Winchester Massachusetts Hotels & Motels

Find hotels in Winchester using the list and search tools below. Search for cheap and discounted hotel and motel rates in or near Winchester, MA for your corporate or personal leisure travel. We show the best Winchester, Massachusetts hotel and motel rooms. Browse the Winchester area hotels to find the perfect lodging! Please use the provided map of the Winchester hotels. Booking 5+ Rooms? Find Winchester Group Hotel Discounts

The Winchester center point is about 2 miles northeast of Arlington Center and 3 miles north of East Arlington.

Winchester is a fascinating, historic New England town located just north of Boston. With its quaint shops, lovely parks, and friendly people, Winchester is the hot spot to visit for a day or a weekend. It is filled with beautiful Victorian homes and tree-lined streets. There are plenty of things to do in Winchester, from hiking and biking trails to shopping and dining. For history buffs, the Winchester Historical Society offers guided tours of the area. For those who enjoy the outdoors, the area has several beautiful parks, including the Mystic Lakes State Park and the Brooks Parkhurst Town Forest. And for shoppers, the city center offers a range of unique stores. Winchester hosts plenty of annual events, including the Winchester Farmers' Market. The market features local farmers and vendors selling fresh produce, flowers, and other goods. When choosing a place to stay in Winchester, MA, be sure to check out the hotels, inns, and suites in the area. These lodgings offer a multitude of amenities that are sure to make your time in Winchester enjoyable and comfortable. There are a whole lot of options available to suit any budget or need. Many of the local lodgings offer on-site restaurants, fitness centers, pools, and more. All of the lodgings in Winchester are designed with your comfort in mind, so you can be sure you'll have a pleasant time. If you're looking for a convenient location, comfortable room, or first-rate amenities, there is a top-notch option for your stay. More from this guide...

