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.
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Winchester Hotels with Outdoor or Indoor Pools

Hampton Inn & Homewood Suites by Hilton Boston Woburn 371 Washington St., Woburn, MA 01801
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~0.63 miles northeast of Winchester
  • Pool available: Indoor Salt-Water Infused Pool
  • Three Star Suburban hotel
More Photos Pool image of Hampton Inn & Homewood Suites by Hilton Boston Woburn
From$166 total
Average 3.0 /5 Latest Reviews Call BookMore Details
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Best Western Plus New Englander - Woburn 1 Rainin Rd., Woburn, MA 01801
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~1.99 miles northeast of Winchester
  • Has swimming pool: Indoor heated pool Open 6 am - 10 pm
  • Affordable Suburban property
More Photos Swimming pool at Best Western Plus New Englander
From$86 total
Average 3.5 /5 Hotel Reviews Call BookMore Details
Hilton Boston / Woburn - Woburn 2 Forbes Rd., Woburn, MA 01801
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~2.86 miles north of Winchester
  • Pool details: Indoor
  • 3-star Suburban hotel
More Photos Pool image of Hilton Boston / Woburn
From$94 total
Very Good 4.0 /5 Review Score Call BookMore Details
Hampton Inn Woburn Boston : 371a Washington St. 371a Washington St., Woburn, MA 01801
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~3.00 miles north of Winchester
  • Pool details: Indoor Salt-Water Infused Pool
  • 3 star Suburban property
More Photos Swimming pool at Hampton Inn Woburn Boston
From$154 total
Average 3.0 /5 Read Reviews Call BookMore Details
Hyatt Place Boston / Medford 116 Riverside Ave., Medford, MA 02155
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~3.11 miles southeast of Winchester
  • Pool details: Our indoor pool is open between the hours of 6:00AM and 10:00PM.
  • Mid-scale Suburban hotel
More Photos Photo of Hyatt Place Boston / Medford Pool
From$106 total
Very Good 4.0 /5 Reviews Call BookMore Details
Fairfield Inn Boston Woburn / Burlington in Woburn 285 Mishawum Rd., Woburn, MA 01801
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~3.32 miles north of Winchester
  • Includes a pool: Seasonal outdoor pool
  • 3-star Highway hotel
More Photos Photo of Fairfield Inn Boston Woburn / Burlington Pool
From$76 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
HYATT house Boston/Burlington - Burlington 2 Van De Graaff Dr., Burlington, MA 01803
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~3.50 miles northwest of Winchester
  • Has swimming pool: The hotel pool is open seasonally from Memorial Day to Labor Day. It is open from 10am-10pm weather dependent during that time.
  • 3 star Suburban property
More Photos Photo of HYATT house Boston/Burlington Pool
From$50 total
Very Good 4.5 /5 Latest Reviews Call BookMore Details
AC Hotel Boston Cambridge in Cambridge 10 Acorn Park Dr., Cambridge, MA 02140
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~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$96 total
Average 3.0 /5 Reviews Call BookMore Details
Residence Inn by Marriott Boston Woburn 300 Presidential Way, Woburn, MA 01801
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~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 hotel
More Photos Photo of Residence Inn by Marriott Boston Woburn Pool
From$132 total
Very Good 4.0 /5 Review Score Call BookMore Details
AC Hotel by Marriott Boston North in Medford 95 Station Landing, Medford, MA 02155
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~4.65 miles southeast of Winchester
  • Pool details: Our indoor salt water pool is open from 7:00AM - 10:00PM.
  • Three Star Suburban property
More Photos Swimming pool at AC Hotel by Marriott Boston North
From$160 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Boston Cambridge Area in Somerville 30 Washington St., Somerville, MA 02143
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~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 Swimming pool at Holiday Inn Boston Cambridge Area
From$96 total
Average 3.0 /5 Latest Reviews Call BookMore Details
Element Lexington : 727 B Marrett Rd. 727 B Marrett Rd., Lexington, MA 02421
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~6.29 miles west of Winchester
  • Has swimming pool: 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.
  • Midscale Suburban property
More Photos Pool image of Element Lexington
From$96 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Aloft by Marriott Lexington - Lexington 727 a Marrett Rd., Lexington, MA 02421
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~6.29 miles west of Winchester
  • Includes a pool: 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
  • Affordable Suburban hotel
More Photos Pool image of Aloft by Marriott Lexington
From$91 total
Very Good 4.0 /5 Reviews Call BookMore Details
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Homewood Suites by Hilton Boston Billerica / Bedford / Burlington in Billerica 35 Middlesex Turnpike, Billerica, MA 01821
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~6.30 miles northwest of Winchester
  • With a pool!
