Winchester Hotels with Pools - Outdoor/Indoor Pools in Winchester MA

Winchester 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 Winchester, MA for your upcoming individual or family vacation. We list the best pool equipped, kid friendly Winchester Massachusetts hotel and motel rooms for children. Review the list of Winchester hotels with indoor or outdoor pools below to find the perfect lodging for you and your kids.
Planning group travel? Get Winchester MA Group Hotel Rates

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

Winchester Hotels with Outdoor or Indoor Pools

Hampton Inn & Homewood Suites by Hilton Boston Woburn : 371 Washington St. 371 Washington St., Woburn, MA 01801
Call Us
~0.63 miles northeast of Winchester
  • Pool available: Indoor Salt-Water Infused Pool
  • Affordable Suburban property
More Photos Photo of Hampton Inn & Homewood Suites by Hilton Boston Woburn Pool
From$80
Average 3.0 /5 Review Score 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 Winchester" Get Alexa Skill →
Best Western Plus New Englander : 1 Rainin Rd. 1 Rainin Rd., Woburn, MA 01801
Call Us
~1.99 miles northeast of Winchester
  • Has swimming pool: Indoor heated pool Open 6 am - 10 pm
  • 3 star Suburban hotel
More Photos Photo of Best Western Plus New Englander Pool
From$72
Average 3.5 /5 Hotel Reviews Call BookMore Details
Hilton Boston / Woburn - Woburn 2 Forbes Rd., Woburn, MA 01801
Call Us
~2.86 miles north of Winchester
  • Pool details: Indoor
  • Mid-scale Suburban property
More Photos Pool image of Hilton Boston / Woburn
From$79
Very Good 4.0 /5 Reviews Call BookMore Details
Crowne Plaza Boston - Woburn by IHG : 15 Middlesex Canal Park 15 Middlesex Canal Park, Woburn, MA 01801
Call Us
~2.99 miles north of Winchester
  • Pool details: Open from 7am to 10pm. Reservations Required.
  • High-end Suburban property
More Photos Photo of Crowne Plaza Boston - Woburn by IHG Pool
From$105
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn Woburn Boston in Woburn 371a Washington St., Woburn, MA 01801
Call Us
~3.00 miles north of Winchester
  • Pool available: Indoor Salt-Water Infused Pool
  • 3 star Suburban hotel
More Photos Pool image of Hampton Inn Woburn Boston
From$129
Average 3.0 /5 Read Reviews Call BookMore Details
Hyatt Place Boston/Medford : 116 Riverside Ave. 116 Riverside Ave., Medford, MA 02155
Call Us
~3.11 miles southeast of Winchester
  • Pool in hotel: Our indoor pool is open between the hours of 6:00AM and 10:00PM.
  • 3-star Suburban hotel
More Photos Swimming pool at Hyatt Place Boston/Medford
From$89
Very Good 4.0 /5 Review Score Call BookMore Details
Fairfield Inn Boston Woburn / Burlington 285 Mishawum Rd., Woburn, MA 01801
Call Us
~3.32 miles north of Winchester
  • Pool available: Seasonal outdoor pool
  • Affordable Highway property
More Photos Photo of Fairfield Inn Boston Woburn / Burlington Pool
From$64
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Hyatt House Boston Burlington : 2 Van De Graaff Dr. 2 Van De Graaff Dr., Burlington, MA 01803
Call Us
~3.50 miles northwest of Winchester
  • Pool available: The hotel pool is open seasonally from Memorial Day to Labor Day. It is open from 10am-10pm weather dependent during that time.
  • Mid-scale Suburban property
More Photos Photo of Hyatt House Boston Burlington Pool
From$42
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Boston Marriott Burlington 1 Burlington Mall Rd., Burlington, MA 01803
Call Us
~3.89 miles northwest of Winchester
  • Has swimming pool: Indoor Pool 6AM - 11PM Outdoor Pool 6AM - Dusk
  • Expensive Suburban hotel
More Photos Photo of Boston Marriott Burlington Pool
From$119
Very Good 4.0 /5 Recent Reviews Call BookMore Details
AC Hotel Boston Cambridge 10 Acorn Park Dr., Cambridge, MA 02140 Website
Call Us
~3.93 miles south of Winchester
  • Includes a pool: Indoor heated salt water pool open from 7am to 10pm.
