 Canal St., Brattleboro, VT 05301
Call Us
~33.78 miles northeast of Chesterfield
  • Has a pool!
  • Low-priced Downtown property
More Photos Pool image of Econo Lodge Brattleboro South
From$63 total
Not Good 1.0 /5 Hotel 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
Call Us
~33.79 miles south of Chesterfield
  • Pool available: The hotel offers an indoor heated pool. It is open from 7am-10pm daily
  • 3 star Airport property
More Photos Pool image of Doubletree by Hilton Hotel Hartford Bradley Airport
From$87 total
Average 3.5 /5 Read Reviews Call BookMore Details
Courtyard By Marriott Hartford/Windsor Airport in Windsor 1 Day Hill Rd., Windsor, CT 06095
Call Us
~34.17 miles south of Chesterfield
  • Pool in hotel
  • Midscale Downtown hotel
More Photos Pool image of Courtyard By Marriott Hartford/Windsor Airport
From$262 total
Very Good 4.0 /5 Review Score Call BookMore Details
Baymont by Wyndham East Windsor Bradley Airport 260 Main St., East Windsor, CT 06088
Call Us
~34.74 miles south of Chesterfield
  • Has swimming pool: Indoor Pool/ open from 5:30AM-11:00PM
  • Affordable Suburban hotel
More Photos Photo of Baymont by Wyndham East Windsor Bradley Airport Pool
From$48 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Ramada by Wyndham Windsor Locks - Windsor Locks 383 South Center St., Windsor Locks, CT 06096
Call Us
~35.20 miles south of Chesterfield
  • Includes a 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 Latest Reviews Call BookMore Details
Holiday Inn Express & Suites Brattleboro 100 Chickering Dr., Brattleboro, VT 05301
Call Us
~36.41 miles northeast of Chesterfield
  • Has swimming pool: Indoor pool/ open 5am-11pm
  • 3-star Suburban hotel
More Photos Pool image of Holiday Inn Express & Suites Brattleboro
From$94 total
Very Good 4.0 /5 Reviews Call BookMore Details
Black Mountain Inn 959 Putney Rd., Brattleboro, VT 05301
Call Us
~36.60 miles northeast of Chesterfield
  • Includes a pool: Seasonal outdoor pool
  • Economical Suburban hotel
More Photos Pool image of Black Mountain Inn
From$68 total
Average 3.5 /5 Review Score Call BookMore Details
Hyatt House Hartford North / Windsor in Windsor 200 Corporate Dr., Windsor, CT 06095
Call Us
~37.07 miles south of Chesterfield
  • Pool details: Indoor heated pool and whirlpool 6 am - 9 pm *Limit four (4) guests per room
  • Mid-scale Suburban property
More Photos Swimming pool at Hyatt House Hartford North / Windsor
From$106 total
Average 3.0 /5 Read Reviews Call BookMore Details
Comfort Inn & Suites Brattleboro I 91 in Brattleboro 1186 Putney Rd., Brattleboro, VT 05301
Call Us
~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 hotel
More Photos Pool image of Comfort Inn & Suites Brattleboro I 91
From$94 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn Brattleboro in Brattleboro 1378 Putney Rd., Brattleboro, VT 05301
Call Us
~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'
  • 3 star Rural hotel
More Photos Pool image of Hampton Inn Brattleboro
From$126 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Residence Inn by Marriott Hartford Windsor in Windsor 100 Dunfey Lane, Windsor, CT 06095
Call Us
~38.03 miles south of Chesterfield
  • Pool in hotel: Outdoor pool only open Memorial Day - Labor Day 9a-9p daily.
  • Mid-scale Highway property
More Photos Swimming pool at Residence Inn by Marriott Hartford Windsor
From$115 total
Average 3.0 /5 Latest Reviews Call BookMore Details

Next: Show All Available Chesterfield Hotels with Pricing
Back to Top