Winchester Hotels/Accommodations

Hampton Inn Boston Woburn - Woburn 371a Washington St., Woburn, MA 01801 Call ~0.63 miles northeast of Winchester
  • Midscale Suburban property
  • 5 floors in hotel
From£56
Very good 4.0 /5 Recent Reviews Call BookMore Details
Hampton Inn & Homewood Suites by Hilton Boston Woburn 371 Washington St., Woburn, MA 01801 Call ~0.63 miles northeast of Winchester
  • 3-star Suburban property
  • Fitness + Health Center
From£59
Average 3.0 /5 Recent Reviews Call BookMore Details
The Inn At Woburn - Boston - Woburn 14 Hill St., Woburn, MA 01801 Call ~1.96 miles northeast of Winchester
  • Economy Suburban property
  • 65 rooms in hotel
From£44
Very good 4.0 /5 Latest Reviews Call BookMore Details
Best Western Plus New Englander in Woburn 1 Rainin Rd., Woburn, MA 01801 Call ~1.99 miles northeast of Winchester
  • 3-star Suburban property
  • 99 rooms in property
From£53
Average 3.5 /5 Review Score Call BookMore Details
Courtyard by Marriott Woburn/Boston North 700 Unicorn Park Dr., Woburn, MA 01801 Call ~2.44 miles northeast of Winchester
  • Three Star Suburban hotel
  • Gym / Fitness Center Available
From£38
Very good 4.0 /5 Review Score Call BookMore Details
Hilton Boston / Woburn - Woburn 2 Forbes Rd., Woburn, MA 01801 Call ~2.86 miles north of Winchester
  • Midscale Suburban property
  • Check-in: 4:00pm
From£58
Very good 4.0 /5 Guest Reviews Call BookMore Details
Crowne Plaza Boston - Woburn by IHG in Woburn 15 Middlesex Canal Park, Woburn, MA 01801 Call ~2.99 miles north of Winchester
  • Four-star Suburban property
  • Check-in time: 3p
From£78
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Woburn Boston 371a Washington St., Woburn, MA 01801 Call ~3.00 miles north of Winchester
  • Midscale Suburban hotel
  • 132 rooms in hotel
From£96
Average 3.0 /5 Recent Reviews Call BookMore Details
Hyatt Place Boston/Medford 116 Riverside Ave., Medford, MA 02155 Call ~3.11 miles southeast of Winchester
  • Midscale Suburban hotel
  • 2 meeting rooms in hotel
From£66
Very good 4.0 /5 Latest Reviews Call BookMore Details
Fairfield Inn Boston Woburn / Burlington in Woburn 285 Mishawum Rd., Woburn, MA 01801 Call ~3.32 miles north of Winchester
  • Three Star Highway property
  • Complimentary breakfast is offered
From£47
Very good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Boston North Woburn by Ihg 315 Mishawum Rd., Woburn, MA 01801 Call ~3.34 miles north of Winchester
  • 3-star Suburban property
  • 93 rooms in hotel
From£59
Average 3.0 /5 Latest Reviews Call BookMore Details
Sonesta Select Boston Woburn Burlington in Woburn 240 Mishawum Rd., Woburn, MA 01801 Call ~3.35 miles north of Winchester
  • 3 star Suburban hotel
  • 3 floors in hotel
From£47
Very good 4.0 /5 Latest Reviews Call BookMore Details
Extended Stay America Suites Boston Woburn - Woburn 831 Main St., Woburn, MA 01801 Call ~3.49 miles north of Winchester
  • 3 star Suburban property
  • Free breakfast available
From£79
Average 3.0 /5 Recent Reviews Call BookMore Details
Hyatt House Boston Burlington in Burlington 2 Van De Graaff Dr., Burlington, MA 01803 Website Call ~3.50 miles northwest of Winchester
  • Midscale Suburban property
  • 150 rooms in property
From£31
Very good 4.5 /5 Guest Reviews Call BookMore Details
Red Roof Inn PLUS+ Boston - Woburn/ Burlington : 19 Commerce Way 19 Commerce Way, Woburn, MA 01801 Call ~3.54 miles north of Winchester
  • Cheap Suburban property
  • 5 suites in hotel
From£44
Average 3.0 /5 Latest Reviews Call BookMore Details
Homewood Suites by Hilton Boston/Cambridge-Arlington, MA - Arlington 1 Massachusetts Ave., Arlington, MA 02474 Call ~3.69 miles south of Winchester
  • Midscale Suburban property
  • Complimentary breakfast is offered
From£66
Very good 4.0 /5 Read Reviews Call BookMore Details
Boston Marriott Burlington 1 Burlington Mall Rd., Burlington, MA 01803 Call ~3.89 miles northwest of Winchester
  • High end Suburban hotel
  • Hotel has 4 suites
From£88
Very good 4.0 /5 Latest Reviews Call BookMore Details
AC Hotel Boston Cambridge - Cambridge 10 Acorn Park Dr., Cambridge, MA 02140 Website Call ~3.93 miles south of Winchester
  • Midscale Suburban property
  • 150 rooms in property
From£59
Average 3.0 /5 Hotel Reviews Call BookMore Details
Staybridge Suites Boston - Burlington by IHG : 11 Old Concord Rd. 11 Old Concord Rd., Burlington, MA 01803 Call ~4.00 miles west of Winchester
  • 3-star Suburban property
  • Check-in: 3:00 PM
From£56
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Boston Burlington 5 Wheeler Rd., Burlington, MA 01803 Call ~4.04 miles west of Winchester
  • Three Star Suburban hotel
  • 4 floors in property
From£77
Average 3.0 /5 Review Score Call BookMore Details
Residence Inn by Marriott Boston Burlington 400 District Ave., Burlington, MA 01803 Call ~4.24 miles west of Winchester
  • Three Star Suburban property
  • 5 floors in hotel
From£59
Very good 4.0 /5 Recent Reviews Call BookMore Details
Residence Inn by Marriott Boston Woburn 300 Presidential Way, Woburn, MA 01801 Call ~4.50 miles north of Winchester
  • 3-star Suburban property
  • 7 floors in property
From£82
Very good 4.0 /5 Latest Reviews Call BookMore Details
Extended Stay America Suites Boston Burlington : 40 South Ave. 40 South Ave., Burlington, MA 01803 Call ~4.54 miles west of Winchester
  • Low Cost Suburban property
  • 140 rooms in property
From£61
Average 3.0 /5 Guest Reviews Call BookMore Details
Freepoint Hotel Cambridge, Tapestry Collection by Hilton 220 Alewife Brook Pkwy., Cambridge, MA 02138 Call ~4.60 miles south of Winchester
  • 4 star Downtown property
  • Hotel has 2 meeting rooms
From£73
Average 3.0 /5 Latest Reviews Call BookMore Details
Porter Square Hotel in Cambridge 1924 Massachusetts Ave., Cambridge, MA 02140 Call ~4.64 miles south of Winchester