  • Affordable Suburban property
More Photos Swimming pool at AC Hotel Boston Cambridge
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Residence Inn by Marriott Boston Woburn in Woburn 300 Presidential Way, Woburn, MA 01801
Call Us
~4.50 miles north of Winchester
  • Has swimming pool: Heated indoor pool and whirlpool. Open 7 days a week from 6:00AM-10:00PM
  • Three Star Suburban property
More Photos Swimming pool at Residence Inn by Marriott Boston Woburn
From$110
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Boston Cambridge Area 30 Washington St., Somerville, MA 02143
Call Us
~5.83 miles southeast of Winchester
  • Includes a pool: * POOL/ FITNESS CENTER Dive-In Movies on Friday and Saturday nights. The hotel pool features a basketball sport court, foosball, table tennis, bumper pool, 12 ft rock climbing wall and a 16 ft projection TV for movies/sports. Enjoy one of our relaxing cabana areas while the kids have fun.Indoor Pool Heated Indoor Pool Indoor Pool Hours of Operation: varies Dive-In Movies on Friday and Saturday nights. The hotel pool features a basketball sport court, foosball, bumper pool, 12 ft rock climbing wall and a 16 ft projection TV for movies/sports. Enjoy one of our relaxing cabana areas while the kids have fun. Complimentary Fitness Center Hours of Operation: 24 hours with guest key card Free weights, Hammer Strength equipment, and cardio equipment (including LifeCycle, elliptical trainers and treadmills).
  • Mid-scale Downtown hotel
More Photos Photo of Holiday Inn Boston Cambridge Area Pool
From$80
Average 3.0 /5 Review Score Call BookMore Details
Element Lexington 727 B Marrett Rd., Lexington, MA 02421
Call Us
~6.29 miles west of Winchester
  • Pool in hotel: Whether you start your day with laps or take a dip to unwind at the end of the day, the indoor salt water swimming pool at Element Lexington is an invigorating space, morning through night. It’s open to our guests of all ages every day of the year, 6am to 11pm.
  • Three Star Suburban hotel
More Photos Photo of Element Lexington Pool
From$80
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
Aloft Lexington : 727 a Marrett Rd. 727 a Marrett Rd., Lexington, MA 02421
Call Us
~6.29 miles west of Winchester
  • Pool details: Wind down after a workout or just take a quiet timeout to yourself at splash, Aloft Lexington’s refreshing indoor salt water pool. It’s great for a leisurely swim—or even some poolside email catch-up, thanks to free wireless Internet service. And it's even eco-friendly, using a cleaner, greener saline solution! Early birds and night owls equally welcome, with hours from 6am to 11pm
  • Midscale Suburban property
More Photos Swimming pool at Aloft Lexington
From$76
Very Good 4.0 /5 Reviews Call BookMore Details
Homewood Suites by Hilton Boston Billerica / Bedford / Burlington in Billerica 35 Middlesex Turnpike, Billerica, MA 01821
Call Us
~6.30 miles northwest of Winchester
  • We have a pool ready for use
  • Affordable Suburban hotel
More Photos Swimming pool at Homewood Suites by Hilton Boston Billerica / Bedford / Burlington
From$80
Average 3.0 /5 Hotel 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 Winchester" Get Alexa Skill →
Homewood Suites Boston Logan Airport Chelsea - Chelsea 145 Beech St., Chelsea, MA 02150
Call Us
~6.36 miles southeast of Winchester
  • Includes a pool: Indoor Heated Salt Water Pool- 7am to 10pm
  • Three Star Airport property
More Photos Swimming pool at Homewood Suites Boston Logan Airport Chelsea
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Residence Inn Boston Logan Airport/Chelsea in Chelsea 200 a Maple St., Chelsea, MA 02150
Call Us
~6.40 miles southeast of Winchester
  • Pool available: Our Indoor heated saltwater pool is open from 10am to 10pm
  • Midscale Downtown property
More Photos Swimming pool at Residence Inn Boston Logan Airport/Chelsea
From$129
Average 3.0 /5 Reviews Call BookMore Details
Residence Inn Boston Watertown - Watertown 570 Arsenal St., Watertown, MA 02472
Call Us
~6.44 miles south of Winchester
  • Pool available: Indoor, heated pool is open daily from 8AM - 11PM.
