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 in Woburn
+1-888-389-4121

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371 Washington St., Woburn, MA 01801 ~0.63 miles northeast of Winchester
  • Pool in hotel: Indoor Salt-Water Infused Pool
  • Affordable Suburban property
More Photos Swimming pool at Hampton Inn & Homewood Suites by Hilton Boston Woburn
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
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Best Western Plus New Englander - Woburn
+1-888-675-2083

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1 Rainin Rd., Woburn, MA 01801 ~1.99 miles northeast of Winchester
  • Pool details: Indoor heated pool Open 6 am - 10 pm
  • Midscale Suburban hotel
More Photos Pool image of Best Western Plus New Englander
From$72
Average 3.5 /5 Latest Reviews Call BookMore Details
Hilton Boston / Woburn - Woburn
+1-800-716-8490

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2 Forbes Rd., Woburn, MA 01801 ~2.86 miles north of Winchester
  • Pool details: Indoor
  • Mid-scale Suburban hotel
More Photos Swimming pool at Hilton Boston / Woburn
From$79
Very Good 4.0 /5 Review Score Call BookMore Details
Crowne Plaza Boston - Woburn by IHG
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
15 Middlesex Canal Park, Woburn, MA 01801 ~2.99 miles north of Winchester
  • Pool details: Open from 7am to 10pm. Reservations Required.
  • Expensive Suburban property
More Photos Photo of Crowne Plaza Boston - Woburn by IHG Pool
From$105
Very Good 4.0 /5 Reviews Call BookMore Details
Hampton Inn Woburn Boston
+1-888-965-1860

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371a Washington St., Woburn, MA 01801 ~3.00 miles north of Winchester
  • Pool in hotel: Indoor Salt-Water Infused Pool
  • Affordable Suburban property
More Photos Photo of Hampton Inn Woburn Boston Pool
From$129
Average 3.0 /5 Latest Reviews Call BookMore Details
Hyatt Place Boston/Medford in Medford
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
116 Riverside Ave., Medford, MA 02155 ~3.11 miles southeast of Winchester
  • Has swimming pool: Our indoor pool is open between the hours of 6:00AM and 10:00PM.
  • Mid-scale Suburban property
More Photos Pool image of Hyatt Place Boston/Medford
From$89
Very Good 4.0 /5 Reviews Call BookMore Details
Fairfield Inn Boston Woburn / Burlington
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
285 Mishawum Rd., Woburn, MA 01801 ~3.32 miles north of Winchester
  • Pool available: Seasonal outdoor pool
  • Mid-scale Highway hotel
More Photos Swimming pool at Fairfield Inn Boston Woburn / Burlington
From$64
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hyatt House Boston Burlington in Burlington
+1-888-311-4278

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2 Van De Graaff Dr., Burlington, MA 01803 ~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.
  • 3-star Suburban hotel
More Photos Swimming pool at Hyatt House Boston Burlington
From$42
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Boston Marriott Burlington in Burlington
+1-888-469-4795

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1 Burlington Mall Rd., Burlington, MA 01803 ~3.89 miles northwest of Winchester
  • Has swimming pool: Indoor Pool 6AM - 11PM Outdoor Pool 6AM - Dusk
  • High end Suburban property
More Photos Pool image of Boston Marriott Burlington
From$119
Very Good 4.0 /5 Reviews Call BookMore Details
AC Hotel Boston Cambridge in Cambridge
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
10 Acorn Park Dr., Cambridge, MA 02140 ~3.93 miles south of Winchester
  • Pool in hotel: Indoor heated salt water pool open from 7am to 10pm.
  • Mid-scale Suburban hotel
More Photos Pool image of AC Hotel Boston Cambridge
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Residence Inn by Marriott Boston Woburn
+1-888-841-5292

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300 Presidential Way, Woburn, MA 01801 ~4.50 miles north of Winchester
  • Has swimming pool: Heated indoor pool and whirlpool. Open 7 days a week from 6:00AM-10:00PM
  • 3 star Suburban hotel
More Photos Swimming pool at Residence Inn by Marriott Boston Woburn
From$110
Very Good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Boston Cambridge Area
+1-888-455-5160

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30 Washington St., Somerville, MA 02143 ~5.83 miles southeast of Winchester
  • Pool available: * 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 Recent Reviews Call BookMore Details
Element Lexington
+1-888-965-8297

