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 Woburn Boston
+1-888-389-4121
371a Washington St., Woburn, MA 01801 +1-888-389-4121 ~0.63 miles northeast of Winchester
  • Affordable Suburban property
  • 6 floors in hotel
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
The Inn At Woburn - Boston in Woburn
+1-888-675-2083
14 Hill St., Woburn, MA 01801 +1-888-675-2083 ~1.97 miles northeast of Winchester
  • Economical Suburban property
  • 65 rooms in property
From$60
Very Good 4.0 /5 Reviews Call BookMore Details
Best Western Plus New Englander - Woburn
+1-800-716-8490
1 Rainin Rd., Woburn, MA 01801 +1-800-716-8490 ~2.00 miles northeast of Winchester
  • Midscale Suburban property
  • Gym / Fitness Center Available
From$72
Average 3.5 /5 Read Reviews Call BookMore Details
Courtyard by Marriott Woburn/Boston North
+1-800-805-5223
700 Unicorn Park Dr., Woburn, MA 01801 +1-800-805-5223 ~2.44 miles northeast of Winchester
  • Mid-scale Suburban property
  • Access to gym on-site
From$51
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Hilton Boston / Woburn
+1-888-965-1860
2 Forbes Rd., Woburn, MA 01801 +1-888-965-1860 ~2.87 miles north of Winchester
  • Midscale Suburban property
  • 344 rooms in property
From$79
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Crowne Plaza Boston - Woburn by IHG : 15 Middlesex Canal Park
+1-888-788-5576
15 Middlesex Canal Park, Woburn, MA 01801 +1-888-788-5576 ~3.00 miles north of Winchester
  • High-end Suburban hotel
  • 12 meeting rooms in hotel
From$105
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hyatt Place Boston/Medford in Medford
+1-888-897-9207
116 Riverside Ave., Medford, MA 02155 +1-888-897-9207 ~3.11 miles southeast of Winchester
  • Affordable Suburban hotel
  • Hotel has 157 rooms
From$89
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Hampton Inn Woburn Boston
+1-888-311-4278
372 Washington St., Woburn, MA 01801 +1-888-311-4278 ~3.11 miles north of Winchester
  • 3 star Suburban property
  • Check-in: 3:00pm
From$119
Average 3.0 /5 Review Score 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
  • 3-star Suburban property
  • 6 floors in property
From$149
Average 3.0 /5 Latest Reviews Call BookMore Details
Fairfield Inn by Marriott Boston Woburn-Burlington - Woburn
+1-888-734-9421
285 Mishawum Rd., Woburn, MA 01801 +1-888-734-9421 ~3.33 miles north of Winchester
  • 3-star Highway property
  • 129 rooms in hotel
From$64
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Boston North-Woburn by IHG in Woburn
+1-888-841-5292
315 Mishawum Rd., Woburn, MA 01801 +1-888-841-5292 ~3.35 miles north of Winchester
  • 3-star Suburban property
  • 5 floors in property
From$80
Average 3.0 /5 Hotel 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
  • Three Star Suburban hotel
  • Check in time: 3:00 PM
From$64
Very Good 4.0 /5 Recent 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 ~3.50 miles north of Winchester
  • Three Star Suburban property
  • Check in time: 03:00 pm
From$107
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hyatt House Boston Burlington - Burlington
+1-888-906-6358
2 Van De Graaff Dr., Burlington, MA 01803 +1-888-906-6358 ~3.51 miles northwest of Winchester
  • Midscale Suburban property
  • Gym / Fitness Center Available
From$42
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Red Roof Inn PLUS+ Boston - Woburn/ Burlington : 19 Commerce Way
+1-888-749-6785
19 Commerce Way, Woburn, MA 01801 +1-888-749-6785 ~3.54 miles north of Winchester
  • Two-star Suburban property
  • 5 floors in property
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Homewood Suites by Hilton Boston / Cambridge / Arlington
+1-888-878-9982
1 Massachusetts Ave., Arlington, MA 02474 Website +1-888-878-9982 ~3.70 miles south of Winchester
  • 3 star Suburban hotel
  • 121 suites in hotel
From$89
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Boston Marriott Burlington
+1-888-389-4485
1 Burlington Mall Rd., Burlington, MA 01803 +1-888-389-4485 ~3.90 miles northwest of Winchester
  • Four star Suburban hotel
  • Hotel has 8 meeting rooms
From$119
Very Good 4.0 /5 Latest Reviews Call BookMore Details
AC Hotel Boston Cambridge : 10 Acorn Park Dr.