  • Affordable Suburban hotel
More Photos Photo of Homewood Suites by Hilton Boston Billerica / Bedford / Burlington Pool
From$96 total
Average 3.0 /5 Read Reviews Call BookMore Details
Doubletree by Hilton Boston Logan Airport Chelsea : 201 Everett Ave. 201 Everett Ave., Chelsea, MA 02150
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~6.35 miles southeast of Winchester
  • Pool available: Visit our indoor heated pool. Open daily.
  • Midscale Airport property
More Photos Swimming pool at Doubletree by Hilton Boston Logan Airport Chelsea
From$96 total
Average 3.0 /5 Review Score Call BookMore Details
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Homewood Suites Boston Logan Airport Chelsea 145 Beech St., Chelsea, MA 02150
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~6.36 miles southeast of Winchester
  • Includes a pool: Indoor Heated Salt Water Pool- 7am to 10pm
  • 3 star Airport hotel
More Photos Pool image of Homewood Suites Boston Logan Airport Chelsea
From$96 total
Average 3.0 /5 Read Reviews Call BookMore Details
Residence Inn Boston Logan Airport/Chelsea : 200 a Maple St. 200 a Maple St., Chelsea, MA 02150
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~6.40 miles southeast of Winchester
  • Has swimming pool: Our Indoor heated saltwater pool is open from 10am to 10pm
  • Midscale Downtown hotel
More Photos Swimming pool at Residence Inn Boston Logan Airport/Chelsea
From$154 total
Average 3.0 /5 Reviews Call BookMore Details
Residence Inn Boston Watertown in Watertown 570 Arsenal St., Watertown, MA 02472
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~6.44 miles south of Winchester
  • Pool details: Indoor, heated pool is open daily from 8AM - 11PM.
  • 3 star Suburban property
More Photos Photo of Residence Inn Boston Watertown Pool
From$154 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Four Points by Sheraton Boston Logan Airport Revere : 407 Squire Rd. 407 Squire Rd., Revere, MA 02151
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~6.47 miles east of Winchester
  • Pool available: 6am - 10pm, indoor heated pool
  • 3-star Airport hotel
More Photos Photo of Four Points by Sheraton Boston Logan Airport Revere Pool
From$178 total
Average 3.0 /5 Read Reviews Call BookMore Details
Boston Marriott Cambridge in Cambridge 2 Cambridge Center 50 Broadway, Cambridge, MA 02142
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~6.86 miles southeast of Winchester
  • Pool in hotel
  • High-end Downtown hotel
More Photos Pool image of Boston Marriott Cambridge
From$180 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
The Royal Sonesta Boston : 40 Edwin Land Blvd. 40 Edwin Land Blvd., Cambridge, MA 02142
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~6.88 miles southeast of Winchester
  • Pool details: 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.
  • Four star Downtown hotel
More Photos Photo of The Royal Sonesta Boston Pool
From$120 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Residence Inn by Marriott Boston Harbor on Tudor Wharf - Boston 34 44 Charles River Ave., Boston, MA 02129
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~7.06 miles southeast of Winchester
  • Pool details: Take a splash in our indoor heated pool overlooking Boston Harbor. Open daily from 6am - 10pm and complimentary for all hotel guests.
  • Affordable Oceanfront property
More Photos Pool image of Residence Inn by Marriott Boston Harbor on Tudor Wharf
From$96 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Four Points by Sheraton Boston Newton 320 Washington St., Newton, MA 02458
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~7.27 miles south of Winchester
  • Pool available: 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.
  • Mid-scale Suburban property
More Photos Photo of Four Points by Sheraton Boston Newton Pool
From$118 total
Average 3.5 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Boston/Waltham 450 Totten Pond Rd., Waltham, MA 02451
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~7.30 miles southwest of Winchester
  • Pool available: Indoor pool open daily from 7am - 10pm.
  • Midscale Highway hotel
More Photos Swimming pool at Hilton Garden Inn Boston/Waltham
From$98 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Best Western Plus Waltham Boston 380 Winter St., Waltham, MA 02451
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~7.33 miles southwest of Winchester
  • With a pool!
