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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
371 a Washington St., Woburn, MA 01801 ~0.63 miles northeast of Winchester
  • Affordable Suburban property
  • Check in time: 3:00pm
From£59
Very good 4.0 /5 Reviews Call BookMore Details
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The Inn At Woburn - Boston - Woburn
+1-888-675-2083
14 Hill St., Woburn, MA 01801 ~1.97 miles northeast of Winchester
  • Economy Suburban hotel
  • Access to gym on-site
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 ~2.00 miles northeast of Winchester
  • 3-star Suburban hotel
  • Comp. Breakfast
From£57
Average 3.5 /5 Recent Reviews Call BookMore Details
Courtyard by Marriott Woburn/Boston North
+1-800-805-5223
700 Unicorn Park Dr., Woburn, MA 01801 ~2.44 miles northeast of Winchester
  • Affordable Suburban hotel
  • 192 rooms in hotel
From£40
Very good 4.0 /5 Review Score Call BookMore Details
Hilton Boston / Woburn : 2 Forbes Rd.
+1-888-965-1860
2 Forbes Rd., Woburn, MA 01801 ~2.87 miles north of Winchester
  • Mid-scale Suburban hotel
  • 344 rooms in property
From£62
Very good 4.0 /5 Guest Reviews Call BookMore Details
Crowne Plaza Boston Woburn An Ihg Hotel
+1-888-788-5576
15 Middlesex Canal Park, Woburn, MA 01801 ~3.00 miles north of Winchester
  • Expensive Suburban hotel
  • Hotel has 4 floors
From£83
Very good 4.0 /5 Guest Reviews Call BookMore Details
Hyatt Place Boston/Medford
+1-888-897-9207
116 Riverside Ave., Medford, MA 02155 ~3.11 miles southeast of Winchester
  • 3 star Suburban property
  • Hotel has 8 floors
From£70
Very good 4.0 /5 Recent Reviews Call BookMore Details
Hampton Inn Woburn Boston
+1-888-311-4278
372 Washington St., Woburn, MA 01801 ~3.11 miles north of Winchester
  • Mid-scale Suburban property
  • Fitness / Gym is on-site
From£94
Average 3.0 /5 Review Score Call BookMore Details
Homewood Suites Boston Woburn - Woburn
+1-888-469-4795
371 Washington St., Woburn, MA 01801 ~3.13 miles north of Winchester
  • 3 star Suburban property
  • 6 floors in property
From£103
Average 3.0 /5 Recent Reviews Call BookMore Details
Fairfield Inn by Marriott Boston Woburn-Burlington
+1-888-734-9421
285 Mishawum Rd., Woburn, MA 01801 ~3.33 miles north of Winchester
  • 3-star Highway property
  • Hotel has 6 floors
From£50
Very good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Express Boston North Woburn An Ihg Hotel
+1-888-841-5292
315 Mishawum Rd., Woburn, MA 01801 ~3.35 miles north of Winchester
  • Three Star Suburban property
  • 5 floors in property
From£63
Average 3.0 /5 Guest Reviews Call BookMore Details
Sonesta Select Boston Woburn Burlington
+1-888-455-5160
240 Mishawum Rd., Woburn, MA 01801 ~3.35 miles north of Winchester
  • Affordable Suburban property
  • Hotel has 2 meeting rooms
From£50
Very good 4.0 /5 Read Reviews Call BookMore Details
Extended Stay America Suites Boston Woburn in Woburn
+1-888-965-8297
831 Main St., Woburn, MA 01801 ~3.50 miles north of Winchester
  • Mid-scale Suburban hotel
  • Comp. Breakfast
From£85
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 ~3.51 miles northwest of Winchester
  • 3 star Suburban hotel
  • Free comp. breakfast
From£75
Very good 4.0 /5 Recent Reviews Call BookMore Details
Red Roof Inn PLUS+ Boston - Woburn/ Burlington - Woburn
+1-888-749-6785
19 Commerce Way, Woburn, MA 01801 ~3.54 miles north of Winchester
  • Inexpensive Suburban property
  • 159 rooms in property
From£47
Average 3.0 /5 Recent Reviews Call BookMore Details
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Homewood Suites by Hilton Boston / Cambridge / Arlington : 1 Massachusetts Ave.
+1-888-878-9982
1 Massachusetts Ave., Arlington, MA 02474 ~3.70 miles south of Winchester
  • Affordable Suburban hotel
  • 3 floors in hotel
From£70
Very good 4.0 /5 Review Score Call BookMore Details
AC Hotel by Marriott Boston Cambridge
+1-888-389-4485
