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

Hyatt Regency Boston One Ave. De Lafayette, Boston, MA 02111 +1-888-389-4121 ~8.05 miles southeast of Winchester
  • Four star hotel
  • 19 suites in hotel
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Excellent 9.0 /10 Hotel Reviews Call BookMore Details
Hilton Boston Park Plaza 50 Park Plaza, Boston, MA 02116 +1-888-675-2083 ~7.98 miles southeast of Winchester
  • High-end property
  • Pets Welcome
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Very Good 8.0 /10 Reviews Call BookMore Details
Boston Marriott Copley Place 110 Huntington Ave, Boston, MA 02116 +1-800-716-8490 ~8.04 miles southeast of Winchester
  • Four star hotel
  • 38 floors in property
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Excellent 9.2 /10 Reviews Call BookMore Details
The Langham Boston 250 Franklin St, Boston, MA 02110 +1-800-805-5223 ~8.03 miles southeast of Winchester
  • Luxurious 5-star hotel
  • Hotel has 17 suites
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Excellent 9.7 /10 Reviews Call BookMore Details
W Boston a Marriott Hotel 100 Stuart Street, Boston, MA 02116 +1-888-965-1860 ~8.09 miles southeast of Winchester
  • Four star hotel
  • Hotel has 15 floors
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Excellent 9.2 /10 Read Reviews Call BookMore Details
Seaport Hotel Boston 1 Seaport Lane, Boston, MA 02210 +1-888-788-5576 ~8.83 miles southeast of Winchester
  • 4-star hotel
  • Pets are Welcome
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Excellent 9.6 /10 Guest Reviews Call BookMore Details
Fairmont Copley Plaza Boston 138 Saint James Ave, Boston, MA 02116 +1-888-897-9207 ~7.97 miles southeast of Winchester
  • hotel
  • Fitness / Gym is on-site
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Very Good 8.9 /10 Hotel Reviews Call BookMore Details
YOTEL Boston Select by Hilton 65 Seaport Blvd, Boston, MA 02210 +1-888-311-4278 ~8.47 miles southeast of Winchester
  • Four-star hotel
  • 12 floors in hotel
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Very Good 8.3 /10 Review Score Call BookMore Details
The Bostonian Hotel Boston 26 North St, Boston, MA 02109 +1-888-469-4795 ~7.73 miles southeast of Winchester
  • 4-star hotel
  • Hotel has 201 rooms
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Average 7.8 /10 Recent Reviews Call BookMore Details
Sheraton Boston a Marriott Hotel 39 Dalton St, Boston, MA 02199 +1-888-734-9421 ~7.99 miles south of Winchester
  • High-end hotel
  • 29 floors in property
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Very Good 8.7 /10 Reviews Call BookMore Details
Omni Parker House 60 School St, Boston, MA 02108 +1-888-841-5292 ~7.81 miles southeast of Winchester
  • hotel
  • Pets are Welcome
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Very Good 8.9 /10 Recent Reviews Call BookMore Details
Omni Boston Hotel at the Seaport 450 Summer Street, Boston, MA 02210 +1-888-455-5160 ~8.90 miles southeast of Winchester
  • Luxurious Five Star hotel
  • 1054 sleeping rooms in hotel
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Excellent 9.1 /10 Guest Reviews Call BookMore Details
Hyatt Place Boston / Seaport District 295 NORTHERN AVENUE, Boston, MA 02210 +1-888-965-8297 ~9.04 miles southeast of Winchester
  • Three Star property
  • Fitness center on property
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Very Good 8.9 /10 Guest Reviews Call BookMore Details
The Godfrey Hotel Boston 505 Washington Street, Boston, MA 02111 +1-888-906-6358 ~7.95 miles southeast of Winchester
  • Four star hotel
  • 242 rooms in hotel
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Excellent 9.6 /10 Hotel Reviews Call BookMore Details
Hyatt Regency Boston / Cambridge 575 Memorial Drive, Cambridge, MA 02139 +1-888-749-6785 ~7.19 miles south of Winchester
  • Expensive hotel
  • Pet-friendly
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Excellent 9.0 /10 Recent Reviews Call BookMore Details
Hyatt Centric Faneuil Hall Boston 54 68 Devonshire St, Boston, MA 02109 +1-888-878-9982 ~7.85 miles southeast of Winchester
  • Expensive hotel
  • Check in: 4:00 PM - anytime
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Very Good 8.5 /10 Hotel Reviews Call BookMore Details
InterContinental Boston by IHG 510 Atlantic Ave, Boston, MA 02210 +1-888-389-4485 ~8.23 miles southeast of Winchester
  • Luxurious 5 Star hotel
  • Pets/Animals Allowed
