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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

Hyatt Regency Boston One Ave. De Lafayette, Boston, MA 02111 ~8.05 miles southeast of Winchester
  • 4 star hotel
  • 502 rooms in hotel
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Hilton Boston Park Plaza 50 Park Plaza, Boston, MA 02116 ~7.98 miles southeast of Winchester
  • High-end property
  • Pets Allowed
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Very Good 8.0 /10 Reviews Call BookMore Details
Boston Marriott Copley Place 110 Huntington Ave, Boston, MA 02116 ~8.04 miles southeast of Winchester
  • 4 star hotel
  • Gym / Fitness Center Available
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Excellent 9.2 /10 Read Reviews Call BookMore Details
The Langham Boston 250 Franklin St, Boston, MA 02110 ~8.03 miles southeast of Winchester
  • Luxury Five Star property
  • 17 suites in property
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Excellent 9.7 /10 Reviews Call BookMore Details
W Boston a Marriott Hotel 100 Stuart Street, Boston, MA 02116 ~8.09 miles southeast of Winchester
  • Four star property
  • Check-in time: 4:00 PM - 5:30 AM
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Excellent 9.2 /10 Read Reviews Call BookMore Details
Seaport Hotel Boston 1 Seaport Lane, Boston, MA 02210 ~8.83 miles southeast of Winchester
  • 4 star hotel
  • Check in: 3:00 PM - 2:00 AM
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Excellent 9.6 /10 Read Reviews Call BookMore Details
Fairmont Copley Plaza Boston 138 Saint James Ave, Boston, MA 02116 ~7.97 miles southeast of Winchester
  • hotel
  • 383 sleeping rooms in hotel
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Very Good 8.9 /10 Read Reviews Call BookMore Details
YOTEL Boston Select by Hilton 65 Seaport Blvd, Boston, MA 02210 ~8.47 miles southeast of Winchester
  • 4-star property
  • 326 rooms in property
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Very Good 8.3 /10 Read Reviews Call BookMore Details
The Bostonian Hotel Boston 26 North St, Boston, MA 02109 ~7.73 miles southeast of Winchester
  • Four-star property
  • 17 suites in hotel
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Average 7.8 /10 Read Reviews Call BookMore Details
Sheraton Boston a Marriott Hotel 39 Dalton St, Boston, MA 02199 ~7.99 miles south of Winchester
  • High end property
  • Pet-friendly
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Omni Parker House 60 School St, Boston, MA 02108 ~7.81 miles southeast of Winchester
  • hotel
  • 15 floors in hotel
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Very Good 8.9 /10 Reviews Call BookMore Details
Omni Boston Hotel at the Seaport 450 Summer Street, Boston, MA 02210 ~8.90 miles southeast of Winchester
  • Luxury Five Star hotel
  • 21 suites in hotel
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Excellent 9.1 /10 Review Score Call BookMore Details
Hyatt Place Boston / Seaport District 295 NORTHERN AVENUE, Boston, MA 02210 ~9.04 miles southeast of Winchester
  • 3 star hotel
  • 297 rooms in property
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The Godfrey Hotel Boston 505 Washington Street, Boston, MA 02111 ~7.95 miles southeast of Winchester
  • 4-star hotel
  • Access to gym on-site
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Excellent 9.6 /10 Guest Reviews Call BookMore Details
Hyatt Regency Boston / Cambridge 575 Memorial Drive, Cambridge, MA 02139 ~7.19 miles south of Winchester
  • High-end property
  • Hotel has 16 floors
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Hyatt Centric Faneuil Hall Boston 54 68 Devonshire St, Boston, MA 02109 ~7.85 miles southeast of Winchester
  • 4 star 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 ~8.23 miles southeast of Winchester
  • Luxurious Five Star hotel
  • Pets are Allowed
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The Dagny Boston 89 Broad Street, Boston, MA 02110 ~8.01 miles southeast of Winchester
  • 4 star hotel
  • 14 floors in property
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Club Quarters Hotel Faneuil Hall Boston 161 Devonshire St, Boston, MA 02110 ~7.96 miles southeast of Winchester
  • 4-star property
  • Hotel has 16 suites
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Very Good 8.9 /10 Hotel Reviews Call BookMore Details
Courtyard by Marriott Boston Downtown / North Station 107 Beverly St, Boston, MA 02114 ~7.34 miles southeast of Winchester
  • Mid-scale property
  • Check in: 4:00 PM - anytime
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Excellent 9.4 /10 Latest Reviews Call BookMore Details
Boston Marriott Cambridge Two Cambridge Center 50 Broadway, Cambridge, MA 02142 ~6.87 miles southeast of Winchester
  • Expensive hotel
  • 26 floors in hotel
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Very Good 8.8 /10 Hotel Reviews Call BookMore Details
Raffles Boston 40 Trinity Place, Boston, MA 02116 ~8.04 miles southeast of Winchester
  • Luxurious 5-star property
  • 35 floors in hotel
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Excellent 9.6 /10 Latest Reviews Call BookMore Details
The Westin Copley Place Boston, a Marriott Hotel 10 Huntington Ave, Boston, MA 02116 ~7.99 miles southeast of Winchester
  • 4-star hotel
  • 803 rooms in property
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Excellent 9.2 /10 Latest Reviews Call BookMore Details
Canopy by Hilton Boston Downtown 99 Blackstone Street, Boston, MA 02109 ~7.69 miles southeast of Winchester
  • Four star property
  • 212 rooms in hotel
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Excellent 9.1 /10 Read Reviews Call BookMore Details
Encore Boston Harbor 1 Broadway, Everett, MA 02149 ~5.41 miles southeast of Winchester
  • Luxurious Five Star hotel
  • Check in time: 4:00 PM - midnight
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The Westin Boston Seaport District 425 Summer St, Boston, MA 02210 ~8.95 miles southeast of Winchester