+1-888-389-4121
10 Acorn Park Dr., Cambridge, MA 02140 Website +1-888-389-4121 ~3.94 miles south of Winchester
  • Three Star Suburban property
  • 4 floors in property
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Staybridge Suites Boston - Burlington by IHG
+1-888-675-2083
11 Old Concord Rd., Burlington, MA 01803 +1-888-675-2083 ~4.01 miles west of Winchester
  • Mid-scale Suburban hotel
  • Free complimentary breakfast
From$75
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Boston Burlington - Burlington
+1-800-716-8490
5 Wheeler Rd., Burlington, MA 01803 +1-800-716-8490 ~4.05 miles west of Winchester
  • 3 star Suburban property
  • 5 meeting rooms in hotel
From$104
Average 3.0 /5 Hotel Reviews Call BookMore Details
Residence Inn by Marriott Boston Burlington - Burlington
+1-800-805-5223
400 District Ave., Burlington, MA 01803 +1-800-805-5223 ~4.25 miles west of Winchester
  • 3-star Suburban hotel
  • 170 rooms in property
From$80
Very Good 4.0 /5 Read Reviews Call BookMore Details
Residence Inn by Marriott Boston Woburn
+1-888-965-1860
300 Presidential Way, Woburn, MA 01801 +1-888-965-1860 ~4.51 miles north of Winchester
  • 3 star Suburban property
  • Check-in time: 3:00 PM
From$110
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Extended Stay America Suites Boston Burlington - Burlington
+1-888-788-5576
40 South Ave., Burlington, MA 01803 +1-888-788-5576 ~4.55 miles west of Winchester
  • Two star Suburban hotel
  • Complimentary breakfast is offered
From$82
Average 3.0 /5 Read Reviews Call BookMore Details
Freepoint Hotel Cambridge Tapestry Collection by Hilton in Cambridge
+1-888-897-9207
220 Alewife Brook Pkwy., Cambridge, MA 02138 +1-888-897-9207 ~4.61 miles south of Winchester
  • Expensive Downtown property
  • Has environment-friendly policy Learn more
From$99
Average 3.0 /5 Latest 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 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
+1-888-469-4795
95 Station Landing, Medford, MA 02155 +1-888-469-4795 ~4.66 miles southeast of Winchester
  • 3 star Suburban hotel
  • 152 rooms in hotel
From$134
Very Good 4.0 /5 Reviews Call BookMore Details
Hotel 1868 - Cambridge
+1-888-734-9421
1868 Massachusetts Ave., Cambridge, MA 02140 +1-888-734-9421 ~4.74 miles south of Winchester
  • Mid-scale property
  • 50 rooms in property
From$90
Average 3.0 /5 Reviews Call BookMore Details
Sonesta Simply Suites Boston Burlington
+1-888-841-5292
130 Middlesex Turnpike, Burlington, MA 01803 +1-888-841-5292 ~4.78 miles west of Winchester
  • Inexpensive Suburban hotel
  • 149 suites in property
From$75
Average 3.0 /5 Read Reviews Call BookMore Details
Lakeside Inn
+1-888-455-5160
595 North Ave., Wakefield, MA 01880 +1-888-455-5160 ~4.82 miles northeast of Winchester
  • Economical Suburban property
  • 2 floors in property
From$53
Average 3.0 /5 Guest Reviews Call BookMore Details
Archer Hotel Boston/Burlington in Burlington
+1-888-965-8297
18 3rd Ave., Burlington, MA 01803 +1-888-965-8297 ~4.95 miles west of Winchester
  • Four-star Suburban hotel
  • 3 conference rooms in property
From$199
Average 3.0 /5 Review Score Call BookMore Details
La Quinta Inn & Suites by Wyndham Boston Somerville in Somerville
+1-888-906-6358
23 Cummings St., Somerville, MA 02145 +1-888-906-6358 ~5.00 miles southeast of Winchester
  • 3-star property
  • Hotel has 7 floors
From$99
Average 3.0 /5 Reviews Call BookMore Details
The Inn at Hastings Park, Relais & Chateaux - Boston : 2027 Massachusetts Ave.