10 Acorn Park Dr., Cambridge, MA 02140 ~3.94 miles south of Winchester
  • High-end Suburban property
  • 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 ~4.01 miles west of Winchester
  • 3 star Suburban hotel
  • Check-in: 3:00 PM
From£59
Very good 4.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Boston Burlington in Burlington
+1-888-675-2083
5 Wheeler Rd., Burlington, MA 01803 ~4.05 miles west of Winchester
  • 3-star Suburban property
  • 5 conference rooms in property
From£82
Average 3.0 /5 Guest Reviews Call BookMore Details
Residence Inn by Marriott Boston Burlington
+1-800-716-8490
400 District Ave., Burlington, MA 01803 ~4.25 miles west of Winchester
  • Affordable Suburban hotel
  • Hotel has 170 rooms
From£63
Very good 4.0 /5 Latest Reviews Call BookMore Details
Residence Inn by Marriott Boston Woburn - Woburn
+1-800-805-5223
300 Presidential Way, Woburn, MA 01801 ~4.51 miles north of Winchester
  • 3 star Suburban hotel
  • 7 floors in hotel
From£87
Very good 4.0 /5 Latest Reviews Call BookMore Details
Extended Stay America Suites Boston Burlington in Burlington
+1-888-965-1860
40 South Ave., Burlington, MA 01803 ~4.55 miles west of Winchester
  • 2-star Suburban property
  • Check in: 1500
From£65
Average 3.0 /5 Read Reviews Call BookMore Details
Freepoint Hotel Cambridge Tapestry Collection by Hilton in Cambridge
+1-888-788-5576
220 Alewife Brook Pkwy., Cambridge, MA 02138 ~4.61 miles south of Winchester
  • 4 star Downtown hotel
  • Fitness + Health Center
From£78
Average 3.0 /5 Reviews Call BookMore Details
Porter Square Hotel - Cambridge
+1-888-897-9207
1924 Massachusetts Ave., Cambridge, MA 02140 ~4.64 miles south of Winchester
  • 3-star hotel
  • 9 suites in hotel
From£71
Very good 4.0 /5 Recent Reviews Call BookMore Details
AC Hotel by Marriott Boston North : 95 Station Landing
+1-888-311-4278
95 Station Landing, Medford, MA 02155 ~4.66 miles southeast of Winchester
  • Affordable Suburban hotel
  • 3 conference rooms in property
From£106
Very good 4.0 /5 Reviews Call BookMore Details
Hotel 1868 - Cambridge
+1-888-469-4795
1868 Massachusetts Ave., Cambridge, MA 02140 ~4.74 miles south of Winchester
  • Midscale hotel
  • Hotel has 50 rooms
From£71
Average 3.0 /5 Guest Reviews Call BookMore Details
Sonesta Simply Suites Boston Burlington - Burlington
+1-888-734-9421
130 Middlesex Turnpike, Burlington, MA 01803 ~4.78 miles west of Winchester
  • Economy Suburban hotel
  • Fitness + Health Center
From£59
Average 3.0 /5 Reviews Call BookMore Details
Lakeside Inn
+1-888-841-5292
595 North Ave., Wakefield, MA 01880 ~4.82 miles northeast of Winchester
  • Cheap Suburban property
  • 89 sleeping rooms in hotel
From£42
Average 3.0 /5 Reviews Call BookMore Details
Archer Hotel Boston/Burlington - Burlington
+1-888-455-5160
18 3rd Ave., Burlington, MA 01803 ~4.95 miles west of Winchester
  • 4-star Suburban hotel
  • Hotel has 3 meeting rooms
From£158
Average 3.0 /5 Read Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Boston Somerville
+1-888-965-8297
23 Cummings St., Somerville, MA 02145 ~5.00 miles southeast of Winchester
  • 3-star hotel
  • Hotel has 147 rooms
From£78
Average 3.0 /5 Hotel Reviews Call BookMore Details
The Inn at Hastings Park, Relais & Chateaux - Boston in Lexington
+1-888-906-6358
2027 Massachusetts Ave., Lexington, MA 02421 ~5.07 miles west of Winchester
  • High end Suburban hotel
  • 22 sleeping rooms in hotel
From£111
Very good 4.0 /5 Recent Reviews Call BookMore Details
Cambria Boston Somerville
+1-888-749-6785
515 Somerville Ave., Somerville, MA 02143 Website ~5.22 miles south of Winchester
  • Three Star Suburban hotel
  • 6 floors in hotel
From£63
Average 3.0 /5 Latest Reviews Call BookMore Details
Econo Lodge Boston - Malden
+1-888-878-9982
321 Broadway, Malden, MA 02148 ~5.24 miles east of Winchester
  • Two-star Airport hotel
  • 2 floors in property
The Row Hotel at Assembly Row, Autograph Collection in Somerville
+1-888-389-4485