  • High-end property
  • 16 floors in hotel
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Hilton Boston Back Bay 40 Dalton St, Boston, MA 02115 ~7.99 miles south of Winchester
  • High-end hotel
  • Pets are Welcome
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Boston Harbor Hotel 70 Rowes Wharf, Boston, MA 02110 ~8.16 miles southeast of Winchester
  • Luxurious 5-star hotel
  • 232 rooms in property
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Copley Square Hotel a FOUND Hotel 47 Huntington Ave, Boston, MA 02116 ~7.97 miles southeast of Winchester
  • Expensive hotel
  • Check in: 3:00 PM - 2:00 AM
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Very Good 8.6 /10 Guest Reviews Call BookMore Details
Revere Hotel Boston Common 200 Stuart St, Boston, MA 02116 ~8.07 miles southeast of Winchester
  • High-end property
  • Has environment-friendly policy Read more
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Renaissance Boston Seaport District 606 Congress St, Boston, MA 02210 ~8.93 miles southeast of Winchester
  • High-end hotel
  • Hotel has 21 suites
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Element by Marriott Boston Seaport District 391 395 D Street, Boston, MA 02210 ~9.07 miles southeast of Winchester
  • Three Star hotel
  • Hotel has an eco-friendly policy See more
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Very Good 8.8 /10 Reviews Call BookMore Details
Hotel AKA Back Bay 154 Berkeley Street, Boston, MA 02116 ~8.04 miles southeast of Winchester
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  • Check in: 4:00 PM - anytime
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citizenM Boston North Station 70 Causeway Street, Boston, MA 02114 ~7.30 miles southeast of Winchester
  • 4-star hotel
  • Check-in time: 2:00 PM - anytime
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The Colonnade Hotel Back Bay 120 Huntington Avenue, Boston, MA 02116 ~8.11 miles south of Winchester
  • High end property
  • Hotel has 9 suites
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Excellent 9.2 /10 Review Score Call BookMore Details
Pennyweight Hotel Boston Curio Collection by Hilton 155 Portland St, Boston, MA 02114 ~7.39 miles southeast of Winchester
  • High-end property
  • Hotel has 11 floors
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Very Good 8.4 /10 Latest Reviews Call BookMore Details
The Newbury Boston 15 Arlington St, Boston, MA 02116 ~7.84 miles southeast of Winchester
  • Luxury 5 star property
  • 286 sleeping rooms in hotel
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Aloft by Marriott Boston Seaport District 401 403 D Street, Boston, MA 02210 ~9.05 miles southeast of Winchester
  • Three Star property
  • Gym / Fitness Center Available
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Very Good 8.8 /10 Latest Reviews Call BookMore Details
Wyndham Boston Beacon Hill 5 Blossom Street, Boston, MA 02114 ~7.40 miles southeast of Winchester
  • Three Star hotel
  • Check-in: 4:00 PM - anytime
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Average 7.1 /10 Latest Reviews Call BookMore Details
The Royal Sonesta Boston 40 Edwin H. Land Boulevard, Cambridge, MA 02142 ~6.90 miles southeast of Winchester
  • High-end property
  • 400 rooms in property
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Very Good 8.6 /10 Hotel Reviews Call BookMore Details
Harborside Inn of Boston 185 State St, Boston, MA 02109 ~7.92 miles southeast of Winchester
  • High end property
  • 8 floors in property
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Excellent 9.2 /10 Recent Reviews Call BookMore Details
DoubleTree by Hilton Boston - Downtown 821 Washington Street, Boston, MA 02111 ~8.24 miles southeast of Winchester
  • High-end property
  • Fitness / Gym is on-site
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Very Good 8.3 /10 Latest Reviews Call BookMore Details
AC Hotel by Marriott Boston Downtown 225 Albany St, Boston, MA 02118 ~8.54 miles southeast of Winchester
  • Mid-scale property
  • Hotel has a green policy See more
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Courtyard by Marriott Boston Downtown 275 Tremont St, Boston, MA 02116 ~8.14 miles southeast of Winchester
  • 3-star hotel
  • 315 rooms in hotel
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Very Good 8.4 /10 Read Reviews Call BookMore Details
The Liberty a Marriott Luxury Collection Hotel, Boston 215 Charles St, Boston, MA 02114 ~7.29 miles southeast of Winchester
  • Luxury 5-star hotel
  • 16 floors in hotel
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Excellent 9.0 /10 Hotel Reviews Call BookMore Details
The Envoy Hotel Autograph Collection 70 Sleeper Street, Boston, MA 02210 ~8.36 miles southeast of Winchester
  • Expensive hotel
  • Pets are Welcome
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Seaport Signal Building by Vacasa 154 West 2nd Street, Boston, MA 02127 ~8.95 miles southeast of Winchester
  • 4-star hotel
  • Check in: 4:00 PM
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Excellent 10.0 /10 Review Score Call BookMore Details
Moxy Boston Downtown 240 TREMONT STREET, Boston, MA 02116 ~8.10 miles southeast of Winchester
  • Three Star hotel
  • Check-in time: 3:00 PM - midnight
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Very Good 8.4 /10 Read Reviews Call BookMore Details
The Revolution Hotel 40 Berkeley Street, Boston, MA 02116 ~8.28 miles southeast of Winchester
  • 3-star property
  • Pets are Allowed
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Excellent 9.0 /10 Latest Reviews Call BookMore Details
Hotel AKA Boston Common 90 Tremont St, Boston, MA 02108 ~7.82 miles southeast of Winchester
  • High-end property
  • 5 suites in hotel
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Excellent 9.0 /10 Read 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.

