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
+1-888-389-4121
371 a Washington St., Woburn, MA 01801 +1-888-389-4121 ~0.63 miles northeast of Winchester
  • 3 star Suburban hotel
  • Check-in: 3:00pm
From£59
Very good 4.0 /5 Read Reviews Call BookMore Details
The Inn At Woburn - Boston
+1-888-675-2083
14 Hill St., Woburn, MA 01801 +1-888-675-2083 ~1.97 miles northeast of Winchester
  • Cheap Suburban hotel
  • Free breakfast
From£47
Very good 4.0 /5 Recent Reviews Call BookMore Details
Best Western Plus New Englander
+1-800-716-8490
1 Rainin Rd., Woburn, MA 01801 +1-800-716-8490 ~2.00 miles northeast of Winchester
  • Midscale Suburban property
  • Hotel has 5 floors
From£57
Average 3.5 /5 Guest Reviews Call BookMore Details
Courtyard by Marriott Woburn/Boston North - Woburn
+1-800-805-5223
700 Unicorn Park Dr., Woburn, MA 01801 +1-800-805-5223 ~2.44 miles northeast of Winchester
  • 3-star Suburban property
  • 11 conference rooms in property
From£40
Very good 4.0 /5 Latest Reviews Call BookMore Details
Hilton Boston / Woburn in Woburn
+1-888-965-1860
2 Forbes Rd., Woburn, MA 01801 +1-888-965-1860 ~2.87 miles north of Winchester
  • 3 star Suburban property
  • Check in: 4:00pm
From£62
Very good 4.0 /5 Recent Reviews Call BookMore Details
Crowne Plaza Boston Woburn An Ihg Hotel - Woburn
+1-888-788-5576
15 Middlesex Canal Park, Woburn, MA 01801 +1-888-788-5576 ~3.00 miles north of Winchester
  • High end Suburban property
  • Check-in time: 3p
From£83
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Hyatt Place Boston/Medford
+1-888-897-9207
116 Riverside Ave., Medford, MA 02155 +1-888-897-9207 ~3.11 miles southeast of Winchester
  • Mid-scale Suburban property
  • Fitness + Health Center
From£70
Very good 4.0 /5 Reviews Call BookMore Details
Hampton Inn Woburn Boston in Woburn
+1-888-311-4278
372 Washington St., Woburn, MA 01801 +1-888-311-4278 ~3.11 miles north of Winchester
  • Midscale Suburban hotel
  • Hotel has 6 floors
From£94
Average 3.0 /5 Reviews Call BookMore Details
Homewood Suites Boston Woburn
+1-888-469-4795
371 Washington St., Woburn, MA 01801 +1-888-469-4795 ~3.13 miles north of Winchester
  • Mid-scale Suburban hotel
  • 6 floors in hotel
From£103
Average 3.0 /5 Latest 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 ~3.33 miles north of Winchester
  • 3-star Highway hotel
  • Comp. Breakfast
From£50
Very good 4.0 /5 Review Score Call BookMore Details
Holiday Inn Express Boston North Woburn An Ihg Hotel
+1-888-841-5292
315 Mishawum Rd., Woburn, MA 01801 +1-888-841-5292 ~3.35 miles north of Winchester
  • Mid-scale Suburban hotel
  • 5 floors in property
From£63
Average 3.0 /5 Guest Reviews Call BookMore Details
Sonesta Select Boston Woburn Burlington - Woburn
+1-888-455-5160
240 Mishawum Rd., Woburn, MA 01801 +1-888-455-5160 ~3.35 miles north of Winchester
  • Midscale Suburban hotel
  • Fitness center on property
From£50
Very good 4.0 /5 Review Score Call BookMore Details
Extended Stay America Suites Boston Woburn - Woburn
+1-888-965-8297
831 Main St., Woburn, MA 01801 +1-888-965-8297 ~3.50 miles north of Winchester
  • Midscale Suburban property
  • Free breakfast available
From£84
Average 3.0 /5 Guest Reviews Call BookMore Details
Hyatt House Boston / Burlington
+1-888-906-6358
2 Van De Graaff Dr., Burlington, MA 01803 +1-888-906-6358 ~3.51 miles northwest of Winchester
  • Mid-scale Suburban hotel
  • 150 rooms in hotel
From£75
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Red Roof Inn PLUS+ Boston - Woburn/ Burlington in Woburn
+1-888-749-6785
19 Commerce Way, Woburn, MA 01801 +1-888-749-6785 ~3.54 miles north of Winchester
  • 2 star Suburban property
  • 159 rooms in hotel
From£47
Average 3.0 /5 Guest Reviews Call BookMore Details
Homewood Suites by Hilton Boston / Cambridge / Arlington
+1-888-878-9982
1 Massachusetts Ave., Arlington, MA 02474 +1-888-878-9982 ~3.70 miles south of Winchester
  • Affordable Suburban property
  • 121 rooms in hotel
From£70
Very good 4.0 /5 Read Reviews Call BookMore Details
AC Hotel by Marriott Boston Cambridge : 10 Acorn Park Dr.