  • Mid-scale hotel
More Photos Pool image of Best Western Plus Waltham Boston
From$102 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Wyndham Boston Beacon Hill in Boston 5 Blossom St., Boston, MA 02114
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~7.39 miles southeast of Winchester
  • Pool in hotel: Seasonal outdoor pool, typically open Memorial Day to Labor Day.
  • Four-star Downtown hotel
More Photos Swimming pool at Wyndham Boston Beacon Hill
From$150 total
Average 3.0 /5 Latest Reviews Call BookMore Details
HYATT house Boston/Waltham in Waltham 54 4th Ave., Waltham, MA 02451
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~7.42 miles southwest of Winchester
  • Pool details: Heated outdoor pool open Memorial Day through Labor Day.
  • Mid-scale Suburban property
More Photos Photo of HYATT house Boston/Waltham Pool
From$96 total
Average 3.0 /5 Recent Reviews Call BookMore Details
TownePlace Suites Boston Logan Airport/Chelsea - Chelsea 30 Eastern Ave., Chelsea, MA 02150
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~7.42 miles southeast of Winchester
  • Pool available: Indoor Heated Saltwater Pool open from 7AM to 10PM.
  • Midscale Airport property
More Photos Photo of TownePlace Suites Boston Logan Airport/Chelsea Pool
From$96 total
Average 3.0 /5 Latest Reviews Call BookMore Details
The Westin Waltham Boston - Waltham 70 3rd Ave., Waltham, MA 02451
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~7.50 miles southwest of Winchester
  • Pool details: 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 Swimming pool at The Westin Waltham Boston
From$130 total
Average 3.0 /5 Review Score Call BookMore Details
Hampton Inn Boston - Logan Airport : 230 Lee Burbank Highway 230 Lee Burbank Highway, Revere, MA 02151
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~7.64 miles east of Winchester
  • Includes a pool: Indoor pool, open 8AM-8PM
  • 3 star Airport hotel
More Photos Swimming pool at Hampton Inn Boston - Logan Airport
From$100 total
Average 3.0 /5 Reviews Call BookMore Details
Embassy Suites by Hilton Boston Waltham - Waltham 550 Winter St., Waltham, MA 02451
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~7.73 miles southwest of Winchester
  • Has swimming pool: 7am to 9pm Daily 40 x 20 Indoor
  • Mid-scale Suburban hotel
More Photos Swimming pool at Embassy Suites by Hilton Boston Waltham
From$96 total
Average 3.0 /5 Guest Reviews Call BookMore Details
The Arcadian Hotel 1200 Beacon St., Brookline, MA 02446
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~7.75 miles south of Winchester
  • Pool in hotel: Heated indoor saltwater pool and hot tub, 9am-9pm
  • 3-star Downtown property
More Photos Photo of The Arcadian Hotel Pool
From$96 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Residence Inn by Marriott Back Bay / Fenway 125 Brookline Ave., Boston, MA 02215
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~7.78 miles south of Winchester
  • Pool in hotel: Indoor pool located on our Rooftop Terrace Open from 7am - 9:30pm
  • Mid-scale Downtown property
More Photos Pool image of Residence Inn by Marriott Back Bay / Fenway
From$190 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Boston / Waltham in Waltham 135 2nd Ave., Waltham, MA 02451
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~7.86 miles southwest of Winchester
  • Pool available: Indoor Heated Pool
  • 3-star Suburban hotel
More Photos Pool image of Hampton Inn & Suites Boston / Waltham
From$96 total
Average 3.0 /5 Latest Reviews Call BookMore Details
The Verb Hotel 1271 Boylston St., Boston, MA 02215
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~7.87 miles south of Winchester
  • Pool in hotel: Open 8 AM to 10 PM. Open Year Round- Heated outdoor pool
  • High end Downtown property
More Photos Photo of The Verb Hotel Pool
From$130 total
Very Good 4.5 /5 Read Reviews Call BookMore Details
Boston Marriott Long Wharf - Boston 296 State St., Boston, MA 02109
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~7.92 miles southeast of Winchester
  • Has swimming pool
  • High-end Downtown hotel
More Photos Swimming pool at Boston Marriott Long Wharf
From$334 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Four Seasons Hotel Boston 200 Boylston St., Boston, MA 02116
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~7.93 miles southeast of Winchester
  • We have a pool ready for use
  • Luxury Five Star Downtown property
More Photos Photo of Four Seasons Hotel Boston Pool
From$354 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Courtyard by Marriott Boston Brookline 40 Webster St., Brookline, MA 02446
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~7.93 miles south of Winchester
  • Has swimming pool: 8am-10pm, indoor lap pool. Heated to utilize during the winter.