360 Foley St., Somerville, MA 02145 ~5.25 miles southeast of Winchester
  • High-end Suburban hotel
  • Hotel has 5 floors
From£110
Very good 4.5 /5 Review Score Call BookMore Details
Sheraton Commander Hotel
+1-888-389-4121
16 Garden St., Cambridge, MA 02138 ~5.33 miles south of Winchester
  • High-end Downtown property
  • 5 meeting rooms in hotel
From£102
Very good 4.0 /5 Recent Reviews Call BookMore Details
Encore Boston Harbor Leg in Everett
+1-888-675-2083
1 Broadway, Everett, MA 02149 ~5.43 miles southeast of Winchester
  • 3-star property
From£71
Very good 4.0 /5 Reviews Call BookMore Details
Hotel Malden Ma Bro - Malden
+1-800-716-8490
551 Broadway, Malden, MA 2148 ~5.48 miles east of Winchester
  • 3 star property
  • Check-in time: 15:00
From£71
Average 3.0 /5 Latest Reviews Call BookMore Details
Colonial Traveler Inn : 1753 Broadway
+1-800-805-5223
1753 Broadway, Saugus, MA 01906 ~5.65 miles east of Winchester
  • Two-star Highway property
  • Check in: 3pm
From£47
Average 3.0 /5 Review Score Call BookMore Details
Irving House at Harvard : 24 Irving St.
+1-888-965-1860
24 Irving St., Cambridge, MA 02138 ~5.68 miles south of Winchester
  • Midscale Downtown property
  • Hotel has 4 floors
From£63
Very good 4.0 /5 Recent Reviews Call BookMore Details
Harvard Square Hotel
+1-888-788-5576
110 Mount Auburn St., Cambridge, MA 02138 ~5.76 miles south of Winchester
  • Low priced Downtown property
  • 73 sleeping rooms in hotel
From£178
Average 3.0 /5 Recent Reviews Call BookMore Details
Quality Inn Boston Revere - Saugus
+1-888-897-9207
100 Morris St., Saugus, MA 01906 ~5.81 miles east of Winchester
  • Three Star Highway property
  • Gym is available on property
From£63
Average 3.0 /5 Recent Reviews Call BookMore Details
Quality Inn Boston - Revere
+1-888-311-4278
100 Morris St., Revere, MA 02151 ~5.82 miles east of Winchester
  • Mid-scale Highway property
  • 2 meeting rooms in hotel
From£55
Very good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express Boston - Saugus
+1-888-469-4795
999 Broadway, Saugus, MA 01906 ~5.82 miles east of Winchester
  • Cheap Airport property
  • Hotel has 4 floors
From£65
Very good 4.0 /5 Review Score Call BookMore Details
Quality Inn & Suites Lexington in Lexington
+1-888-734-9421
440 Bedford St., Lexington, MA 02420 ~5.83 miles west of Winchester
  • Three Star Suburban property
  • 198 sleeping rooms in hotel
From£63
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Boston Cambridge Area in Somerville
+1-888-841-5292
30 Washington St., Somerville, MA 02143 ~5.84 miles southeast of Winchester
  • 3-star Downtown property
  • Hotel has 9 floors
From£63
Average 3.0 /5 Reviews Call BookMore Details
enVision Hotel Boston - Everett, Ascend Hotel Collection - Everett
+1-888-455-5160
1834 Revere Beach Pkwy., Everett, MA 02149 ~5.84 miles southeast of Winchester
  • 3 star Airport hotel
  • Hotel has an eco-friendly policy See more
From£51
Very good 4.5 /5 Review Score Call BookMore Details
Red Roof Inn PLUS+ Boston - Logan
+1-888-965-8297
920 Broadway, Saugus, MA 01906 ~5.86 miles east of Winchester
  • 2-star Highway property
  • Hotel has 117 rooms
From£42
Average 3.0 /5 Read Reviews Call BookMore Details
Extended Stay America Suites - Boston - Saugus
+1-888-906-6358
832 Broadway, Saugus, MA 01906 ~5.87 miles east of Winchester
  • Midscale Suburban hotel
  • Check in time: 3:00 PM
From£42
Average 3.0 /5 Review Score Call BookMore Details
Hotel Veritas - Cambridge
+1-888-749-6785
1 Remington St., Cambridge, MA 02138 ~5.96 miles south of Winchester
  • High end Downtown property
  • Gym / Fitness Center Available
From£118
Very good 4.0 /5 Guest Reviews Call BookMore Details
DoubleTree by Hilton Hotel Boston - Bedford Glen
+1-888-878-9982
44 Middlesex Turnpike, Bedford, MA 01730 ~6.27 miles northwest of Winchester
  • Mid-scale Suburban hotel
  • Hotel has 16 meeting rooms
From£70
Very good 4.0 /5 Guest Reviews Call BookMore Details

