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 in Woburn 371a Washington St., Woburn, MA 01801 Call ~0.63 miles northeast of Winchester
  • Affordable Suburban hotel
  • 132 rooms in hotel
From$75
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hampton Inn & Homewood Suites by Hilton Boston Woburn : 371 Washington St. 371 Washington St., Woburn, MA 01801 Call ~0.63 miles northeast of Winchester
  • Mid-scale Suburban hotel
  • Hotel has 132 rooms
From$80
Average 3.0 /5 Reviews Call BookMore Details
The Inn At Woburn - Boston : 14 Hill St. 14 Hill St., Woburn, MA 01801 Call ~1.96 miles northeast of Winchester
  • Low Cost Suburban hotel
  • Free breakfast available
From$60
Very Good 4.0 /5 Review Score Call BookMore Details
Best Western Plus New Englander 1 Rainin Rd., Woburn, MA 01801 Call ~1.99 miles northeast of Winchester
  • Three Star Suburban property
  • Fitness + Health Center
From$72
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
  • Midscale Suburban property
  • Hotel has 6 floors
From$51
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hilton Boston / Woburn 2 Forbes Rd., Woburn, MA 01801 Call ~2.86 miles north of Winchester
  • Three Star Suburban hotel
  • Check in: 4:00pm
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 Call ~2.99 miles north of Winchester
  • 4 star Suburban property
  • Check in: 3p
From$105
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Woburn Boston in Woburn 371a Washington St., Woburn, MA 01801 Call ~3.00 miles north of Winchester
  • Mid-scale Suburban property
  • Check-in: 3:00pm
From$129
Average 3.0 /5 Guest Reviews Call BookMore Details
Hyatt Place Boston/Medford 116 Riverside Ave., Medford, MA 02155 Call ~3.11 miles southeast of Winchester
  • Affordable Suburban property
  • Fitness center on property
From$89
Very Good 4.0 /5 Reviews Call BookMore Details
Fairfield Inn Boston Woburn / Burlington - Woburn 285 Mishawum Rd., Woburn, MA 01801 Call ~3.32 miles north of Winchester
  • 3 star Highway property
  • Check-in: 3:00 PM
From$64
Very Good 4.0 /5 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
  • Three Star Suburban property
  • Gym is available on property
From$80
Average 3.0 /5 Review Score Call BookMore Details
Sonesta Select Boston Woburn Burlington 240 Mishawum Rd., Woburn, MA 01801 Call ~3.35 miles north of Winchester
  • 3 star Suburban hotel
  • Check in: 3:00 PM
From$64
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Extended Stay America Suites Boston Woburn in Woburn 831 Main St., Woburn, MA 01801 Call ~3.49 miles north of Winchester
  • Midscale Suburban property
  • Comp. Breakfast
From$107
Average 3.0 /5 Reviews Call BookMore Details
Hyatt House Boston Burlington 2 Van De Graaff Dr., Burlington, MA 01803 Website Call ~3.50 miles northwest of Winchester
  • Three Star Suburban hotel
  • Gym / Fitness Center Available
From$42
Very Good 4.5 /5 Review Score Call BookMore Details
Red Roof Inn PLUS+ Boston - Woburn/ Burlington - Woburn 19 Commerce Way, Woburn, MA 01801 Call ~3.54 miles north of Winchester
  • Two-star Suburban hotel
  • Hotel has 5 floors
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Homewood Suites by Hilton Boston/Cambridge-Arlington, MA 1 Massachusetts Ave., Arlington, MA 02474 Call ~3.69 miles south of Winchester
  • 3 star Suburban hotel
  • Hotel has 121 suites
From$89
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Boston Marriott Burlington 1 Burlington Mall Rd., Burlington, MA 01803 Call ~3.89 miles northwest of Winchester
  • Four star Suburban hotel
  • Check-in: 3:00 PM
From$119
Very Good 4.0 /5 Reviews Call BookMore Details
AC Hotel Boston Cambridge 10 Acorn Park Dr., Cambridge, MA 02140 Website Call ~3.93 miles south of Winchester