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The Dagny Boston 89 Broad Street, Boston, MA 02110 +1-888-389-4121 ~8.01 miles southeast of Winchester
  • Expensive hotel
  • Hotel has 26 suites
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Club Quarters Hotel Faneuil Hall Boston 161 Devonshire St, Boston, MA 02110 +1-888-675-2083 ~7.96 miles southeast of Winchester
  • Expensive hotel
  • 16 suites in property
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Very Good 8.9 /10 Latest Reviews Call BookMore Details
Courtyard by Marriott Boston Downtown / North Station 107 Beverly St, Boston, MA 02114 +1-800-716-8490 ~7.34 miles southeast of Winchester
  • Affordable property
  • Check in: 4:00 PM - anytime
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Excellent 9.4 /10 Hotel Reviews Call BookMore Details
Boston Marriott Cambridge Two Cambridge Center 50 Broadway, Cambridge, MA 02142 +1-800-805-5223 ~6.87 miles southeast of Winchester
  • High-end hotel
  • Check in time: 4:00 PM - midnight
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Very Good 8.8 /10 Reviews Call BookMore Details
Raffles Boston 40 Trinity Place, Boston, MA 02116 +1-888-965-1860 ~8.04 miles southeast of Winchester
  • Luxury 5 star property
  • Pet-friendly
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Excellent 9.6 /10 Hotel Reviews Call BookMore Details
The Westin Copley Place Boston, a Marriott Hotel 10 Huntington Ave, Boston, MA 02116 +1-888-788-5576 ~7.99 miles southeast of Winchester
  • Expensive hotel
  • 803 sleeping rooms in hotel
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Excellent 9.2 /10 Latest Reviews Call BookMore Details
Canopy by Hilton Boston Downtown 99 Blackstone Street, Boston, MA 02109 +1-888-897-9207 ~7.69 miles southeast of Winchester
  • High-end property
  • 6 floors in property
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Excellent 9.1 /10 Recent Reviews Call BookMore Details
Encore Boston Harbor 1 Broadway, Everett, MA 02149 +1-888-311-4278 ~5.41 miles southeast of Winchester
  • Luxury Five Star property
  • Hotel has 671 rooms
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Excellent 9.5 /10 Latest Reviews Call BookMore Details
The Westin Boston Seaport District 425 Summer St, Boston, MA 02210 +1-888-469-4795 ~8.95 miles southeast of Winchester
  • Expensive hotel
  • Pets/Animals Allowed
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Hilton Boston Back Bay 40 Dalton St, Boston, MA 02115 +1-888-734-9421 ~7.99 miles south of Winchester
  • Four star property
  • Hotel has 401 rooms
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Boston Harbor Hotel 70 Rowes Wharf, Boston, MA 02110 +1-888-841-5292 ~8.16 miles southeast of Winchester
  • Luxurious 5-star property
  • Fitness / Gym is on-site
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Excellent 9.8 /10 Review Score Call BookMore Details
Copley Square Hotel a FOUND Hotel 47 Huntington Ave, Boston, MA 02116 +1-888-455-5160 ~7.97 miles southeast of Winchester
  • 4-star property
  • Hotel has an eco-friendly policy See policy
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Revere Hotel Boston Common 200 Stuart St, Boston, MA 02116 +1-888-965-8297 ~8.07 miles southeast of Winchester
  • 4 star hotel
  • Hotel has an eco-friendly policy See policy
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Renaissance Boston Seaport District 606 Congress St, Boston, MA 02210 +1-888-906-6358 ~8.93 miles southeast of Winchester
  • Expensive hotel
  • Hotel has 471 rooms
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Excellent 9.0 /10 Read Reviews Call BookMore Details
Element by Marriott Boston Seaport District 391 395 D Street, Boston, MA 02210 +1-888-749-6785 ~9.07 miles southeast of Winchester
  • 3 star property
  • Hotel has 180 rooms
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Very Good 8.8 /10 Guest Reviews Call BookMore Details
Hotel AKA Back Bay 154 Berkeley Street, Boston, MA 02116 +1-888-878-9982 ~8.04 miles southeast of Winchester
  • property
  • Check in: 4:00 PM - anytime
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Excellent 9.4 /10 Guest Reviews Call BookMore Details
citizenM Boston North Station 70 Causeway Street, Boston, MA 02114 +1-888-389-4485 ~7.30 miles southeast of Winchester
  • High end hotel
  • Check in: 2:00 PM - anytime
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Excellent 9.4 /10 Reviews Call BookMore Details
