Find hotels in Winchester, MA from ￥15,565

Top reasons to visit Winchester

• Outdoor Adventures: Winchester offers a variety of outdoor activities in its urban parks, perfect for family vacations.
• Rich History: Explore historical sites that showcase the town's rich heritage, providing a glimpse into New England's past.
• Charming Neighborhoods: Stroll through welcoming neighborhoods filled with local culture and friendly locals.
• Variety of Accommodations: Enjoy a range of lodging options, from cozy bed and breakfasts to hotels with modern amenities.
• Family-Friendly Activities: Engage in educational experiences, shopping, and nearby theaters that cater to all ages.

Find great hotels near Winchester

Discover a range of welcoming accommodations in Winchester, Massachusetts, perfect for every traveler. From comfortable hotels to charming bed and breakfasts, you'll find options that cater to business needs, are pet-friendly, and embrace an LGBTQIA-friendly atmosphere. Whether you're looking for hotels near Winchester or specific amenities like swimming facilities, Winchester offers a delightful stay for all visitors.

• citizenM Boston North Station: Located 11km from Winchester, citizenM Boston North Station is a modern 4-star hotel that combines comfort with a unique design ethos. Known for its vibrant and stylish atmosphere, this hotel caters especially to business travelers. Guests appreciate the contemporary, tech-savvy rooms equipped with mood lighting, smart TVs, and plush bedding. The hotel also features a 24/7 canteenM, offering freshly prepared meals and drinks, making it an ideal spot for those on the go.
• Hyatt Regency Boston/Cambridge: Situated 11km from Winchester, the Hyatt Regency Boston/Cambridge is a 4-star property that welcomes both business and leisure travelers, including pets. This hotel boasts spacious rooms with stunning views of the Charles River and Boston skyline. Guests enjoy amenities such as a fitness center, on-site dining, and a pet-friendly policy that allows dogs with certain restrictions. The hotel’s emphasis on comfort and convenience makes it a popular choice for travelers seeking a blend of professional and personal experiences.
• Four Points by Sheraton Boston Newton: Located 11km from Winchester, Four Points by Sheraton Boston Newton is a family-friendly 3.5-star hotel that offers a warm and inviting atmosphere. With amenities tailored for families, including free cribs and a video game console, it ensures a comfortable stay for guests of all ages. The hotel also features romantic packages for couples, along with access to an indoor pool and spa services, providing a relaxing getaway. Guests appreciate the combination of business amenities and family-friendly services, making it an excellent option for diverse travel needs.

Where to stay in Winchester

Winchester, Massachusetts offers a delightful blend of outdoor adventures and family-friendly activities. Stroll through its charming neighborhoods, where a warm, welcoming atmosphere awaits. Explore nearby cities and historical sites, perfect for a weekend getaway. With a vibrant urban vibe and friendly locals, Winchester provides a unique experience that captures the essence of New England. Whether you're seeking relaxation or exploration, this lovely town has something for everyone.

• Boston: Boston, the vibrant capital of Massachusetts, is a bustling metropolis that offers a diverse range of experiences for travelers. Situated close to Winchester, it attracts visitors year-round, especially during the peak months of July, August, and October. Known for its rich history and culture, Boston is perfect for those seeking city-themed adventures or family outings. Explore iconic landmarks such as historic sports stadiums and event venues, or indulge in shopping at popular malls. With its renowned educational institutions and lively music scene, Boston promises an unforgettable urban experience.
• Woburn: Located a mere 3km from Winchester, Woburn is a charming city that provides a blend of business and family-friendly attractions. Visitor numbers peak in April, July, and September, making it a great stop year-round. Woburn is known for its shopping centers and educational venues, offering easy access to local amenities. Don't miss the historic college universities and beautiful beaches nearby, perfect for relaxing after a day of exploration. With its welcoming atmosphere, Woburn is a delightful addition to your itinerary.
• Cambridge: Just 10km from Winchester, Cambridge is known for its prestigious universities and vibrant cultural scene. The city attracts a steady flow of visitors, particularly in April, July, and September. Cambridge is ideal for those interested in a mix of city-themed, family, and business experiences. You can enjoy shopping at local centers and explore historic sites, including renowned colleges and sports stadiums. Its unique blend of academic energy and artistic flair makes Cambridge a must-visit destination during your trip.

Things to do in Winchester

Shopping

In Winchester, explore local shops like the charming Winchester Farmers Market for unique gifts. If you're up for a drive, head to the nearby Square One Mall for a wider selection of retail stores and dining options to enhance your shopping experience.

Recreation

Experience the tranquility of the Winchester Wellness Center, where you can enjoy yoga classes and holistic treatments designed to rejuvenate your mind and body. For outdoor activity, the nearby Horn Pond offers scenic walking trails and a peaceful environment for relaxation and reflection.

Adventure

Explore the scenic trails of the Middlesex Fells Reservation, offering hiking and biking paths with beautiful views of the landscape. For a unique adventure, try kayaking on the Shawsheen River, where you can experience nature up close and enjoy the tranquility of the water.

Nightlife

In Winchester, the Winchester Pub offers a cozy atmosphere with craft beers and live music, making it a great spot to unwind. Nearby, the Caffe Nero serves coffee and pastries late into the evening, perfect for a relaxed night out with friends.

Find the best attractions near Winchester

Winchester, Massachusetts, is perfect for outdoor and family-themed vacations, offering a blend of urban parks, historic sites, and vibrant streets. Visitors can immerse themselves in the local culture while enjoying outdoor activities. Key attractions include Winchester Hospital and nearby swimming facilities, as well as charming resorts for a relaxing stay. With its rich history and beautiful landscapes, Winchester provides an ideal getaway for travelers seeking both adventure and leisure.

• Fenway Park: Experience the excitement of America’s pastime at this historic sports stadium, home to the Boston Red Sox. With its iconic Green Monster and rich history, Fenway Park offers a unique atmosphere that blends sports culture with local tradition.
• Boston Common: Enjoy a leisurely stroll or a family picnic in Boston's oldest public park. This urban oasis features beautiful landscapes and walking paths, making it a lovely spot to relax and take in the vibrant city life.
• Newbury Street: Explore this charming street known for its boutique shops and cafes. With its historic brownstones and lively atmosphere, Newbury Street is perfect for a leisurely afternoon of shopping and dining.

Best time to go to Winchester

The best time to visit Winchester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winchester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Winchester falls in January, 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

When planning your visit to Winchester, Massachusetts, you have several airport options. BOSton Logan International Airport (BOS) is the closest, located 14km away. Nearby hotels include the 5-star Encore Boston Harbor, InterContinental Boston, and The Langham, all within 5km of the airport. Hartford Bradley International Airport (BDL) is 140km from Winchester, with good accommodations like the DoubleTree by Hilton Hartford located 2km away. Providence T.F. Green Airport (PVD) is 85km away, offering hotels such as the Omni Providence and Graduate by Hilton, both 11km from the airport. Transportation services are available from these hotels to their respective airports for convenience.