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727 B Marrett Rd., Lexington, MA 02421 ~6.29 miles west of Winchester
  • Pool details: 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.
  • 3-star Suburban hotel
More Photos Photo of Element Lexington Pool
From$80
Average 3.0 /5 Review Score Call BookMore Details
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Aloft Lexington : 727 a Marrett Rd.
+1-888-906-6358

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727 a Marrett Rd., Lexington, MA 02421 ~6.29 miles west of Winchester
  • Pool available: 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
  • Mid-scale Suburban property
More Photos Pool image of Aloft Lexington
From$76
Very Good 4.0 /5 Read Reviews Call BookMore Details
Homewood Suites by Hilton Boston Billerica / Bedford / Burlington
+1-888-749-6785

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35 Middlesex Turnpike, Billerica, MA 01821 ~6.30 miles northwest of Winchester
  • Pool in hotel
  • 3-star Suburban hotel
More Photos Photo of Homewood Suites by Hilton Boston Billerica / Bedford / Burlington Pool
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
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Homewood Suites Boston Logan Airport Chelsea
+1-888-878-9982

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145 Beech St., Chelsea, MA 02150 ~6.36 miles southeast of Winchester
  • Pool in hotel: Indoor Heated Salt Water Pool- 7am to 10pm
  • Affordable Airport property
More Photos Photo of Homewood Suites Boston Logan Airport Chelsea Pool
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Residence Inn Boston Logan Airport / Chelsea
+1-888-389-4485

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200 a Maple St., Chelsea, MA 02150 ~6.40 miles southeast of Winchester
  • Pool details: Our Indoor heated saltwater pool is open from 10am to 10pm
  • Affordable Downtown hotel
More Photos Pool image of Residence Inn Boston Logan Airport / Chelsea
From$129
Average 3.0 /5 Guest Reviews Call BookMore Details
Residence Inn Boston Watertown : 570 Arsenal St.
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
570 Arsenal St., Watertown, MA 02472 ~6.44 miles south of Winchester
  • Has swimming pool: Indoor, heated pool is open daily from 8AM - 11PM.
  • Affordable Suburban hotel
More Photos Pool image of Residence Inn Boston Watertown
From$129
Average 3.0 /5 Hotel Reviews Call BookMore Details
Four Points by Sheraton Boston Logan Airport Revere - Revere
+1-888-675-2083

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407 Squire Rd., Revere, MA 02151 ~6.47 miles east of Winchester
  • Pool in hotel: 6am - 10pm, indoor heated pool
  • Affordable 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
Residence Inn by Marriott Boston Cambridge
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
120 Broadway Six Cambridge Center, Cambridge, MA 02142 ~6.75 miles south of Winchester
  • Our hotel comes with a pool
  • 3-star hotel
More Photos Pool image of Residence Inn by Marriott Boston Cambridge
From$279
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Four Points by Sheraton Boston Newton
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
320 Washington St., Newton, MA 02458 ~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.
  • 3 star 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 - Waltham
+1-888-965-1860

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450 Totten Pond Rd., Waltham, MA 02451 ~7.30 miles southwest of Winchester
  • Pool in hotel: Indoor pool open daily from 7am - 10pm.
  • Three Star Highway hotel
More Photos Swimming pool at Hilton Garden Inn Boston/Waltham
From$82
Very Good 4.0 /5 Review Score Call BookMore Details
Best Western Plus Waltham Boston
+1-888-788-5576

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380 Winter St., Waltham, MA 02451 ~7.33 miles southwest of Winchester
  • Includes a pool
  • Three Star property
More Photos Swimming pool at Best Western Plus Waltham Boston
From$86
Average 3.0 /5 Read Reviews Call BookMore Details
Wyndham Boston Beacon Hill
+1-888-897-9207