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: $175.57

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: $155.07

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: $117.00

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 top rated hotels in Winchester?

Seaport Signal Building by Vacasa, The Langham Boston and Boston Harbor Hotel are the best rated hotels based on customer reviews in the last 365 days.

What are the 4-5 star hotels in Winchester?

The Langham Boston, Omni Boston Hotel at the Seaport and InterContinental Boston by IHG are the top 3 luxury hotels near Winchester city center.

What hotels are closest to the city center of Winchester?

Encore Boston Harbor, Boston Marriott Cambridge, and The Royal Sonesta Boston are the properties closest to Winchester city center.

What are the best independent hotels in Winchester?

Boston Yacht Haven Inn & Marina, Seaport Signal Building by Vacasa and Tuxbury Pond Camping Resort Tiny House Riley are the best rated independent hotels (not part of a big brand).

What are the best Marriott hotels in Winchester?

Residence Inn by Marriott Boston Natick, Residence Inn by Marriott Boston Downtown and Residence Inn by Marriott Boston Braintree are the best rated Marriott/Starwood branded hotels (based on customer reviews score).

What are the most popular Choice Hotels branded hotels in Winchester?

Cambria Hotel Boston Somerville, Cambria Hotel & Suites Plymouth and Econo Lodge Inn & Suites are the best rated Choice Hotels branded hotels (based on HotelPlanner reviews score).

What are the most popular Best Western hotels in Winchester?

Best Western Plus New Englander, Best Western Plus Cold Spring and Best Western Plus North Shore Hotel are the best rated Best Western branded hotels (based on user reviews score).

What are the best IHG hotels in Winchester?

Holiday Inn Express Boston Logan Airport - Revere by IHG, Holiday Inn Express Boston - Waltham by IHG and Kimpton Marlowe Hotel by IHG are the best rated Intercontinental Hotel Group (IHG) branded hotels (based on user reviews score).

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