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, Motels & Accommodations

Hampton Inn Boston Woburn
+1-888-389-4121
371a Washington St., Woburn, MA 01801 +1-888-389-4121 ~0.63 miles northeast of Winchester
  • Mid-scale Suburban property
  • 5 floors in hotel
From$75
Very Good 4.0 /5 Review Score Call BookMore Details
Hampton Inn & Homewood Suites by Hilton Boston Woburn in Woburn
+1-888-675-2083
371 Washington St., Woburn, MA 01801 +1-888-675-2083 ~0.63 miles northeast of Winchester
  • Three Star Suburban property
  • Check-in time: 3:00pm
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
The Inn At Woburn - Boston in Woburn
+1-800-716-8490
14 Hill St., Woburn, MA 01801 +1-800-716-8490 ~1.96 miles northeast of Winchester
  • Inexpensive Suburban property
  • 65 rooms in hotel
From$60
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Best Western Plus New Englander - Woburn
+1-800-805-5223
1 Rainin Rd., Woburn, MA 01801 +1-800-805-5223 ~1.99 miles northeast of Winchester
  • Mid-scale Suburban hotel
  • Hotel has 3 meeting rooms
From$72
Average 3.5 /5 Read Reviews Call BookMore Details
Courtyard by Marriott Woburn/Boston North : 700 Unicorn Park Dr.
+1-888-965-1860
700 Unicorn Park Dr., Woburn, MA 01801 +1-888-965-1860 ~2.44 miles northeast of Winchester
  • Midscale Suburban property
  • 6 floors in hotel
From$51
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hilton Boston / Woburn
+1-888-788-5576
2 Forbes Rd., Woburn, MA 01801 +1-888-788-5576 ~2.86 miles north of Winchester
  • Midscale Suburban hotel
  • 15 meeting rooms in property
From$79
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Crowne Plaza Boston - Woburn by IHG
+1-888-897-9207
15 Middlesex Canal Park, Woburn, MA 01801 +1-888-897-9207 ~2.99 miles north of Winchester
  • Four star Suburban hotel
  • Hotel has 4 floors
From$105
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Woburn Boston - Woburn
+1-888-311-4278
371a Washington St., Woburn, MA 01801 +1-888-311-4278 ~3.00 miles north of Winchester
  • Three Star Suburban property
  • 132 sleeping rooms in hotel
From$129
Average 3.0 /5 Recent Reviews Call BookMore Details
Hyatt Place Boston/Medford
+1-888-469-4795
116 Riverside Ave., Medford, MA 02155 +1-888-469-4795 ~3.11 miles southeast of Winchester
  • 3 star Suburban hotel
  • Complimentary breakfast is offered
From$89
Very Good 4.0 /5 Reviews Call BookMore Details
Fairfield Inn by Marriott Boston Woburn-Burlington
+1-888-734-9421
285 Mishawum Rd., Woburn, MA 01801 +1-888-734-9421 ~3.32 miles north of Winchester
  • Three 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
+1-888-841-5292
315 Mishawum Rd., Woburn, MA 01801 +1-888-841-5292 ~3.34 miles north of Winchester
  • Mid-scale Suburban hotel
  • Check-in: 3:00pm
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Sonesta Select Boston Woburn Burlington in Woburn
+1-888-455-5160
240 Mishawum Rd., Woburn, MA 01801 +1-888-455-5160 ~3.35 miles north of Winchester
  • Midscale Suburban property
  • Fitness / Gym is on-site
From$64
Very Good 4.0 /5 Read Reviews Call BookMore Details
Extended Stay America Suites Boston Woburn - Woburn
+1-888-965-8297
831 Main St., Woburn, MA 01801 +1-888-965-8297 ~3.49 miles north of Winchester
  • Midscale Suburban hotel
  • 100 sleeping rooms in hotel
From$107
Average 3.0 /5 Recent Reviews Call BookMore Details
Hyatt House Boston Burlington
+1-888-906-6358
2 Van De Graaff Dr., Burlington, MA 01803 +1-888-906-6358 ~3.50 miles northwest of Winchester
  • 3 star Suburban hotel
  • Free breakfast
From$42
Very Good 4.5 /5 Review Score Call BookMore Details
Red Roof Inn PLUS+ Boston - Woburn/ Burlington
+1-888-749-6785
19 Commerce Way, Woburn, MA 01801 +1-888-749-6785 ~3.54 miles north of Winchester
  • Economical Suburban property
  • 159 rooms in property
From$60
Average 3.0 /5 Guest Reviews Call BookMore Details
Homewood Suites by Hilton Boston / Cambridge / Arlington - Arlington
+1-888-878-9982
1 Massachusetts Ave., Arlington, MA 02474 Website +1-888-878-9982 ~3.69 miles south of Winchester
  • Mid-scale Suburban hotel
  • Fitness center on property
From$89
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Boston Marriott Burlington
+1-888-389-4485
1 Burlington Mall Rd., Burlington, MA 01803 +1-888-389-4485 ~3.89 miles northwest of Winchester
  • Four star Suburban property
  • Fitness + Health Center
From$119
Very Good 4.0 /5 Review Score Call BookMore Details
AC Hotel Boston Cambridge in Cambridge
+1-888-389-4121
10 Acorn Park Dr., Cambridge, MA 02140 Website +1-888-389-4121 ~3.93 miles south of Winchester
  • Affordable Suburban property
  • Check in: 3:00pm
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Staybridge Suites Boston - Burlington by IHG - Burlington
+1-888-675-2083
11 Old Concord Rd., Burlington, MA 01803 +1-888-675-2083 ~4.00 miles west of Winchester
  • 3-star Suburban property
  • 141 sleeping rooms in hotel
From$75
Very Good 4.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Boston Burlington : 5 Wheeler Rd.