+1-888-749-6785
2027 Massachusetts Ave., Lexington, MA 02421 +1-888-749-6785 ~5.07 miles west of Winchester
  • 4-star Suburban property
  • Free breakfast available
From$140
Very Good 4.0 /5 Read Reviews Call BookMore Details
Cambria Boston Somerville - Somerville
+1-888-878-9982
515 Somerville Ave., Somerville, MA 02143 Website +1-888-878-9982 ~5.22 miles south of Winchester
  • Affordable Suburban property
  • 19 suites in property
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Econo Lodge Boston Malden
+1-888-389-4485
321 Broadway, Malden, MA 02148 +1-888-389-4485 ~5.24 miles east of Winchester
  • Economy Airport hotel
  • Hotel has 2 floors
The Row Hotel at Assembly Row, Autograph Collection
+1-888-389-4121
360 Foley St., Somerville, MA 02145 +1-888-389-4121 ~5.25 miles southeast of Winchester
  • 4 star Suburban hotel
  • 4 meeting rooms in property
From$139
Very Good 4.5 /5 Latest Reviews Call BookMore Details
Sheraton Commander Hotel
+1-888-675-2083
16 Garden St., Cambridge, MA 02138 +1-888-675-2083 ~5.33 miles south of Winchester
  • High-end Downtown hotel
  • Hotel has 23 suites
From$129
Very Good 4.0 /5 Review Score Call BookMore Details
Encore Boston Harbor Leg - Everett
+1-800-716-8490
1 Broadway, Everett, MA 02149 +1-800-716-8490 ~5.43 miles southeast of Winchester
  • Three Star hotel
  • 567 rooms in property
From$90
Very Good 4.0 /5 Review Score Call BookMore Details
Hotel Malden Ma Bro
+1-800-805-5223
551 Broadway, Malden, MA 2148 +1-800-805-5223 ~5.48 miles east of Winchester
  • Midscale property
  • Check-in time: 15:00
From$90
Average 3.0 /5 Latest Reviews Call BookMore Details
Colonial Traveler Inn in Saugus
+1-888-965-1860
1753 Broadway, Saugus, MA 01906 +1-888-965-1860 ~5.65 miles east of Winchester
  • Two star Highway hotel
  • 24 rooms in property
From$60
Average 3.0 /5 Latest Reviews Call BookMore Details
Irving House at Harvard : 24 Irving St.
+1-888-788-5576
24 Irving St., Cambridge, MA 02138 +1-888-788-5576 ~5.68 miles south of Winchester
  • Three Star Downtown property
  • Hotel has an eco-friendly policy See policy
From$80
Very Good 4.0 /5 Reviews Call BookMore Details
Harvard Square Hotel - Cambridge
+1-888-897-9207
110 Mount Auburn St., Cambridge, MA 02138 +1-888-897-9207 ~5.76 miles south of Winchester
  • Inexpensive Downtown hotel
  • 73 rooms in property
From$225
Average 3.0 /5 Guest Reviews Call BookMore Details
The Charles Hotel : 1 Bennett St.
+1-888-311-4278
1 Bennett St., Cambridge, MA 02138 +1-888-311-4278 ~5.79 miles south of Winchester
  • High end Downtown hotel
  • Fitness + Health Center
From$199
Average 3.0 /5 Hotel Reviews Call BookMore Details
Quality Inn Boston Revere - Saugus
+1-888-469-4795
100 Morris St., Saugus, MA 01906 +1-888-469-4795 ~5.81 miles east of Winchester
  • Affordable Highway hotel
  • 6 suites in property
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Quality Inn Boston - Revere
+1-888-734-9421
100 Morris St., Revere, MA 02151 +1-888-734-9421 ~5.82 miles east of Winchester
  • 3 star Highway property
  • Check-in time: 3:00PM
From$70
Very Good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Express Boston - Saugus by IHG : 999 Broadway
+1-888-841-5292
999 Broadway, Saugus, MA 01906 +1-888-841-5292 ~5.82 miles east of Winchester
  • Low Cost Airport property
  • Hotel has an eco-friendly policy Learn more
From$82
Very Good 4.0 /5 Read Reviews Call BookMore Details
Quality Inn & Suites Lexington - Lexington
+1-888-455-5160
440 Bedford St., Lexington, MA 02420 +1-888-455-5160 ~5.83 miles west of Winchester
  • 3 star Suburban property
  • 198 sleeping rooms in hotel
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Boston Cambridge Area
+1-888-965-8297
30 Washington St., Somerville, MA 02143 +1-888-965-8297 ~5.84 miles southeast of Winchester
  • 3 star Downtown hotel
  • Fitness + Health Center
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
enVision Hotel Boston - Everett, Ascend Hotel Collection
+1-888-906-6358
1834 Revere Beach Pkwy., Everett, MA 02149 +1-888-906-6358 ~5.84 miles southeast of Winchester
  • Mid-scale Airport hotel
  • Hotel has an eco-friendly policy See policy
From$65
Very Good 4.5 /5 Review Score Call BookMore Details
Red Roof Inn Plus+ Boston Logan - Saugus
+1-888-749-6785
920 Broadway, Saugus, MA 01906 +1-888-749-6785 ~5.86 miles east of Winchester
  • Economy Highway property
  • Hotel has 117 rooms
From$54
Average 3.0 /5 Hotel 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
  • 3 star Suburban hotel
  • Access to gym on-site
From$53
Average 3.0 /5 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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