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5 Blossom St., Boston, MA 02114 ~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 Swimming pool at Wyndham Boston Beacon Hill
From$125
Average 3.0 /5 Latest Reviews Call BookMore Details
HYATT house Boston/Waltham - Waltham
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
54 4th Ave., Waltham, MA 02451 ~7.42 miles southwest of Winchester
  • Has swimming pool: 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 Review Score Call BookMore Details
TownePlace Suites Boston Logan Airport/Chelsea
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
30 Eastern Ave., Chelsea, MA 02150 ~7.42 miles southeast of Winchester
  • Pool available: Indoor Heated Saltwater Pool open from 7AM to 10PM.
  • Mid-scale Airport property
More Photos Photo of TownePlace Suites Boston Logan Airport/Chelsea Pool
From$80
Average 3.0 /5 Reviews Call BookMore Details
The Westin Waltham Boston in Waltham
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
70 3rd Ave., Waltham, MA 02451 ~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
  • Expensive Suburban property
More Photos Pool image of The Westin Waltham Boston
From$79
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Boston Logan Airport - Revere
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
230 Lee Burbank Highway, Revere, MA 02151 ~7.64 miles east of Winchester
  • Includes a pool: Indoor pool, open 8AM-8PM
  • Affordable Airport hotel
More Photos Photo of Hampton Inn Boston Logan Airport Pool
From$84
Average 3.0 /5 Hotel Reviews Call BookMore Details
Embassy Suites by Hilton Boston Waltham
+1-888-455-5160

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New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
550 Winter St., Waltham, MA 02451 ~7.73 miles southwest of Winchester
  • Pool available: 7am to 9pm Daily 40 x 20 Indoor
  • Midscale Suburban property
More Photos Pool image of Embassy Suites by Hilton Boston Waltham
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
The Arcadian Hotel
+1-888-965-8297

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1200 Beacon St., Brookline, MA 02446 ~7.75 miles south of Winchester
  • Includes a pool: Heated indoor saltwater pool and hot tub, 9am-9pm
  • 3-star Downtown hotel
More Photos Swimming pool at The Arcadian Hotel
From$80
Average 3.0 /5 Reviews Call BookMore Details
Residence Inn by Marriott Back Bay / Fenway : 125 Brookline Ave.
+1-888-906-6358

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125 Brookline Ave., Boston, MA 02215 ~7.78 miles south of Winchester
  • Pool details: 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$159
Very Good 4.0 /5 Review Score Call BookMore Details
Courtyard by Marriott Boston Brookline
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
40 Webster St., Brookline, MA 02446 ~7.93 miles south of Winchester
  • Includes a pool: 8am-10pm, indoor lap pool. Heated to utilize during the winter.
  • Midscale Downtown hotel
More Photos Pool image of Courtyard by Marriott Boston Brookline
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Hilton Boston Back Bay
+1-888-878-9982

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40 Dalton St., Boston, MA 02115 ~7.97 miles south of Winchester
  • Pool details: yes
  • Four star Convention Center property
More Photos Photo of Hilton Boston Back Bay Pool
From$199
Average 3.0 /5 Hotel Reviews Call BookMore Details
The Langham Boston in Boston
+1-888-389-4485

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250 Franklin St., Boston, MA 02110 ~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
  • Luxury 5 star Downtown property
More Photos Pool image of The Langham Boston
From$160
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Doubletree Downtown
+1-888-389-4121

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821 Washington St., Boston, MA 02111 ~8.23 miles southeast of Winchester
  • Includes a pool
  • 3-star Downtown property
More Photos Pool image of Doubletree Downtown
From$100
Average 3.0 /5 Recent Reviews Call BookMore Details
Homewood Suites by Hilton Boston Brookline-Longwood Medical : 111 Boylston St.
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
111 Boylston St., Brookline, MA 02445 ~8.61 miles south of Winchester
  • Includes a pool: Our pool is currenlt closed due to the pandemic
  • Mid-scale Suburban hotel
More Photos Pool image of Homewood Suites by Hilton Boston Brookline-Longwood Medical
From$80
Very Good 4.0 /5 Reviews Call BookMore Details
Homewood Suites by Hilton Boston-Peabody : 57 Newbury St.
+1-800-716-8490

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57 Newbury St., Peabody, MA 01960 ~8.76 miles northeast of Winchester
  • Includes a pool: Indoor pool 8 am to 10 pm
  • 3 star Highway hotel
More Photos Pool image of 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.
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
270 Concord Rd., Billerica, MA 01821 ~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
  • Midscale Suburban property
More Photos Pool image of Courtyard by Marriott Boston Billerica / Bedford
From$83
Average 3.5 /5 Review Score Call BookMore Details
Springhill Suites by Marriott Boston Peabody
+1-888-965-1860