  • 3 star property
  • Check-in: 15:00
From£67
Very good 4.0 /5 Latest Reviews Call BookMore Details
AC Hotel by Marriott Boston North 95 Station Landing, Medford, MA 02155 Call ~4.65 miles southeast of Winchester
  • Three Star Suburban hotel
  • Check in: 3:00PM
From£100
Very good 4.0 /5 Read Reviews Call BookMore Details
Hotel 1868 : 1868 Massachusetts Ave. 1868 Massachusetts Ave., Cambridge, MA 02140 Call ~4.73 miles south of Winchester
  • 3-star property
  • 50 rooms in hotel
From£67
Average 3.0 /5 Guest Reviews Call BookMore Details
Sonesta Simply Suites Boston Burlington : 130 Middlesex Turnpike 130 Middlesex Turnpike, Burlington, MA 01803 Call ~4.77 miles west of Winchester
  • Cheap Suburban hotel
  • Hotel has a green policy Learn more
From£56
Average 3.0 /5 Read Reviews Call BookMore Details
Lakeside Inn - Wakefield 595 North Ave., Wakefield, MA 01880 Call ~4.81 miles northeast of Winchester
  • Two star Suburban property
  • Check in time: 3:00PM
From£39
Average 3.0 /5 Review Score Call BookMore Details
Archer Hotel Boston/Burlington 18 3rd Ave., Burlington, MA 01803 Call ~4.94 miles west of Winchester
  • 4 star Suburban hotel
  • Hotel has 65 suites
From£148
Average 3.0 /5 Guest Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Boston Somerville : 23 Cummings St. 23 Cummings St., Somerville, MA 02145 Call ~4.99 miles southeast of Winchester
  • Three Star Airport hotel
  • Check in: 3:00
From£58
Average 3.0 /5 Latest Reviews Call BookMore Details
The Inn at Hastings Park, Relais & Chateaux - Boston 2027 Massachusetts Ave., Lexington, MA 02421 Call ~5.07 miles west of Winchester
  • Four-star Suburban property
  • 22 rooms in hotel
From£104
Very good 4.0 /5 Recent Reviews Call BookMore Details
Cambria Boston Somerville in Somerville 515 Somerville Ave., Somerville, MA 02143 Website Call ~5.21 miles south of Winchester
  • Mid-scale Suburban hotel
  • 6 floors in hotel
From£59
Average 3.0 /5 Latest Reviews Call BookMore Details
Econo Lodge Boston Malden : 321 Broadway 321 Broadway, Malden, MA 02148 Call ~5.23 miles east of Winchester
  • Two-star Airport property
  • Hotel has 2 floors
From£44
Poor 2.0 /5 Reviews Call BookMore Details
The Row Hotel at Assembly Row, Autograph Collection - Somerville 360 Foley St., Somerville, MA 02145 Call ~5.24 miles southeast of Winchester
  • High end Suburban hotel
  • 5 floors in hotel
From£103
Very good 4.5 /5 Reviews Call BookMore Details
Sheraton Commander Hotel 16 Garden St., Cambridge, MA 02138 Call ~5.32 miles south of Winchester
  • Four star Downtown property
  • Hotel has 6 floors
From£96
Very good 4.0 /5 Reviews Call BookMore Details
Encore Boston Harbor Leg - Everett 1 Broadway, Everett, MA 02149 Call ~5.42 miles southeast of Winchester
  • Affordable property
  • Check-in time: 15:00
From£67
Very good 4.0 /5 Recent Reviews Call BookMore Details
Hotel Malden Ma Bro in Malden 551 Broadway, Malden, MA 2148 Call ~5.47 miles east of Winchester
  • 3-star hotel
  • 21 rooms in hotel
From£67
Average 3.0 /5 Latest Reviews Call BookMore Details
Colonial Traveler Inn 1753 Broadway, Saugus, MA 01906 Call ~5.64 miles east of Winchester
  • Low Cost Highway hotel
  • Hotel has 2 floors
From£44
Average 3.0 /5 Read Reviews Call BookMore Details
Irving House at Harvard in Cambridge 24 Irving St., Cambridge, MA 02138 Call ~5.67 miles south of Winchester
  • 3-star Downtown hotel
  • Check in: 15:00
From£59
Very good 4.0 /5 Reviews Call BookMore Details
Harvard Square Hotel in Cambridge 110 Mount Auburn St., Cambridge, MA 02138 Call ~5.75 miles south of Winchester
  • 2-star Downtown hotel
  • 4 floors in property
From£168
Average 3.0 /5 Guest Reviews Call BookMore Details
The Charles Hotel : 1 Bennett St. 1 Bennett St., Cambridge, MA 02138 Call ~5.78 miles south of Winchester
  • Four-star Downtown hotel
  • 10 floors in property
From£148
Average 3.0 /5 Reviews Call BookMore Details
Quality Inn Boston Revere 100 Morris St., Saugus, MA 01906 Call ~5.80 miles east of Winchester
  • Three Star Highway property
  • Check-in time: 3:00 PM
From£59
Average 3.0 /5 Reviews Call BookMore Details
Quality Inn Boston - Revere in Revere 100 Morris St., Revere, MA 02151 Call ~5.81 miles east of Winchester
  • Mid-scale Highway property
  • Free breakfast available
From£52
Very good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Boston - Saugus by IHG - Saugus 999 Broadway, Saugus, MA 01906 Call ~5.81 miles east of Winchester
  • Two-star Airport property
  • Hotel has an eco-friendly policy Learn more
From£61
Very good 4.0 /5 Read Reviews Call BookMore Details
Quality Inn & Suites Lexington in Lexington 440 Bedford St., Lexington, MA 02420 Call ~5.83 miles west of Winchester
  • 3 star Suburban hotel
  • 198 sleeping rooms in hotel
From£59
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Boston Cambridge Area : 30 Washington St. 30 Washington St., Somerville, MA 02143 Call ~5.83 miles southeast of Winchester
  • Affordable Downtown hotel
  • Check in time: 4:00pm
From£59
Average 3.0 /5 Reviews Call BookMore Details
Envision Hotel Boston Everett Ascend Hotel Collection in Everett 1834 Revere Beach Pkwy., Everett, MA 02149 Call ~5.83 miles southeast of Winchester
  • Midscale Airport property
  • Hotel has 4 floors
From£48
Very good 4.5 /5 Review Score Call BookMore Details
Red Roof Inn PLUS+ Boston - Logan 920 Broadway, Saugus, MA 01906 Call ~5.85 miles east of Winchester
  • Economy Highway property
  • Check in time: 2PM
From£40
Average 3.0 /5 Guest Reviews Call BookMore Details
Extended Stay America Suites - Boston - Saugus : 832 Broadway 832 Broadway, Saugus, MA 01906 Call ~5.87 miles east of Winchester
  • Mid-scale Suburban hotel
  • Check in time: 3:00 PM
From£39
Average 3.0 /5 Hotel Reviews Call BookMore Details