  • Midscale Suburban property
More Photos Swimming pool at Residence Inn Boston Watertown
From$129
Average 3.0 /5 Recent Reviews Call BookMore Details
Four Points by Sheraton Boston Logan Airport Revere - Revere 407 Squire Rd., Revere, MA 02151
Call Us
~6.47 miles east of Winchester
  • Pool details: 6am - 10pm, indoor heated pool
  • 3-star Airport property
More Photos Swimming pool at Four Points by Sheraton Boston Logan Airport Revere
From$149
Average 3.0 /5 Guest Reviews Call BookMore Details
The Royal Sonesta Boston - Cambridge 40 Edwin Land Blvd., Cambridge, MA 02142
Call Us
~6.88 miles southeast of Winchester
  • Pool available: Open 6AM - 10PM. Our atrium-style lap pool, measuring 30' x 45', is one of the largest pools in the Boston and Cambridge area. We are proud to offer a chlorine-free, salt-based pool which is gentler to the skin and eyes. With lap lanes and an area for less strenuous pursuits, the pool is perfect for taking a dip or getting in a workout. Please note: the pool does not have a lifeguard on duty. Children 16 and under need to be accompanied by an adult.
  • 4-star Downtown property
More Photos Swimming pool at The Royal Sonesta Boston
From$100
Very Good 4.0 /5 Review Score Call BookMore Details
Residence Inn by Marriott Boston Harbor on Tudor Wharf 34 44 Charles River Ave., Boston, MA 02129
Call Us
~7.06 miles southeast of Winchester
  • Includes a pool: Take a splash in our indoor heated pool overlooking Boston Harbor. Open daily from 6am - 10pm and complimentary for all hotel guests.
  • Midscale Oceanfront hotel
More Photos Photo of Residence Inn by Marriott Boston Harbor on Tudor Wharf Pool
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Four Points by Sheraton Boston Newton : 320 Washington St. 320 Washington St., Newton, MA 02458
Call Us
~7.27 miles south of Winchester
  • Has swimming pool: While staying with us, unwind in our newly renovated indoor heated pool, located on the 3rd floor with expansive views overlooking the highway. Whether you're looking to start your day with a swim or relax after a busy schedule, the pool offers a refreshing retreat year-round. Open daily from 7:00 AM to 10:00 PM for hotel guests.
  • 3 star Suburban hotel
More Photos Photo of Four Points by Sheraton Boston Newton Pool
From$99
Average 3.5 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Boston/Waltham - Waltham 450 Totten Pond Rd., Waltham, MA 02451
Call Us
~7.30 miles southwest of Winchester
  • Includes a pool: Indoor pool open daily from 7am - 10pm.
  • Midscale Highway property
More Photos Pool image of Hilton Garden Inn Boston/Waltham
From$82
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Best Western Plus Waltham Boston 380 Winter St., Waltham, MA 02451
Call Us
~7.33 miles southwest of Winchester
  • We have a pool ready for use
  • Affordable property
More Photos Swimming pool at Best Western Plus Waltham Boston
From$85
Average 3.0 /5 Recent Reviews Call BookMore Details
Wyndham Boston Beacon Hill 5 Blossom St., Boston, MA 02114
Call Us
~7.39 miles southeast of Winchester
  • Pool in hotel: Seasonal outdoor pool, typically open Memorial Day to Labor Day.
  • High end Downtown hotel
More Photos Pool image of Wyndham Boston Beacon Hill
From$125
Average 3.0 /5 Hotel Reviews Call BookMore Details
HYATT house Boston/Waltham - Waltham 54 4th Ave., Waltham, MA 02451
Call Us
~7.42 miles southwest of Winchester
  • Pool available: Heated outdoor pool open Memorial Day through Labor Day.
  • Three Star Suburban hotel
More Photos Pool image of HYATT house Boston/Waltham
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
TownePlace Suites Boston Logan Airport/Chelsea : 30 Eastern Ave. 30 Eastern Ave., Chelsea, MA 02150
Call Us
~7.42 miles southeast of Winchester
  • Pool in hotel: Indoor Heated Saltwater Pool open from 7AM to 10PM.