  • Affordable Suburban property
  • Access to gym on-site
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Staybridge Suites Boston - Burlington by IHG in Burlington 11 Old Concord Rd., Burlington, MA 01803 Call ~4.00 miles west of Winchester
  • Mid-scale Suburban property
  • Hotel has 141 suites
From$75
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Hilton Garden Inn Boston Burlington 5 Wheeler Rd., Burlington, MA 01803 Call ~4.04 miles west of Winchester
  • Mid-scale Suburban hotel
  • Gym / Fitness Center Available
From$104
Average 3.0 /5 Read Reviews Call BookMore Details
Residence Inn by Marriott Boston Burlington : 400 District Ave. 400 District Ave., Burlington, MA 01803 Call ~4.24 miles west of Winchester
  • Affordable Suburban property
  • 5 floors in hotel
From$80
Very Good 4.0 /5 Review Score Call BookMore Details
Residence Inn by Marriott Boston Woburn - Woburn 300 Presidential Way, Woburn, MA 01801 Call ~4.50 miles north of Winchester
  • Three Star Suburban property
  • Hotel has 149 rooms
From$110
Very Good 4.0 /5 Recent 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
  • Economy Suburban hotel
  • Complimentary breakfast is offered
From$82
Average 3.0 /5 Hotel Reviews Call BookMore Details
Freepoint Hotel Cambridge, Tapestry Collection by Hilton in Cambridge 220 Alewife Brook Pkwy., Cambridge, MA 02138 Call ~4.60 miles south of Winchester
  • Expensive Downtown property
  • Check in: 3:00 PM
From$99
Average 3.0 /5 Recent Reviews Call BookMore Details
Porter Square Hotel 1924 Massachusetts Ave., Cambridge, MA 02140 Call ~4.64 miles south of Winchester
  • Mid-scale hotel
  • Check-in time: 15:00
From$90
Very Good 4.0 /5 Recent Reviews Call BookMore Details
AC Hotel by Marriott Boston North in Medford 95 Station Landing, Medford, MA 02155 Call ~4.65 miles southeast of Winchester
  • Midscale Suburban property
  • Hotel has 3 meeting rooms
From$134
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Hotel 1868 : 1868 Massachusetts Ave. 1868 Massachusetts Ave., Cambridge, MA 02140 Call ~4.73 miles south of Winchester
  • Affordable property
  • 50 sleeping rooms in hotel
From$90
Average 3.0 /5 Guest Reviews Call BookMore Details
Sonesta Simply Suites Boston Burlington 130 Middlesex Turnpike, Burlington, MA 01803 Call ~4.77 miles west of Winchester
  • Economy Suburban property
  • 149 rooms in hotel
From$75
Average 3.0 /5 Guest Reviews Call BookMore Details
Lakeside Inn 595 North Ave., Wakefield, MA 01880 Call ~4.81 miles northeast of Winchester
  • Low priced Suburban hotel
  • 89 suites in hotel
From$53
Average 3.0 /5 Reviews Call BookMore Details
Archer Hotel Boston/Burlington : 18 3rd Ave. 18 3rd Ave., Burlington, MA 01803 Call ~4.94 miles west of Winchester
  • Expensive Suburban property
  • Hotel has an eco-friendly policy See more
From$199
Average 3.0 /5 Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Boston Somerville 23 Cummings St., Somerville, MA 02145 Call ~4.99 miles southeast of Winchester
  • Affordable Airport hotel
  • 7 floors in hotel
From$79
Average 3.0 /5 Review Score Call BookMore Details
The Inn at Hastings Park, Relais & Chateaux - Boston : 2027 Massachusetts Ave. 2027 Massachusetts Ave., Lexington, MA 02421 Call ~5.07 miles west of Winchester
  • Four star Suburban hotel
  • Check-in time: 4:00PM
From$140
Very Good 4.0 /5 Reviews Call BookMore Details
Cambria Boston Somerville - Somerville 515 Somerville Ave., Somerville, MA 02143 Website Call ~5.21 miles south of Winchester
  • Midscale Suburban hotel
  • Check-in: 3:00 PM
From$80
Average 3.0 /5 Review Score Call BookMore Details
Econo Lodge Boston Malden : 321 Broadway 321 Broadway, Malden, MA 02148 Call ~5.23 miles east of Winchester
