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
  • Includes a pool: Indoor Salt-Water Infused Pool
  • 3-star Suburban property
More Photos Swimming pool at Hampton Inn & Homewood Suites by Hilton Boston Woburn
From$139
Average 3.0 /5 Read 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
  • Pool in hotel: Indoor heated pool Open 6 am - 10 pm
  • 3 star Suburban property
More Photos Photo of Best Western Plus New Englander Pool
From$72
Average 3.5 /5 Latest Reviews Call BookMore Details
Hilton Boston / Woburn in Woburn 2 Forbes Rd., Woburn, MA 01801
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~2.86 miles north of Winchester
  • Pool available: Indoor
  • Midscale Suburban property
More Photos Photo of Hilton Boston / Woburn Pool
From$79
Very Good 4.0 /5 Read Reviews Call BookMore Details
Crowne Plaza Boston - Woburn by IHG : 15 Middlesex Canal Park 15 Middlesex Canal Park, Woburn, MA 01801
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~2.99 miles north of Winchester
  • Pool in hotel: Open from 7am to 10pm. Reservations Required.
  • Expensive Suburban property
More Photos Pool image of Crowne Plaza Boston - Woburn by IHG
From$105
Very Good 4.0 /5 Reviews Call BookMore Details
Hampton Inn Woburn Boston 371a Washington St., Woburn, MA 01801
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~3.00 miles north of Winchester
  • Pool in hotel: Indoor Salt-Water Infused Pool
  • 3 star Suburban hotel
More Photos Pool image of Hampton Inn Woburn Boston
From$129
Average 3.0 /5 Recent 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 available: Our indoor pool is open between the hours of 6:00AM and 10:00PM.
  • 3 star Suburban hotel
More Photos Pool image of Hyatt Place Boston/Medford
From$89
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Fairfield Inn Boston Woburn / Burlington 285 Mishawum Rd., Woburn, MA 01801
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~3.32 miles north of Winchester
  • Pool in hotel: Seasonal outdoor pool
  • Affordable Highway property
More Photos Swimming pool at Fairfield Inn Boston Woburn / Burlington
From$64
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hyatt House Boston Burlington 2 Van De Graaff Dr., Burlington, MA 01803
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~3.50 miles northwest of Winchester
  • Pool in hotel: 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 Swimming pool at Hyatt House Boston Burlington
From$42
Very Good 4.5 /5 Latest Reviews Call BookMore Details
AC Hotel Boston Cambridge 10 Acorn Park Dr., Cambridge, MA 02140
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~3.93 miles south of Winchester
  • Pool available: Indoor heated salt water pool open from 7am to 10pm.
  • Midscale Suburban property
More Photos Photo of AC Hotel Boston Cambridge Pool
From$80
Average 3.0 /5 Reviews Call BookMore Details
Residence Inn by Marriott Boston Woburn in Woburn 300 Presidential Way, Woburn, MA 01801
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~4.50 miles north of Winchester
  • Pool details: Heated indoor pool and whirlpool. Open 7 days a week from 6:00AM-10:00PM
  • Affordable Suburban property
More Photos Swimming pool at Residence Inn by Marriott Boston Woburn
From$110
Very Good 4.0 /5 Recent 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
  • Has swimming 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 property
More Photos Pool image of Holiday Inn Boston Cambridge Area
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Element Lexington - Lexington 727 B Marrett Rd., Lexington, MA 02421
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~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 Review Score Call BookMore Details
Aloft Lexington 727 a Marrett Rd., Lexington, MA 02421
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~6.29 miles west of Winchester
  • Has swimming 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 property
More Photos Swimming pool at Aloft Lexington
From$76
Very Good 4.0 /5 Reviews Call BookMore Details
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Homewood Suites by Hilton Boston Billerica / Bedford / Burlington - Billerica 35 Middlesex Turnpike, Billerica, MA 01821
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~6.30 miles northwest of Winchester
  • We have a pool
  • Mid-scale Suburban hotel
More Photos Pool image of Homewood Suites by Hilton Boston Billerica / Bedford / Burlington
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Doubletree by Hilton Boston Logan Airport Chelsea 201 Everett Ave., Chelsea, MA 02150
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~6.35 miles southeast of Winchester
  • Pool in hotel: Visit our indoor, heated pool. Open from 7am - 10pm
  • 3 star Airport hotel
More Photos Pool image of Doubletree by Hilton Boston Logan Airport Chelsea
From$80
Average 3.0 /5 Reviews 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
  • Pool available: Indoor Heated Salt Water Pool- 7am to 10pm
  • 3-star Airport hotel
More Photos Photo of Homewood Suites Boston Logan Airport Chelsea Pool
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Residence Inn Boston Logan Airport/Chelsea 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
  • Three Star Downtown property
More Photos Pool image of Residence Inn Boston Logan Airport/Chelsea
From$129
Average 3.0 /5 Latest 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 available: Indoor, heated pool is open daily from 8AM - 11PM.
