Find hotels in Winchester, MA from $85

Top reasons to visit Winchester

• Outdoor Activities: Enjoy parks and recreational areas perfect for family outings and nature walks.
• Rich History: Explore historic sites and landmarks that showcase Winchester's heritage.
• Charming Neighborhoods: Stroll through picturesque streets filled with friendly locals and unique shops.
• Proximity to Boston: Experience the vibrant city life and historical attractions just a short drive away.
• Diverse Accommodations: Choose from cozy bed & breakfasts to modern hotels, catering to various needs.

Find great hotels near Winchester

Discover a range of inviting accommodations in Winchester, Massachusetts, perfect for every traveler. From charming bed & breakfasts to modern hotels, you'll find options that cater to business needs, pet-friendly policies, and an LGBTQIA welcoming atmosphere. Explore the best hotels in the area, complete with glowing reviews and top-notch amenities, ensuring a memorable stay in this picturesque town.

• citizenM Boston North Station: Experience a modern and vibrant stay at citizenM Boston North Station, where contemporary design meets business efficiency. Located 7 miles from Winchester, this 4-star hotel is tailored for the savvy traveler. With a focus on accessibility and comfort, amenities include a 24-hour business center, meeting rooms, and a coworking space, making it ideal for professionals on the go. The hotel's LGBTQIA welcoming atmosphere, backed by its affiliation with LGBTQI travel guides, ensures all guests feel right at home.
• Hyatt Regency Boston/Cambridge: The Hyatt Regency Boston/Cambridge offers a sophisticated and versatile experience, just 7 miles from Winchester. This 4-star hotel is perfect for business travelers and their furry friends, as it is both pet-friendly and LGBTQIA welcoming. With a fully equipped conference space and a dedicated business district, the hotel caters to corporate needs while providing a comfortable environment. Enjoy the convenience of a variable pet policy and a range of amenities designed for guests traveling with pets.
• Four Points by Sheraton Boston Newton: Enjoy a blend of comfort and functionality at Four Points by Sheraton Boston Newton, situated 7 miles away from Winchester. This 3.5-star hotel welcomes both business and leisure travelers, offering a cozy atmosphere and essential business facilities, including a 24-hour accessible business center and conference spaces. The property also embraces a pet-friendly policy, allowing guests to travel with their pets (restrictions apply). With its ideal location and LGBTQIA welcoming stance, Four Points provides a welcoming experience for all.

Where to stay in Winchester

Winchester, Massachusetts, is a charming city perfect for family vacations and cultural exploration. Stroll through its picturesque neighborhoods, where friendly locals create a welcoming atmosphere. Enjoy outdoor activities in the nearby parks, or take a leisurely walk to discover local shops and eateries. Just a short drive away, Boston offers a rich historical backdrop, making it easy to blend urban adventures with the tranquility of Winchester. Experience the best of both worlds during your stay.

• Boston: As a vibrant metropolis, Boston is brimming with history and culture. Located a short distance from Winchester, this iconic city attracts travelers year-round, with peak visitors during the summer months and in October. Boston offers a diverse range of experiences, from educational institutions to lively music concerts and expansive shopping centers. Don't miss the chance to explore local landmarks like historic sports stadiums and conference venues, where you can immerse yourself in the rich sports culture and heritage of the city.
• Woburn: Just 2 miles away from Winchester, Woburn is a charming city that welcomes visitors with its family-friendly atmosphere. The city sees an influx of travelers in the spring and summer months, making it a lively stop on your journey. Woburn's attractions include shopping malls and local beaches, perfect for a day of relaxation or family fun. You can explore the local stadium or attend events at nearby conference venues, ensuring that there's always something to engage and entertain.
• West Medford: A quaint neighborhood located 2 miles from Winchester, West Medford is perfect for those seeking a cultural and outdoor experience. With seasonal visitor patterns peaking in spring and late fall, this area offers a unique blend of educational opportunities and shopping options. Explore the historic and modern college campuses that define this neighborhood, and take a stroll through its charming streets lined with historic buildings. West Medford is an ideal spot for those who appreciate a mix of culture and nature.

Things to do near Winchester

Winchester, Massachusetts, offers a delightful mix of outdoor activities and cultural experiences perfect for family vacations. Visitors can explore educational venues, enjoy shopping at the local mall, and even hit the nearby ski fields. For entertainment, there are various event venues and a movie theater to enjoy the latest films, making Winchester an ideal spot for a well-rounded getaway.