+1-888-389-4485
10 Acorn Park Dr., Cambridge, MA 02140 +1-888-389-4485 ~3.94 miles south of Winchester
  • 4-star Suburban hotel
  • Gym is available on property
From£63
Very good 4.5 /5 Read Reviews Call BookMore Details
Staybridge Suites Burlington Boston, an IHG Hotel
+1-888-389-4121
11 Old Concord Rd., Burlington, MA 01803 +1-888-389-4121 ~4.01 miles west of Winchester
  • Midscale Suburban hotel
  • 141 rooms in property
From£59
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Boston Burlington
+1-888-675-2083
5 Wheeler Rd., Burlington, MA 01803 +1-888-675-2083 ~4.05 miles west of Winchester
  • 3-star Suburban hotel
  • Hotel has 180 rooms
From£82
Average 3.0 /5 Guest Reviews Call BookMore Details
Residence Inn by Marriott Boston Burlington - Burlington
+1-800-716-8490
400 District Ave., Burlington, MA 01803 +1-800-716-8490 ~4.25 miles west of Winchester
  • 3-star Suburban hotel
  • Gym / Fitness Center Available
From£63
Very good 4.0 /5 Guest Reviews Call BookMore Details
Residence Inn by Marriott Boston Woburn - Woburn
+1-800-805-5223
300 Presidential Way, Woburn, MA 01801 +1-800-805-5223 ~4.51 miles north of Winchester
  • Affordable Suburban property
  • 149 sleeping rooms in hotel
From£87
Very good 4.0 /5 Recent Reviews Call BookMore Details
Extended Stay America Suites Boston Burlington
+1-888-965-1860
40 South Ave., Burlington, MA 01803 +1-888-965-1860 ~4.55 miles west of Winchester
  • Cheap Suburban property
  • Hotel has 140 rooms
From£64
Average 3.0 /5 Review Score Call BookMore Details
Freepoint Hotel Cambridge Tapestry Collection by Hilton - Cambridge
+1-888-788-5576
220 Alewife Brook Pkwy., Cambridge, MA 02138 +1-888-788-5576 ~4.61 miles south of Winchester
  • Expensive Downtown property
  • 121 rooms in property
From£78
Average 3.0 /5 Read Reviews Call BookMore Details
Porter Square Hotel in Cambridge
+1-888-897-9207
1924 Massachusetts Ave., Cambridge, MA 02140 +1-888-897-9207 ~4.64 miles south of Winchester
  • Three Star property
  • 9 suites in property
From£71
Very good 4.0 /5 Guest Reviews Call BookMore Details
AC Hotel by Marriott Boston North - Medford
+1-888-311-4278
95 Station Landing, Medford, MA 02155 +1-888-311-4278 ~4.66 miles southeast of Winchester
  • 3-star Suburban property
  • Check-in: 3:00PM
From£106
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Hotel 1868 : 1868 Massachusetts Ave.