  • 3-star Airport hotel
More Photos Swimming pool at TownePlace Suites Boston Logan Airport/Chelsea
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
The Westin Waltham Boston - Waltham 70 3rd Ave., Waltham, MA 02451
Call Us
~7.50 miles southwest of Winchester
  • Pool in hotel: Located on the lower level of the hotel, our indoor heated pool makes aquatic fun a year-round activity. Relax on a chaise lounge and enjoy views of the grounds from floor-to-ceiling windows. The pool is 350 sq ft. It is open from 6:00am-11pm
  • 4-star Suburban hotel
More Photos Photo of The Westin Waltham Boston Pool
From$109
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Boston - Logan Airport in Revere 230 Lee Burbank Highway, Revere, MA 02151
Call Us
~7.64 miles east of Winchester
  • Includes a pool: Indoor pool, open 8AM-8PM
  • 3-star Airport hotel
More Photos Pool image of Hampton Inn Boston - Logan Airport
From$84
Average 3.0 /5 Review Score Call BookMore Details
Embassy Suites by Hilton Boston Waltham in Waltham 550 Winter St., Waltham, MA 02451
Call Us
~7.73 miles southwest of Winchester
  • Pool in hotel: 7am to 9pm Daily 40 x 20 Indoor
  • 3-star Suburban hotel
More Photos Swimming pool at Embassy Suites by Hilton Boston Waltham
From$80
Average 3.0 /5 Reviews Call BookMore Details
The Arcadian Hotel 1200 Beacon St., Brookline, MA 02446
Call Us
~7.75 miles south of Winchester
  • Pool available: Heated indoor saltwater pool and hot tub, 9am-9pm
  • 3-star Downtown hotel
More Photos Photo of The Arcadian Hotel Pool
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Residence Inn by Marriott Back Bay / Fenway - Boston 125 Brookline Ave., Boston, MA 02215
Call Us
~7.78 miles south of Winchester
  • Pool details: Indoor pool located on our Rooftop Terrace Open from 7am - 9:30pm
  • 3 star Downtown property
More Photos Swimming pool at Residence Inn by Marriott Back Bay / Fenway
From$159
Very Good 4.0 /5 Review Score Call BookMore Details
Hampton Inn & Suites Boston / Waltham in Waltham 135 2nd Ave., Waltham, MA 02451
Call Us
~7.86 miles southwest of Winchester
  • Pool details: Indoor Heated Pool
  • 3-star Suburban property
More Photos Pool image of Hampton Inn & Suites Boston / Waltham
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Courtyard by Marriott Boston Brookline in Brookline 40 Webster St., Brookline, MA 02446
Call Us
~7.93 miles south of Winchester
  • Pool in hotel: 8am-10pm, indoor lap pool. Heated to utilize during the winter.
  • Affordable Downtown property
More Photos Swimming pool at Courtyard by Marriott Boston Brookline
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
The Langham Boston - Boston 250 Franklin St., Boston, MA 02110
Call Us
~8.03 miles southeast of Winchester
  • Includes a pool: Take a dip in the sparkling waters of our 40-foot heated indoor pool. Spend the day in our sunlit pavilion complete with a whirlpool or unwind in our peaceful saunas. 6:30am – 9pm, daily
  • Luxurious 5 Star Downtown property
More Photos Pool image of The Langham Boston
From$160
Very Good 4.0 /5 Read Reviews Call BookMore Details
Boston Harbor Hotel 70 Rowes Wharf, Boston, MA 02110
Call Us
~8.12 miles southeast of Winchester
  • Includes a pool: 60 ft. lap pool Monday - Friday 5:30am - 9:00pm Saturday 7:00am - 9:00pm Sunday 7:00am - 8:00pm pool and hot tub renovation till May 15, 2025.
  • Luxurious Five Star Downtown property
More Photos Swimming pool at Boston Harbor Hotel
From$325
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Homewood Suites by Hilton Boston Brookline-Longwood Medical 111 Boylston St., Brookline, MA 02445
Call Us
~8.61 miles south of Winchester
  • Pool in hotel: Our pool is currenlt closed due to the pandemic
  • Midscale Suburban property
More Photos Swimming pool at Homewood Suites by Hilton Boston Brookline-Longwood Medical
From$80
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Homewood Suites by Hilton Boston-Peabody in Peabody 57 Newbury St., Peabody, MA 01960
Call Us
~8.76 miles northeast of Winchester
  • Pool available: Indoor pool 8 am to 10 pm
  • 3-star Highway hotel
More Photos Swimming pool at Homewood Suites by Hilton Boston-Peabody
From$89
Very Good 4.0 /5 Read Reviews Call BookMore Details
Courtyard by Marriott Boston Billerica / Bedford 270 Concord Rd., Billerica, MA 01821
Call Us
~9.48 miles northwest of Winchester
  • Includes a pool: The pool is 15x35 and 4'6" deep at the mid point. Hours are 6am - 11pm
  • Midscale Suburban property
More Photos Swimming pool at Courtyard by Marriott Boston Billerica / Bedford
From$83
Average 3.5 /5 Latest Reviews Call BookMore Details
Boston Marriott Peabody - Peabody 8a Centennial Dr., Peabody, MA 01960
Call Us
~10.08 miles east of Winchester
  • With a pool!