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43 Newbury St., Peabody, MA 01960 ~9.97 miles northeast of Winchester
  • Pool available: Indoor pool & hot tub Open 7:00am - 11:00pm
  • Three Star Suburban hotel
More Photos Swimming pool at Springhill Suites by Marriott Boston Peabody
From$79
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Boston Marriott Peabody
+1-888-788-5576

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8a Centennial Dr., Peabody, MA 01960 ~10.08 miles east of Winchester
  • Includes a swimming pool
  • Expensive Suburban hotel
More Photos Swimming pool at Boston Marriott Peabody
From$125
Average 3.0 /5 Recent Reviews Call BookMore Details
Candlewood Suites Boston North Shore Danvers by IHG - Danvers
+1-888-897-9207

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238 Andover St., Danvers, MA 01923 ~10.86 miles northeast of Winchester
  • Pool details: Outdoor pool open Memorial Day-Labor Day
  • Two-star Suburban hotel
More Photos Swimming pool at Candlewood Suites Boston North Shore Danvers by IHG
From$109
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Best Western Plus North Shore Hotel : 50 Dayton St.
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
50 Dayton St., Danvers, MA 01923 ~11.41 miles northeast of Winchester
  • Includes a pool: Indoor Heated Pool
  • Affordable Suburban hotel
More Photos Swimming pool at Best Western Plus North Shore Hotel
From$82
Very Good 4.0 /5 Review Score Call BookMore Details
Homewood Suites by Hilton Needham Boston
+1-888-469-4795

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200 1st Ave., Needham, MA 02494 ~11.49 miles southwest of Winchester
  • Has swimming pool: Indoor pool 7:00am - 10:00pm.
  • 3-star Suburban hotel
More Photos Swimming pool at Homewood Suites by Hilton Needham Boston
From$139
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Sonesta Select Boston Danvers
+1-888-734-9421

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275 Independence Way, Danvers, MA 01923 ~12.26 miles northeast of Winchester
  • Has swimming pool: Outdoor Pool - Summer Seasonal
  • 3 star Suburban hotel
More Photos Photo of Sonesta Select Boston Danvers Pool
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Doubletree by Hilton Boston North Shore
+1-888-841-5292

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50 Ferncroft Rd., Danvers, MA 01923 ~12.97 miles northeast of Winchester
  • Pool details: Hours of Operations from 6:00AM - 10:00PM.
  • 3 star Suburban hotel
More Photos Pool image of Doubletree by Hilton Boston North Shore
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Hampton Inn - Salem
+1-888-455-5160

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11 Dodge St., Salem, MA 01970 ~13.11 miles east of Winchester
  • Has swimming pool: Large Indoor Salt Water Pool
  • Two-star Downtown property
More Photos Pool image of Hampton Inn
From$60
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Sonesta Select Boston Lowell Chelmsford
+1-888-965-8297

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30 Industrial Ave. East, Lowell, MA 01852 ~14.36 miles northwest of Winchester
  • Pool in hotel: Currently not open
  • Midscale Suburban property
More Photos Pool image of Sonesta Select Boston Lowell Chelmsford
From$119
Very Good 4.0 /5 Review Score Call BookMore Details
Hampton Inn & Suites Westford-Chelmsford : 9 Nixon Rd.
+1-888-906-6358

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9 Nixon Rd., Westford, MA 01886 ~16.44 miles northwest of Winchester
  • Includes a pool: Indoor Pool- 6am to 10pm
  • Mid-scale Suburban hotel
More Photos Photo of Hampton Inn & Suites Westford-Chelmsford Pool
From$89
Very Good 4.0 /5 Review Score Call BookMore Details
Courtyard by Marriott Boston Dedham / Westwood
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
64 University Ave., Westwood, MA 02090 ~16.86 miles south of Winchester
  • Includes a pool: There is 2 indoor pools and spa with access to our outdoor patio and firepit. Available for hotel guests from 6 am - 10 pm.
  • 3-star Suburban hotel
More Photos Photo of Courtyard by Marriott Boston Dedham / Westwood Pool
From$80
Very Good 4.0 /5 Read Reviews Call BookMore Details
Residence Inn by Marriott Boston Andover
+1-888-878-9982

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
500 Minuteman Rd., Andover, MA 01810 ~17.09 miles north of Winchester
  • Pool available: May - september seasonal
  • Midscale Suburban hotel
More Photos Pool image of Residence Inn by Marriott Boston Andover
From$70
Very Good 4.0 /5 Recent Reviews Call BookMore Details

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