+1-888-469-4795
1868 Massachusetts Ave., Cambridge, MA 02140 +1-888-469-4795 ~4.74 miles south of Winchester
  • Three Star hotel
  • Check-in: 15:00
From£71
Average 3.0 /5 Recent Reviews Call BookMore Details
Sonesta Simply Suites Boston Burlington
+1-888-734-9421
130 Middlesex Turnpike, Burlington, MA 01803 +1-888-734-9421 ~4.78 miles west of Winchester
  • 2 star Suburban property
  • Hotel has 149 rooms
From£59
Average 3.0 /5 Guest Reviews Call BookMore Details
Lakeside Inn
+1-888-841-5292
595 North Ave., Wakefield, MA 01880 +1-888-841-5292 ~4.82 miles northeast of Winchester
  • Economy Suburban property
  • 2 meeting rooms in property
From£42
Average 3.0 /5 Hotel Reviews Call BookMore Details
Archer Hotel Boston/Burlington - Burlington
+1-888-455-5160
18 3rd Ave., Burlington, MA 01803 +1-888-455-5160 ~4.95 miles west of Winchester
  • High end Suburban property
  • Hotel has a green policy Read more
From£157
Average 3.0 /5 Recent Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Boston Somerville
+1-888-965-8297
23 Cummings St., Somerville, MA 02145 +1-888-965-8297 ~5.00 miles southeast of Winchester
  • Three Star hotel
  • 147 rooms in hotel
From£78
Average 3.0 /5 Review Score Call BookMore Details
The Inn at Hastings Park, Relais & Chateaux - Boston
+1-888-906-6358
2027 Massachusetts Ave., Lexington, MA 02421 +1-888-906-6358 ~5.07 miles west of Winchester
  • High end Suburban property
  • 3 conference rooms in property
From£110
Very good 4.0 /5 Recent Reviews Call BookMore Details
Cambria Boston Somerville : 515 Somerville Ave.
+1-888-749-6785
515 Somerville Ave., Somerville, MA 02143 Website +1-888-749-6785 ~5.22 miles south of Winchester
  • 3-star Suburban property
  • 19 suites in hotel
From£63
Average 3.0 /5 Review Score Call BookMore Details
Econo Lodge Boston - Malden
+1-888-878-9982
321 Broadway, Malden, MA 02148 +1-888-878-9982 ~5.24 miles east of Winchester
  • Economy Airport hotel
  • 51 sleeping rooms in hotel
From£46
Poor 2.0 /5 Review Score Call BookMore Details
The Row Hotel at Assembly Row, Autograph Collection : 360 Foley St.
+1-888-389-4485
360 Foley St., Somerville, MA 02145 +1-888-389-4485 ~5.25 miles southeast of Winchester
  • 4 star Suburban hotel
  • 7 suites in hotel
From£110
Very good 4.5 /5 Reviews Call BookMore Details
Sheraton Commander Hotel - Cambridge
+1-888-389-4121
16 Garden St., Cambridge, MA 02138 +1-888-389-4121 ~5.33 miles south of Winchester
  • Four star Downtown hotel
  • Hotel has 5 meeting rooms
From£102
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Encore Boston Harbor Leg
+1-888-675-2083
1 Broadway, Everett, MA 02149 +1-888-675-2083 ~5.43 miles southeast of Winchester
  • Three Star hotel
From£71
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Hotel Malden Ma Bro - Malden
+1-800-716-8490
551 Broadway, Malden, MA 2148 +1-800-716-8490 ~5.48 miles east of Winchester
  • Affordable property
  • Check in time: 15:00
From£71
Average 3.0 /5 Reviews Call BookMore Details
Colonial Traveler Inn
+1-800-805-5223
1753 Broadway, Saugus, MA 01906 +1-800-805-5223 ~5.65 miles east of Winchester
  • Inexpensive Highway hotel
  • 24 rooms in property
From£47
Average 3.0 /5 Recent Reviews Call BookMore Details
Irving House at Harvard in Cambridge
+1-888-965-1860
24 Irving St., Cambridge, MA 02138 +1-888-965-1860 ~5.68 miles south of Winchester
  • Midscale Downtown hotel
  • 44 sleeping rooms in hotel
From£63
Very good 4.0 /5 Reviews Call BookMore Details
Harvard Square Hotel - Cambridge
+1-888-788-5576
110 Mount Auburn St., Cambridge, MA 02138 +1-888-788-5576 ~5.76 miles south of Winchester
  • Economical Downtown hotel
  • Hotel has 4 floors
From£178
Average 3.0 /5 Hotel Reviews Call BookMore Details
Quality Inn Boston Revere
+1-888-897-9207
100 Morris St., Saugus, MA 01906 +1-888-897-9207 ~5.81 miles east of Winchester
  • Affordable Highway hotel
  • Gym / Fitness Center Available
From£63
Average 3.0 /5 Guest Reviews Call BookMore Details
Quality Inn Boston - Revere : 100 Morris St.