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The Best Time to Visit Winchester, MA

Winchester is known for its mild climate. Due to its location, it often experiences warmer weather than the surrounding communities. In addition, the district is protected from cold winds by the surrounding hills. As a result, Winchester has one of the mildest climates in the state with temperatures varying from 82 °F to 19 °F over the course of the year. Whichever time of year you visit Winchester, MA, there is always something to do. In the spring, the flowers are blooming and the weather is perfect for spending time outdoors. The summer is wonderful for swimming, hiking, and picnicking, while the fall is suitable for taking in the autumn leaves. Winter is a magical time in Winchester, with the snow-covered trees and festive holiday decorations. Whenever you come, Winchester is sure to please.

Hotel Discounts in Winchester, Massachusetts

The availability of special offers for accommodations in Winchester, MA is excellent. There are plenty of offers available for both business and leisure travelers. The prices are very competitive, so it is definitely worth checking the available hotel discounts before booking your stay in Winchester, MA. The town is home to a variety of hotels, all of which provide discounts during different seasons. For example, during the winter months, many hotels offer discounts to guests who book for multiple nights. This is because it is a popular destination for skiers and snowboarders. During the summer months, discounts are often given to guests who book their stay in advance.

Things to do in Winchester, MA

This charming town has something for everyone. Start your day with a stroll down Main Street. You'll find plenty of cute shops and cafes to explore. Be sure to stop in at the Winchester Farmers' Market for some fresh local produce. For a beautiful place to take a hike or a picnic lunch, visit Middlesex Fells Reservation. With 2,571 acres of land, there are plenty of places to explore. The reservation is also home to over 100 species of birds, so it's a great place for bird watching. So come on over to Middlesex Fells Reservation and enjoy the great outdoors. Another great spot to check out is the Griffin Museum of Photography. The museum is a non-profit organization dedicated to celebrating the art of photography. It offers a variety of exhibitions and programs that showcase the work of both emerging and established photographers. Visit this amazing museum and discover the power of photography for yourself.

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