Next: See My Winchester Hotels with Pricing

Graph: Upcoming 20 Days of Winchester Hotel Rates

Rates shown are nightly rates before taxes and do not necessarily reflect all Winchester, MA discounts available. The chart reflects the cheapest Winchester hotel for each day and each star rating category.

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.

Below is a chart of the current pricing seasonality of hotels and motels in Winchester, MA:

Averate Rates by Star Rating

Below we've posted 3 graphs displaying average nightly cost patterns by star rating class in Winchester, MA. Analyze these charts to calculate the best time to book in Winchester during the year.

Premium and Luxury Hotel Options in Winchester, MA

4 Star Average Prices: £144.53

For a truly luxurious stay in Winchester, MA, look no further than the local premium accommodations. There are many premium accommodations available in Winchester, Massachusetts. There are several hotels, that offer luxurious accommodations and amenities. There are also several bed and breakfast inns that offer a more intimate and personal experience. Whatever your preference, you are sure to find the perfect place to stay in Winchester. Their spacious rooms and suites can comfortably accommodate groups of all sizes, and their convenient locations near all the best attractions in Winchester make them the best choice for you. Whether you're in town for business or pleasure, you will be able to find a premium-class suite that is perfect for your taste. And with friendly staff always on hand, your every need will be taken care of. So book a room in one of the local luxury hotels today and start planning your amazing trip to Winchester.

Cheap Lodgings in Winchester, Massachusetts

3 Star Average Prices: £118.20

As a popular destination for visitors, Winchester offers a number of affordable lodgings available in and around the town. There are a number of cheaper accommodations available in Winchester, Massachusetts. These include a number of hotels, motels, and inns. Many of these establishments are located near the city center and offer easy access to the many attractions and activities in the area. There are also many lodgings in Winchester that provide discounts for tourists. Many of these affordable accommodations are located near popular attractions and offer easy access to public transportation. In addition, there are a number of bed and breakfast establishments in the area that offer cheaper rates for guests. Airbnb is similarly a popular option for tourists seeking cheaper accommodations in Winchester. If you are looking for a cheap place to stay in Winchester, MA, you'll have a number of options available. With a little research, you can find a suitable room that fits your budget.

2 Star Average Prices: £132.27

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.

FAQs about hotels in Winchester

What are the best rated hotels in Winchester?

AC Hotel by Marriott Boston Cambridge, The Row Hotel at Assembly Row, Autograph Collection and enVision Hotel Boston - Everett, Ascend Hotel Collection are the best rated hotels based on customer reviews in the last 365 days.

What are the most up-scale hotels in Winchester?

Crowne Plaza Boston Woburn An Ihg Hotel, AC Hotel by Marriott Boston Cambridge and Freepoint Hotel Cambridge Tapestry Collection by Hilton are the top 3 luxury hotels near Winchester city center.

What hotels are closest to the city center of Winchester?

Hampton Inn Boston Woburn, The Inn At Woburn - Boston, and Best Western Plus New Englander are the properties closest to Winchester city center.

What are the best independent hotels in Winchester?

The Inn At Woburn - Boston, Porter Square Hotel and The Inn at Hastings Park, Relais & Chateaux - Boston are the best rated independent hotels (not part of a big brand).

What are the most popular Marriott hotels in Winchester?

Courtyard by Marriott Woburn, Fairfield Inn by Marriott Boston Woburn-Burlington and Residence Inn by Marriott Boston Burlington are the best rated Marriott/Starwood branded hotels (based on customer reviews score).

What are the best Choice Hotels branded hotels in Winchester?

enVision Hotel Boston - Everett, Ascend Hotel Collection, Quality Inn Boston - Revere and Quality Inn & Suites Lexington are the best rated Choice Hotels branded hotels (based on HotelPlanner reviews score).

What are the best IHG hotels in Winchester?

Crowne Plaza Boston Woburn An Ihg Hotel, Staybridge Suites Burlington Boston, an IHG Hotel and Holiday Inn Express Boston - Saugus are the best rated Intercontinental Hotel Group (IHG) branded hotels (based on user reviews score).

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