  • Mid-scale Suburban hotel
More Photos Photo of Residence Inn Boston Watertown Pool
From$129
Average 3.0 /5 Recent Reviews Call BookMore Details
Four Points by Sheraton Boston Logan Airport Revere 407 Squire Rd., Revere, MA 02151
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~6.47 miles east of Winchester
  • Pool in hotel: 6am - 10pm, indoor heated pool
  • 3-star Airport hotel
More Photos Photo of Four Points by Sheraton Boston Logan Airport Revere Pool
From$149
Average 3.0 /5 Latest Reviews Call BookMore Details
Boston Marriott Cambridge : 2 Cambridge Center 50 Broadway 2 Cambridge Center 50 Broadway, Cambridge, MA 02142
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~6.86 miles southeast of Winchester
  • Has swimming pool
  • 4-star Downtown hotel
More Photos Photo of Boston Marriott Cambridge Pool
From$150
Very Good 4.0 /5 Latest Reviews Call BookMore Details
The Royal Sonesta Boston 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.
  • Expensive Downtown property
More Photos Swimming pool at The Royal Sonesta Boston
From$100
Very Good 4.0 /5 Recent 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 in hotel: Take a splash in our indoor heated pool overlooking Boston Harbor. Open daily from 6am - 10pm and complimentary for all hotel guests.
  • Mid-scale Oceanfront hotel
More Photos Photo of Residence Inn by Marriott Boston Harbor on Tudor Wharf Pool
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Four Points by Sheraton Boston Newton : 320 Washington St. 320 Washington St., Newton, MA 02458
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~7.27 miles south of Winchester
  • Pool details: 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.
  • Midscale Suburban property
More Photos Pool image of Four Points by Sheraton Boston Newton
From$99
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
  • Has swimming pool: Indoor pool open daily from 7am - 10pm.
  • Three Star Highway property
More Photos Swimming pool at Hilton Garden Inn Boston/Waltham
From$82
Very Good 4.0 /5 Reviews Call BookMore Details
Best Western Plus Waltham Boston in Waltham 380 Winter St., Waltham, MA 02451
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~7.33 miles southwest of Winchester
  • Includes a swimming pool
  • Midscale property
More Photos Pool image of Best Western Plus Waltham Boston
From$85
Average 3.0 /5 Read Reviews Call BookMore Details
Wyndham Boston Beacon Hill : 5 Blossom St. 5 Blossom St., Boston, MA 02114
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~7.39 miles southeast of Winchester
  • Has swimming pool: Seasonal outdoor pool, typically open Memorial Day to Labor Day.
  • High-end Downtown property
More Photos Pool image of Wyndham Boston Beacon Hill
From$125
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 in hotel: Heated outdoor pool open Memorial Day through Labor Day.
  • 3-star Suburban property
More Photos Pool image of HYATT house Boston/Waltham
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
TownePlace Suites Boston Logan Airport/Chelsea in Chelsea 30 Eastern Ave., Chelsea, MA 02150
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~7.42 miles southeast of Winchester
  • Has swimming pool: Indoor Heated Saltwater Pool open from 7AM to 10PM.
  • 3-star Airport hotel
More Photos Photo of TownePlace Suites Boston Logan Airport/Chelsea Pool
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
The Westin Waltham Boston : 70 3rd Ave. 70 3rd Ave., Waltham, MA 02451
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~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
  • High-end Suburban property
More Photos Photo of The Westin Waltham Boston Pool
From$109
Average 3.0 /5 Hotel Reviews 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
  • Pool details: Indoor pool, open 8AM-8PM
  • Affordable Airport hotel
More Photos Photo of Hampton Inn Boston - Logan Airport Pool
From$84
Average 3.0 /5 Reviews Call BookMore Details
Embassy Suites by Hilton Boston Waltham : 550 Winter St. 550 Winter St., Waltham, MA 02451
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~7.73 miles southwest of Winchester
  • Pool available: 7am to 9pm Daily 40 x 20 Indoor
  • Affordable Suburban hotel
More Photos Pool image of Embassy Suites by Hilton Boston Waltham
From$80
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The Arcadian Hotel - Brookline 1200 Beacon St., Brookline, MA 02446
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~7.75 miles south of Winchester
  • Pool details: Heated indoor saltwater pool and hot tub, 9am-9pm
  • Mid-scale Downtown hotel
More Photos Photo of The Arcadian Hotel Pool
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Residence Inn by Marriott Back Bay / Fenway - Boston 125 Brookline Ave., Boston, MA 02215
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~7.78 miles south of Winchester
  • Has swimming pool: 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 Guest Reviews Call BookMore Details
Hampton Inn & Suites Boston / Waltham 135 2nd Ave., Waltham, MA 02451
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~7.86 miles southwest of Winchester
  • Has swimming pool: Indoor Heated Pool
  • 3-star Suburban property
More Photos Swimming pool at Hampton Inn & Suites Boston / Waltham
From$80
Average 3.0 /5 Reviews Call BookMore Details
The Verb Hotel : 1271 Boylston St. 1271 Boylston St., Boston, MA 02215
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~7.87 miles south of Winchester