+1-888-311-4278
100 Morris St., Revere, MA 02151 +1-888-311-4278 ~5.82 miles east of Winchester
  • Affordable Highway hotel
  • Hotel has 2 meeting rooms
From£55
Very good 4.0 /5 Review Score Call BookMore Details
Holiday Inn Express Boston - Saugus in Saugus
+1-888-469-4795
999 Broadway, Saugus, MA 01906 +1-888-469-4795 ~5.82 miles east of Winchester
  • Low Cost Airport property
  • Hotel has 145 rooms
From£64
Very good 4.0 /5 Read Reviews Call BookMore Details
Quality Inn & Suites Lexington
+1-888-734-9421
440 Bedford St., Lexington, MA 02420 +1-888-734-9421 ~5.83 miles west of Winchester
  • Midscale Suburban property
  • 198 rooms in property
From£63
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Boston Bunker Hill in Somerville
+1-888-841-5292
30 Washington St., Somerville, MA 02143 +1-888-841-5292 ~5.84 miles southeast of Winchester
  • 3 star Downtown hotel
  • Hotel has 8 suites
From£63
Average 3.0 /5 Review Score Call BookMore Details
enVision Hotel Boston - Everett, Ascend Hotel Collection - Everett
+1-888-455-5160
1834 Revere Beach Pkwy., Everett, MA 02149 +1-888-455-5160 ~5.84 miles southeast of Winchester
  • Affordable Airport property
  • Check in time: 3:00 PM
From£51
Very good 4.5 /5 Hotel Reviews Call BookMore Details
Red Roof Inn PLUS+ Boston - Logan - Saugus
+1-888-965-8297
920 Broadway, Saugus, MA 01906 +1-888-965-8297 ~5.86 miles east of Winchester
  • Two star Highway hotel
  • 3 floors in property
From£42
Average 3.0 /5 Hotel Reviews Call BookMore Details
Extended Stay America Suites - Boston - Saugus : 832 Broadway
+1-888-906-6358
832 Broadway, Saugus, MA 01906 +1-888-906-6358 ~5.87 miles east of Winchester
  • Mid-scale Suburban hotel
  • Hotel has 126 rooms
From£42
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hotel Veritas in Cambridge
+1-888-749-6785
1 Remington St., Cambridge, MA 02138 +1-888-749-6785 ~5.96 miles south of Winchester
  • High end Downtown hotel
  • Gym / Fitness Center Available
From£118
Very good 4.0 /5 Hotel Reviews Call BookMore Details
DoubleTree by Hilton Hotel Boston - Bedford Glen : 44 Middlesex Turnpike
+1-888-878-9982
44 Middlesex Turnpike, Bedford, MA 01730 +1-888-878-9982 ~6.27 miles northwest of Winchester
  • 3 star Suburban hotel
  • Hotel has 15 suites
From£70
Very good 4.0 /5 Recent 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