+1-800-716-8490
5 Wheeler Rd., Burlington, MA 01803 +1-800-716-8490 ~4.04 miles west of Winchester
  • Three Star Suburban hotel
  • 180 sleeping rooms in hotel
From$104
Average 3.0 /5 Latest Reviews Call BookMore Details
Residence Inn by Marriott Boston Burlington
+1-800-805-5223
400 District Ave., Burlington, MA 01803 +1-800-805-5223 ~4.24 miles west of Winchester
  • Midscale Suburban property
  • Hotel has 2 meeting rooms
From$80
Very Good 4.0 /5 Reviews Call BookMore Details
Residence Inn by Marriott Boston Woburn
+1-888-965-1860
300 Presidential Way, Woburn, MA 01801 +1-888-965-1860 ~4.50 miles north of Winchester
  • Three Star Suburban property
  • Fitness + Health Center
From$110
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Extended Stay America Suites Boston Burlington : 40 South Ave.
+1-888-788-5576
40 South Ave., Burlington, MA 01803 +1-888-788-5576 ~4.54 miles west of Winchester
  • Low priced Suburban hotel
  • Hotel has 3 floors
From$82
Average 3.0 /5 Reviews Call BookMore Details
Freepoint Hotel Cambridge, Tapestry Collection by Hilton : 220 Alewife Brook Pkwy.
+1-888-897-9207
220 Alewife Brook Pkwy., Cambridge, MA 02138 +1-888-897-9207 ~4.60 miles south of Winchester
  • 4-star Downtown hotel
  • 2 meeting rooms in hotel
From$99
Average 3.0 /5 Guest Reviews Call BookMore Details
Porter Square Hotel : 1924 Massachusetts Ave.
+1-888-311-4278
1924 Massachusetts Ave., Cambridge, MA 02140 +1-888-311-4278 ~4.64 miles south of Winchester
  • Affordable property
  • Check-in: 15:00
From$90
Very Good 4.0 /5 Latest Reviews Call BookMore Details
AC Hotel by Marriott Boston North - Medford
+1-888-469-4795
95 Station Landing, Medford, MA 02155 +1-888-469-4795 ~4.65 miles southeast of Winchester
  • Affordable Suburban hotel
  • 152 rooms in property
From$134
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hotel 1868
+1-888-734-9421
1868 Massachusetts Ave., Cambridge, MA 02140 +1-888-734-9421 ~4.73 miles south of Winchester
  • Affordable property
  • Check-in: 15:00
From$90
Average 3.0 /5 Guest Reviews Call BookMore Details
Sonesta Simply Suites Boston Burlington - Burlington
+1-888-841-5292
130 Middlesex Turnpike, Burlington, MA 01803 +1-888-841-5292 ~4.77 miles west of Winchester
  • Two-star Suburban hotel
  • Hotel has 149 rooms
From$75
Average 3.0 /5 Latest Reviews Call BookMore Details
Lakeside Inn in Wakefield
+1-888-455-5160
595 North Ave., Wakefield, MA 01880 +1-888-455-5160 ~4.81 miles northeast of Winchester
  • Two-star Suburban property
  • 89 rooms in hotel
From$53
Average 3.0 /5 Review Score Call BookMore Details
Archer Hotel Boston/Burlington
+1-888-965-8297
18 3rd Ave., Burlington, MA 01803 +1-888-965-8297 ~4.94 miles west of Winchester
  • High-end Suburban property
  • 3 meeting rooms in property
From$199
Average 3.0 /5 Review Score Call BookMore Details
La Quinta Inn & Suites by Wyndham Boston Somerville - Somerville
+1-888-906-6358
23 Cummings St., Somerville, MA 02145 +1-888-906-6358 ~4.99 miles southeast of Winchester
  • Mid-scale Airport property
  • Hotel has 7 floors
From$99
Average 3.0 /5 Recent Reviews Call BookMore Details
The Inn at Hastings Park, Relais & Chateaux - Boston in Lexington
+1-888-749-6785
2027 Massachusetts Ave., Lexington, MA 02421 +1-888-749-6785 ~5.07 miles west of Winchester
  • High end Suburban hotel
  • 7 suites in property
From$140
Very Good 4.0 /5 Read Reviews Call BookMore Details
Cambria Boston Somerville in Somerville
+1-888-878-9982
515 Somerville Ave., Somerville, MA 02143 Website +1-888-878-9982 ~5.21 miles south of Winchester
  • Mid-scale Suburban hotel
  • 6 floors in hotel
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Econo Lodge Boston Malden in Malden
+1-888-389-4485
321 Broadway, Malden, MA 02148 +1-888-389-4485 ~5.23 miles east of Winchester
  • Two star Airport hotel
  • Check-in time: 0200pm
The Row Hotel at Assembly Row, Autograph Collection
+1-888-389-4121