  • 4 star Suburban hotel
More Photos Pool image of Boston Marriott Peabody
From$125
Average 3.0 /5 Review Score Call BookMore Details
Candlewood Suites Boston North Shore Danvers by IHG in Danvers 238 Andover St., Danvers, MA 01923
Call Us
~10.86 miles northeast of Winchester
  • Pool details: Outdoor pool open Memorial Day-Labor Day
  • Economy Suburban property
More Photos Photo of Candlewood Suites Boston North Shore Danvers by IHG Pool
From$109
Very Good 4.0 /5 Review Score Call BookMore Details
Best Western Plus North Shore Hotel : 50 Dayton St. 50 Dayton St., Danvers, MA 01923
Call Us
~11.41 miles northeast of Winchester
  • Has swimming pool: Indoor Heated Pool
  • Mid-scale Suburban property
More Photos Swimming pool at Best Western Plus North Shore Hotel
From$82
Very Good 4.0 /5 Reviews Call BookMore Details
Homewood Suites by Hilton Needham Boston - Needham 200 1st Ave., Needham, MA 02494
Call Us
~11.49 miles southwest of Winchester
  • Pool details: Indoor pool 7:00am - 10:00pm.
  • Mid-scale Suburban property
More Photos Pool image of Homewood Suites by Hilton Needham Boston
From$139
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Sonesta Select Boston Danvers 275 Independence Way, Danvers, MA 01923
Call Us
~12.26 miles northeast of Winchester
  • Pool details: Outdoor Pool - Summer Seasonal
  • Three Star Suburban hotel
More Photos Pool image of Sonesta Select Boston Danvers
From$80
Average 3.0 /5 Reviews Call BookMore Details
Doubletree by Hilton Boston North Shore - Danvers 50 Ferncroft Rd., Danvers, MA 01923
Call Us
~12.97 miles northeast of Winchester
  • Includes a pool: Hours of Operations from 6:00AM - 10:00PM.
  • 3 star Suburban property
More Photos Photo of Doubletree by Hilton Boston North Shore Pool
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Salem Waterfront Hotel & Suites : 225 Derby St. 225 Derby St., Salem, MA 01970
Call Us
~13.39 miles east of Winchester
  • Includes a swimming pool
  • High end Oceanfront property
More Photos Pool image of Salem Waterfront Hotel & Suites
From$269
Very Good 4.0 /5 Reviews Call BookMore Details
Sonesta Select Boston Lowell Chelmsford : 30 Industrial Ave. East 30 Industrial Ave. East, Lowell, MA 01852
Call Us
~14.36 miles northwest of Winchester
  • Pool in hotel: Currently not open
  • Mid-scale Suburban hotel
More Photos Photo of Sonesta Select Boston Lowell Chelmsford Pool
From$119
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Hampton Inn & Suites Westford-Chelmsford : 9 Nixon Rd. 9 Nixon Rd., Westford, MA 01886
Call Us
~16.44 miles northwest of Winchester
  • Pool in hotel: Indoor Pool- 6am to 10pm
  • 3 star Suburban hotel
More Photos Photo of Hampton Inn & Suites Westford-Chelmsford Pool
From$89
Very Good 4.0 /5 Reviews Call BookMore Details
Courtyard by Marriott Boston Dedham / Westwood in Westwood 64 University Ave., Westwood, MA 02090
Call Us
~16.86 miles south of Winchester
  • Pool in hotel: There is 2 indoor pools and spa with access to our outdoor patio and firepit. Available for hotel guests from 6 am - 10 pm.
  • Affordable Suburban property
More Photos Swimming pool at Courtyard by Marriott Boston Dedham / Westwood
From$80
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn Braintree 215 Wood Rd., Braintree, MA 02184
Call Us
~16.92 miles south of Winchester
  • Pool available: Indoor Pool and hot tub. 7am-10pm
  • 3-star Highway property
More Photos Photo of Hampton Inn Braintree Pool
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details

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