Shopping

In Winchester, you can shop at Wine & Cheese Cask for gourmet gifts, just 5 miles away. Harvard Square, 6 miles away, offers a vibrant shopping experience with entertainment. If you're up for a drive, visit Boston Public Market, located 7 miles away, for a taste of local flavors.

Recreation

Experience the lively atmosphere at MGM Music Hall at Fenway, just 8 miles from Winchester, where you can enjoy incredible concerts. For some sports action, visit Agganis Arena, 7 miles away, or have fun at Burlington Ice Palace, 3 miles away, perfect for ice skating and adventure.

Adventure

Explore the scenic beauty of Horn Pond, perfect for hiking and enjoying nature, located 2 miles from Winchester. For water sports enthusiasts, the Courageous Sailing Center offers thrilling sailing experiences 7 miles away. Experience the adrenaline rush of paintball at Boston Paintball, also situated 7 miles from Winchester.

Nightlife

Experience the adventure vibes at LEGOLAND® Discovery Center, just 5 miles away, or enjoy a romantic evening at Somerville Theatre, 4 miles from Winchester. For a lively atmosphere, head to Cambridge Common, a nearby pub perfect for drinks and entertainment with a romantic touch.

Booking tips and Expedia advantages for Winchester

To save money on your trip to Winchester, plan your visit between December and February for lower accommodation rates. Sundays are the most affordable days to stay, while Saturdays tend to be pricier. Use Expedia to customize your hotel search, filter for eco-friendly options, and sort by price for the best deals. Consider booking a package that includes flights and activities for additional savings. Joining Expedia's One Key membership can unlock exclusive discounts and allow you to earn cash for future bookings, enhancing your budget-friendly experience in Winchester.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winchester are December to February, where the prices are slightly lower. This is in comparison to May and September to October, where prices are slightly higher.
• The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winchester is Sunday. The most expensive day to stay in Winchester is Saturday.
• Find cheap hotels on Expedia: Utilize Expedia's search tool to customize your options, including your budget, preferred location, and the type of hotel you desire. For instance, selecting the Eco-certified filter will reveal sustainable and eco-friendly accommodations currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
• Consider bundling your trip: You can save money by booking an Expedia package that combines your hotel stay in Winchester with your flights and activities.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Winchester

Winchester, Massachusetts, is perfect for family vacations with a blend of outdoor activities and cultural experiences. Visitors can explore urban parks, historic colleges, and significant sites that highlight the town's rich history. These attractions offer a variety of engaging opportunities for families and travelers seeking both culture and city experiences, making Winchester a delightful destination for all ages.

• Fenway Park: Experience the vibrant atmosphere of this iconic baseball stadium, just 8 miles from Winchester. With its rich history and passionate fans, Fenway Park is a must-visit for sports enthusiasts and culture lovers alike.
• Harvard University: Located 6 miles from Winchester, Harvard University offers a glimpse into one of the world's most prestigious educational institutions. Stroll through its historic campus and soak in the intellectual culture that has shaped generations.
• TD Garden: Just 7 miles away, TD Garden is a premier venue for concerts and sporting events. Enjoy the dynamic energy of this multifaceted space that hosts everything from NHL games to major concerts, perfect for business and entertainment.

Best time to go to Winchester

The best time to visit Winchester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	28.6°F (-1.9°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	29.8°F (-1.2°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
March	36.9°F (2.7°C)	Light Rain	Mostly Sunny	Average	Average
April	47.7°F (8.7°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	58.3°F (14.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	66.4°F (19.1°C)	Light Rain	Mostly Sunny	Average	Average
July	73.6°F (23.1°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	72.3°F (22.4°C)	Light Rain	Mostly Sunny	Average	Average
September	65.3°F (18.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
October	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	43.3°F (6.3°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	35.1°F (1.7°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low

The nearest major airports for your trip to Winchester

For your visit to Winchester, Massachusetts, the closest major airport is Boston Logan International Airport (BOS), situated 9 miles away. Recommended hotels nearby include the 5-star Encore Boston Harbor, 3 miles from the airport, and The Langham, Boston, 2 miles away, as well as The Liberty, a Marriott Luxury Collection Hotel, also 3 miles away. Providence T.F. Green Airport (PVD) is 53 miles from Winchester, with options like the Omni Providence Hotel, Graduate by Hilton Providence, and Renaissance Providence Downtown Hotel, all 7 miles from the airport. Lastly, Manchester-Boston Regional Airport (MHT) is 36 miles away, offering stays at The Grand at Bedford Village Inn and DoubleTree by Hilton Manchester Downtown, both 4 miles from the airport.