  • Two-star Airport hotel
  • 51 rooms in hotel
The Row Hotel at Assembly Row, Autograph Collection in Somerville 360 Foley St., Somerville, MA 02145 Call ~5.24 miles southeast of Winchester
  • 4 star Suburban property
  • 5 floors in property
From$139
Very Good 4.5 /5 Reviews Call BookMore Details
Sheraton Commander Hotel in Cambridge 16 Garden St., Cambridge, MA 02138 Call ~5.32 miles south of Winchester
  • High end Downtown property
  • 175 rooms in property
From$129
Very Good 4.0 /5 Reviews Call BookMore Details
Encore Boston Harbor Leg : 1 Broadway 1 Broadway, Everett, MA 02149 Call ~5.42 miles southeast of Winchester
  • Affordable hotel
  • Hotel has 567 rooms
From$90
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hotel Malden Ma Bro : 551 Broadway 551 Broadway, Malden, MA 2148 Call ~5.47 miles east of Winchester
  • Three Star hotel
  • 21 rooms in hotel
From$90
Average 3.0 /5 Guest Reviews Call BookMore Details
Colonial Traveler Inn 1753 Broadway, Saugus, MA 01906 Call ~5.64 miles east of Winchester
  • Economy Highway property
  • Check-in: 3pm
From$60
Average 3.0 /5 Hotel Reviews Call BookMore Details
Irving House at Harvard 24 Irving St., Cambridge, MA 02138 Call ~5.67 miles south of Winchester
  • Midscale Downtown hotel
  • Hotel has an eco-friendly policy Learn more
From$80
Very Good 4.0 /5 Reviews Call BookMore Details
Harvard Square Hotel - Cambridge 110 Mount Auburn St., Cambridge, MA 02138 Call ~5.75 miles south of Winchester
  • Economical Downtown property
  • 4 floors in hotel
From$225
Average 3.0 /5 Guest Reviews Call BookMore Details
The Charles Hotel 1 Bennett St., Cambridge, MA 02138 Call ~5.78 miles south of Winchester
  • High-end Downtown hotel
  • 45 suites in property
From$199
Average 3.0 /5 Guest Reviews Call BookMore Details
Quality Inn Boston Revere - Saugus 100 Morris St., Saugus, MA 01906 Call ~5.80 miles east of Winchester
  • 3 star Highway property
  • Hotel has 154 rooms
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Quality Inn Boston - Revere 100 Morris St., Revere, MA 02151 Call ~5.81 miles east of Winchester
  • Affordable Highway property
  • Comp. Breakfast
From$70
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Boston - Saugus by IHG in Saugus 999 Broadway, Saugus, MA 01906 Call ~5.81 miles east of Winchester
  • Cheap Airport property
  • Check in time: 3:00 PM
From$82
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Quality Inn & Suites Lexington 440 Bedford St., Lexington, MA 02420 Call ~5.83 miles west of Winchester
  • Affordable Suburban hotel
  • 198 sleeping rooms in hotel
From$80
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Boston Cambridge Area 30 Washington St., Somerville, MA 02143 Call ~5.83 miles southeast of Winchester
  • Midscale Downtown property
  • Hotel has a green policy See policy
From$80
Average 3.0 /5 Review Score Call BookMore Details
Envision Hotel Boston Everett Ascend Hotel Collection : 1834 Revere Beach Pkwy. 1834 Revere Beach Pkwy., Everett, MA 02149 Call ~5.83 miles southeast of Winchester
  • Three Star Airport hotel
  • Check-in time: 3:00 PM
From$65
Very Good 4.5 /5 Read Reviews Call BookMore Details
Red Roof Inn PLUS+ Boston - Logan - Saugus 920 Broadway, Saugus, MA 01906 Call ~5.85 miles east of Winchester
  • Cheap Highway hotel
  • 3 floors in hotel
From$54
Average 3.0 /5 Hotel Reviews Call BookMore Details
Extended Stay America Suites - Boston - Saugus in Saugus 832 Broadway, Saugus, MA 01906 Call ~5.87 miles east of Winchester
  • Affordable Suburban property
  • Check-in: 3:00 PM
From$53
Average 3.0 /5 Read Reviews Call BookMore Details

Next: See My Winchester Hotels with Pricing

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.

Back to Top