  • Mid-scale Downtown hotel
More Photos Photo of Courtyard by Marriott Boston Brookline Pool
From$96 total
Average 3.0 /5 Latest Reviews Call BookMore Details
Sheraton Boston a Marriott Hotel in Boston 39 Dalton St., Boston, MA 02199
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~7.98 miles south of Winchester
  • Includes a pool
  • High end Downtown hotel
More Photos Swimming pool at Sheraton Boston a Marriott Hotel
From$154 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Boston Harbor Hotel in Boston 70 Rowes Wharf, Boston, MA 02110
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~8.12 miles southeast of Winchester
  • Pool details: 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.
  • Luxury 5-star Downtown hotel
More Photos Swimming pool at Boston Harbor Hotel
From$390 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Homewood Suites by Hilton Boston Brookline-Longwood Medical 111 Boylston St., Brookline, MA 02445
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~8.61 miles south of Winchester
  • Has swimming pool: Our pool is currenlt closed due to the pandemic
  • Midscale Suburban hotel
More Photos Swimming pool at Homewood Suites by Hilton Boston Brookline-Longwood Medical
From$96 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Homewood Suites by Hilton Boston-Peabody 57 Newbury St., Peabody, MA 01960
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~8.76 miles northeast of Winchester
  • Pool available: Indoor pool 8 am to 10 pm
  • Affordable Highway property
More Photos Photo of Homewood Suites by Hilton Boston-Peabody Pool
From$106 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Seaport Hotel Boston 1 Seaport Lane, Boston, MA 02210
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~8.79 miles southeast of Winchester
  • Pool in hotel: Indoor Pool as part of Wave Fitness Health Club.
  • Expensive Convention Center property
More Photos Photo of Seaport Hotel Boston Pool
From$178 total
Very Good 4.0 /5 Reviews Call BookMore Details
The Westin Boston Seaport District 425 Summer St., Boston, MA 02210
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~8.79 miles southeast of Winchester
  • Has swimming pool
  • 4-star Convention Center property
More Photos Pool image of The Westin Boston Seaport District
From$214 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Renaissance Boston Seaport District in Boston 606 Congress St., Boston, MA 02210
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~8.97 miles southeast of Winchester
  • Has swimming pool
  • High end property
More Photos Pool image of Renaissance Boston Seaport District
From$192 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Courtyard by Marriott Boston Billerica / Bedford : 270 Concord Rd. 270 Concord Rd., Billerica, MA 01821
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~9.48 miles northwest of Winchester
  • Pool in hotel: The pool is 15x35 and 4'6" deep at the mid point. Hours are 6am - 11pm
  • 3-star Suburban property
More Photos Photo of Courtyard by Marriott Boston Billerica / Bedford Pool
From$99 total
Average 3.5 /5 Hotel Reviews Call BookMore Details
Boston Marriott Newton 2345 Commonwealth Ave., Newton, MA 02466
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~9.71 miles southwest of Winchester
  • Has swimming pool: Indoor pool
  • 3 star Suburban hotel
More Photos Photo of Boston Marriott Newton Pool
From$190 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Springhill Suites by Marriott Boston Peabody in Peabody 43 Newbury St., Peabody, MA 01960
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~9.97 miles northeast of Winchester
  • Includes a pool: Indoor pool & hot tub Open 7:00am - 11:00pm
  • Three Star Suburban hotel
More Photos Photo of Springhill Suites by Marriott Boston Peabody Pool
From$94 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Boston Marriott Peabody - Peabody 8a Centennial Dr., Peabody, MA 01960
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~10.08 miles east of Winchester
  • With a pool!
  • Expensive Suburban hotel
More Photos Pool image of Boston Marriott Peabody
From$150 total
Average 3.0 /5 Read Reviews Call BookMore Details
Candlewood Suites Boston North Shore Danvers by IHG 238 Andover St., Danvers, MA 01923
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~10.86 miles northeast of Winchester
  • Includes a pool: Outdoor pool open Memorial Day-Labor Day
  • Inexpensive Suburban hotel
More Photos Swimming pool at Candlewood Suites Boston North Shore Danvers by IHG
From$130 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details

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