360 Foley St., Somerville, MA 02145 +1-888-389-4121 ~5.24 miles southeast of Winchester
  • Expensive Suburban hotel
  • Hotel has 5 floors
From$139
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Sheraton Commander Hotel
+1-888-675-2083
16 Garden St., Cambridge, MA 02138 +1-888-675-2083 ~5.32 miles south of Winchester
  • 4-star Downtown property
  • 6 floors in hotel
From$129
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Encore Boston Harbor Leg
+1-800-716-8490
1 Broadway, Everett, MA 02149 +1-800-716-8490 ~5.42 miles southeast of Winchester
  • Affordable hotel
  • 567 sleeping rooms in hotel
From$90
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hotel Malden Ma Bro - Malden
+1-800-805-5223
551 Broadway, Malden, MA 2148 +1-800-805-5223 ~5.47 miles east of Winchester
  • 3-star hotel
  • 21 rooms in hotel
From$90
Average 3.0 /5 Latest Reviews Call BookMore Details
Colonial Traveler Inn - Saugus
+1-888-965-1860
1753 Broadway, Saugus, MA 01906 +1-888-965-1860 ~5.64 miles east of Winchester
  • Economy Highway hotel
  • Check in: 3pm
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Irving House at Harvard
+1-888-788-5576
24 Irving St., Cambridge, MA 02138 +1-888-788-5576 ~5.67 miles south of Winchester
  • Midscale Downtown property
  • 44 rooms in property
From$80
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Harvard Square Hotel
+1-888-897-9207
110 Mount Auburn St., Cambridge, MA 02138 +1-888-897-9207 ~5.75 miles south of Winchester
  • Two-star Downtown property
  • 4 floors in hotel
From$225
Average 3.0 /5 Latest Reviews Call BookMore Details
The Charles Hotel : 1 Bennett St.
+1-888-311-4278
1 Bennett St., Cambridge, MA 02138 +1-888-311-4278 ~5.78 miles south of Winchester
  • Expensive Downtown property
  • 303 rooms in property
From$199
Average 3.0 /5 Reviews Call BookMore Details
Quality Inn Boston Revere
+1-888-469-4795
100 Morris St., Saugus, MA 01906 +1-888-469-4795 ~5.80 miles east of Winchester
  • Three Star Highway property
  • Hotel has 5 floors
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Quality Inn Boston - Revere - Revere
+1-888-734-9421
100 Morris St., Revere, MA 02151 +1-888-734-9421 ~5.81 miles east of Winchester
  • 3 star Highway hotel
  • 2 meeting rooms in property
From$70
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Boston - Saugus by IHG - Saugus
+1-888-841-5292
999 Broadway, Saugus, MA 01906 +1-888-841-5292 ~5.81 miles east of Winchester
  • Inexpensive Airport property
  • Hotel has 145 rooms
From$82
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Quality Inn & Suites Lexington in Lexington
+1-888-455-5160
440 Bedford St., Lexington, MA 02420 +1-888-455-5160 ~5.83 miles west of Winchester
  • Three Star Suburban property
  • Hotel has 198 rooms
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Boston Cambridge Area
+1-888-965-8297
30 Washington St., Somerville, MA 02143 +1-888-965-8297 ~5.83 miles southeast of Winchester
  • 3 star Downtown property
  • Hotel has 8 suites
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Envision Hotel Boston Everett Ascend Hotel Collection in Everett
+1-888-906-6358
1834 Revere Beach Pkwy., Everett, MA 02149 +1-888-906-6358 ~5.83 miles southeast of Winchester
  • Three Star Airport hotel
  • 4 floors in property
From$65
Very Good 4.5 /5 Read Reviews Call BookMore Details
Red Roof Inn PLUS+ Boston - Logan : 920 Broadway
+1-888-749-6785
920 Broadway, Saugus, MA 01906 +1-888-749-6785 ~5.85 miles east of Winchester
  • Cheap Highway property
  • 4 suites in hotel
From$54
Average 3.0 /5 Read Reviews Call BookMore Details
Extended Stay America Suites - Boston - Saugus
+1-888-878-9982
832 Broadway, Saugus, MA 01906 +1-888-878-9982 ~5.87 miles east of Winchester
  • Mid-scale Suburban property
  • 4 floors in hotel
From$53
Average 3.0 /5 Latest 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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