The Colonnade Hotel Back Bay 120 Huntington Avenue, Boston, MA 02116 +1-888-389-4121 ~8.11 miles south of Winchester
  • High-end property
  • 285 rooms in property
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Excellent 9.1 /10 Read Reviews Call BookMore Details
Pennyweight Hotel Boston Curio Collection by Hilton 155 Portland St, Boston, MA 02114 +1-888-675-2083 ~7.39 miles southeast of Winchester
  • High-end hotel
  • 112 sleeping rooms in hotel
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Very Good 8.5 /10 Recent Reviews Call BookMore Details
The Newbury Boston 15 Arlington St, Boston, MA 02116 +1-800-716-8490 ~7.84 miles southeast of Winchester
  • Luxury Five Star hotel
  • Hotel has 286 rooms
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Excellent 9.4 /10 Review Score Call BookMore Details
Aloft by Marriott Boston Seaport District 401 403 D Street, Boston, MA 02210 +1-800-805-5223 ~9.05 miles southeast of Winchester
  • Three Star hotel
  • Fitness + Health Center
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Very Good 8.8 /10 Recent Reviews Call BookMore Details
Wyndham Boston Beacon Hill 5 Blossom Street, Boston, MA 02114 +1-888-965-1860 ~7.40 miles southeast of Winchester
  • 3-star property
  • Hotel has 14 floors
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Average 7.1 /10 Reviews Call BookMore Details
The Royal Sonesta Boston 40 Edwin H. Land Boulevard, Cambridge, MA 02142 +1-888-788-5576 ~6.90 miles southeast of Winchester
  • 4 star property
  • Has environment-friendly policy Learn more
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Very Good 8.6 /10 Read Reviews Call BookMore Details
Harborside Inn of Boston 185 State St, Boston, MA 02109 +1-888-897-9207 ~7.92 miles southeast of Winchester
  • High-end property
  • Hotel has 8 floors
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Excellent 9.2 /10 Recent Reviews Call BookMore Details
DoubleTree by Hilton Boston - Downtown 821 Washington Street, Boston, MA 02111 +1-888-311-4278 ~8.24 miles southeast of Winchester
  • 4 star hotel
  • Gym / Fitness Center Available
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Very Good 8.3 /10 Recent Reviews Call BookMore Details
AC Hotel by Marriott Boston Downtown 225 Albany St, Boston, MA 02118 +1-888-469-4795 ~8.54 miles southeast of Winchester
  • 3-star property
  • 6 floors in hotel
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Very Good 8.8 /10 Hotel Reviews Call BookMore Details
Courtyard by Marriott Boston Downtown 275 Tremont St, Boston, MA 02116 +1-888-734-9421 ~8.14 miles southeast of Winchester
  • Three Star property
  • Check-in time: 3:00 PM - 3:00 AM
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Very Good 8.4 /10 Review Score Call BookMore Details
The Liberty a Marriott Luxury Collection Hotel, Boston 215 Charles St, Boston, MA 02114 +1-888-841-5292 ~7.29 miles southeast of Winchester
  • Luxury 5 star hotel
  • Pet-friendly
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Excellent 9.0 /10 Review Score Call BookMore Details
The Envoy Hotel Autograph Collection 70 Sleeper Street, Boston, MA 02210 +1-888-455-5160 ~8.36 miles southeast of Winchester
  • Four star hotel
  • Pets Allowed
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Excellent 9.0 /10 Reviews Call BookMore Details
Seaport Signal Building by Vacasa 154 West 2nd Street, Boston, MA 02127 +1-888-965-8297 ~8.95 miles southeast of Winchester
  • 4 star hotel
  • Check-in: 4:00 PM
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Excellent 10.0 /10 Guest Reviews Call BookMore Details
Moxy Boston Downtown 240 TREMONT STREET, Boston, MA 02116 +1-888-906-6358 ~8.10 miles southeast of Winchester
  • Three Star hotel
  • Check-in: 3:00 PM - midnight
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Very Good 8.4 /10 Guest Reviews Call BookMore Details
The Revolution Hotel 40 Berkeley Street, Boston, MA 02116 +1-888-749-6785 ~8.28 miles southeast of Winchester
  • Three Star property
  • Pet-friendly
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Excellent 9.0 /10 Reviews Call BookMore Details
Hotel AKA Boston Common 90 Tremont St, Boston, MA 02108 +1-888-878-9982 ~7.82 miles southeast of Winchester
  • Expensive hotel
  • Pets are Welcome
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Excellent 9.0 /10 Recent 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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