  • Pool available: Open 8 AM to 10 PM. Open Year Round- Heated outdoor pool
  • 4-star Downtown hotel
More Photos Pool image of The Verb Hotel
From$109
Very Good 4.5 /5 Review Score Call BookMore Details
Boston Marriott Long Wharf in Boston 296 State St., Boston, MA 02109
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~7.92 miles southeast of Winchester
  • Pool in hotel
  • Expensive Downtown property
More Photos Swimming pool at Boston Marriott Long Wharf
From$279
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Four Seasons Hotel Boston in Boston 200 Boylston St., Boston, MA 02116
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~7.93 miles southeast of Winchester
  • Has swimming pool
  • Luxury Five Star Downtown hotel
More Photos Swimming pool at Four Seasons Hotel Boston
From$295
Very Good 4.0 /5 Guest 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 Pool image of Courtyard by Marriott Boston Brookline
From$80
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Sheraton Boston a Marriott Hotel in Boston 39 Dalton St., Boston, MA 02199
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~7.98 miles south of Winchester
  • We have a pool ready for use
  • Four-star Downtown hotel
More Photos Swimming pool at Sheraton Boston a Marriott Hotel
From$129
Very Good 4.0 /5 Reviews Call BookMore Details
Boston Harbor Hotel 70 Rowes Wharf, Boston, MA 02110
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~8.12 miles southeast of Winchester
  • Pool in hotel: 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 5 Star Downtown property
More Photos Pool image of Boston Harbor Hotel
From$325
Very Good 4.0 /5 Reviews Call BookMore Details
Homewood Suites by Hilton Boston Brookline-Longwood Medical : 111 Boylston St. 111 Boylston St., Brookline, MA 02445
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~8.61 miles south of Winchester
  • Pool details: Our pool is currenlt closed due to the pandemic
  • 3-star Suburban property
More Photos Photo of Homewood Suites by Hilton Boston Brookline-Longwood Medical Pool
From$80
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Homewood Suites by Hilton Boston-Peabody : 57 Newbury St. 57 Newbury St., Peabody, MA 01960
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~8.76 miles northeast of Winchester
  • Pool in hotel: Indoor pool 8 am to 10 pm
  • Midscale Highway property
More Photos Photo of Homewood Suites by Hilton Boston-Peabody Pool
From$89
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Seaport Hotel Boston in Boston 1 Seaport Lane, Boston, MA 02210
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~8.79 miles southeast of Winchester
  • Includes a pool: Indoor Pool as part of Wave Fitness Health Club.
  • High-end Convention Center hotel
More Photos Swimming pool at Seaport Hotel Boston
From$149
Very Good 4.0 /5 Latest 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
  • Includes a pool
  • 4 star Convention Center hotel
More Photos Photo of The Westin Boston Seaport District Pool
From$179
Very Good 4.0 /5 Review Score 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
  • Includes a swimming pool
  • Four star hotel
More Photos Pool image of Renaissance Boston Seaport District
From$160
Very Good 4.0 /5 Reviews Call BookMore Details
Boston Marriott Newton 2345 Commonwealth Ave., Newton, MA 02466
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~9.71 miles southwest of Winchester
  • Pool details: Indoor pool
  • Affordable Suburban property
More Photos Photo of Boston Marriott Newton Pool
From$159
Very Good 4.0 /5 Reviews Call BookMore Details
Springhill Suites by Marriott Boston Peabody : 43 Newbury St. 43 Newbury St., Peabody, MA 01960
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~9.97 miles northeast of Winchester
  • Pool details: Indoor pool & hot tub Open 7:00am - 11:00pm
  • Affordable Suburban property
More Photos Pool image of Springhill Suites by Marriott Boston Peabody
From$79
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Boston Marriott Peabody : 8a Centennial Dr. 8a Centennial Dr., Peabody, MA 01960
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~10.08 miles east of Winchester
  • Our hotel comes with a pool
  • 4 star Suburban property
More Photos Swimming pool at Boston Marriott Peabody
From$125
Average 3.0 /5 Hotel Reviews Call BookMore Details
Candlewood Suites Boston North Shore Danvers by IHG : 238 Andover St. 238 Andover St., Danvers, MA 01923
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~10.86 miles northeast of Winchester
  • Pool available: Outdoor pool open Memorial Day-Labor Day
  • Two-star Suburban hotel
More Photos Pool image of Candlewood Suites Boston North Shore Danvers by IHG
From$109
Very Good 4.0 /5 Reviews Call BookMore Details
Sheraton Boston Needham Hotel - Needham 100 Cabot St., Needham, MA 02494
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~11.35 miles southwest of Winchester
  • Pool available: Relax in our indoor headted wimming pool and jacuzzi. Our swimming area alos offers an outside deck for sunbathing and enjoying the warm weather in the summer months. We offer Sheraton Fitness Programmed by Core Performance, which includes stairmasters, treadmills, free weights and cardiovascular machines. Pool and Fitness hours 6:30AM ~ 10:30PM
  • 3-star Suburban hotel
More Photos Photo of Sheraton Boston Needham Hotel Pool
From$119
Average 3.0 /5 Reviews Call BookMore Details

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