Winchester Hotels

Top reasons to visit Winchester

• Charming Streets: Stroll through the picturesque streets of Winchester, where friendly locals create a welcoming atmosphere.
• Historical Attractions: Explore significant historical sites and nearby cities, immersing yourself in rich local heritage.
• Urban Parks: Enjoy leisurely walks in serene parks, perfect for relaxation and appreciating nature.
• Diverse Accommodation: Choose from a variety of charming hotels and bed & breakfasts, catering to all types of travellers.
• Entertainment Options: Indulge in local shopping centres, a movie theatre, and event venues for lively entertainment.

Find great hotels near Winchester

Discover the charming accommodation options in Winchester, Massachusetts, where a variety of hotels and bed & breakfasts await your arrival. Whether you're seeking a pet-friendly stay, a welcoming atmosphere for LGBTQIA travellers, or business-oriented facilities, Winchester offers a delightful selection of top-rated hotels. With exceptional reviews and diverse lodging types, you're sure to find the perfect base for your American adventure.

• citizenM Boston North Station: Emphasising a modern and vibrant atmosphere, citizenM Boston North Station is an ideal choice for savvy travellers seeking a blend of business and leisure. This 4-star hotel boasts stylish, tech-savvy rooms designed for ultimate comfort, with amenities including free Wi-Fi, smart TVs, and mood lighting. Its LGBTQIA-friendly environment ensures a welcoming experience for all guests. Located a mere 11.3km from Winchester, this hotel also offers easy access to Boston’s bustling attractions and business districts, making it perfect for both work and play.
• Hyatt Regency Boston/Cambridge: A perfect blend of comfort and convenience, Hyatt Regency Boston/Cambridge is a 4-star hotel that caters to diverse travellers, including those with pets. With a pet-friendly policy and amenities such as a gym, business centre, and on-site dining, guests can enjoy a relaxed yet productive stay. The hotel embraces an LGBTQIA-friendly ethos, ensuring inclusivity for all. Situated 11.3km from Winchester, the hotel’s scenic views of the Charles River and proximity to Cambridge’s vibrant culture make it a superb choice for both leisure and business travellers.
• Four Points by Sheraton Boston Newton: Ideal for those seeking a romantic getaway, Four Points by Sheraton Boston Newton offers a serene escape immersed in nature. This 3.5-star hotel features charming accommodations and a range of amenities, including an indoor pool and spa services, perfect for couples looking to unwind. With romance packages available, guests can indulge in a unique experience tailored to their needs. Just 11.3km from Winchester, the hotel’s tranquil setting and attentive staff ensure a memorable stay, making it a lovely choice for a romantic vacation.

Where to stay in Winchester

Winchester, Massachusetts, offers a delightful blend of charm and urban atmosphere, perfect for families and business travellers alike. Stroll through its picturesque streets, where friendly locals enhance the welcoming vibe. Explore nearby cities for a rich historical experience, or enjoy leisurely walks in the serene parks. With a variety of attractions within walking distance, your visit promises to be both enriching and enjoyable.

• Boston: As a vibrant metropolis, Boston is the heart of Massachusetts, brimming with culture and history. Situated a short distance from Winchester, it attracts visitors year-round, with peak arrivals during the summer months and October. Known for its rich educational landscape, Boston is home to renowned universities and historic landmarks. You can immerse yourself in an array of activities including music concerts, shopping at bustling malls, and exploring historic sports stadiums. The city's unique blend of historic charm and modern amenities creates an enticing travel experience, making it a must-visit destination.
• Cambridge: Located approximately 9.7km from Winchester, Cambridge is a city that exudes an intellectual aura, largely due to its prestigious universities. With a steady influx of tourists, particularly in the spring and summer, it offers a family-friendly atmosphere alongside rich cultural experiences. Visitors can enjoy a vibrant shopping scene, with various centres and local boutiques. The presence of historic universities and sports venues adds to the city's allure, ensuring that there's always something interesting to explore, whether you're wandering along the scenic Charles River or indulging in local cuisine.
• Woburn: Just 3.2km from Winchester, Woburn is a charming city that welcomes families and business travellers alike. While its visitor numbers remain consistent throughout the year, the city sees a surge in activity during the warmer months. Woburn offers a delightful mix of shopping centres and educational venues, making it an ideal spot for leisurely explorations. It is also home to historic landmarks and event venues, which enrich the local experience. With its close proximity to both Boston and Cambridge, Woburn serves as a convenient base for exploring the rich history and culture of the Greater Boston area.

Things to do near Winchester

Winchester, Massachusetts, offers a delightful blend of activities for city-themed, family, and business vacations. Visitors can enjoy educational attractions, explore local shopping centres, and indulge in a variety of entertainment options, including a movie theatre and event venues. Whether you're seeking leisure or vibrant social experiences, Winchester presents a charming backdrop for a memorable stay.

Shopping

In Winchester, you can enjoy shopping at Bow Market, just 8.0km away, offering a delightful mix of local businesses. Harvard Square, located 9.7km away, features a vibrant atmosphere with entertainment options. If you're up for a drive, the Boston Public Market is 11.3km away, showcasing local produce and crafts.

Recreation

Experience the vibrant atmosphere at MGM Music Hall at Fenway, where live music fills the air, just 12.9km from Winchester. For sports enthusiasts, Nickerson Field offers thrilling events 11.3km away, while the Paradise Rock Club, also 11.3km from Winchester, promises unforgettable concerts in an intimate setting.

Adventure

Explore Horn Pond, located 3.2km from Winchester, for a serene outdoor experience with scenic trails and nature. For water sports, head to Courageous Sailing Center, 11.3km away, where adventure awaits on the water. Alternatively, enjoy thrills at Boston Paintball, also 11.3km from Winchester.

Nightlife

In Winchester, LEGOLAND® Discovery Center provides a fun-filled family atmosphere with exciting arcade games just 8.0km away. Meanwhile, Somerville Theatre offers a romantic cultural experience 6.4km away, while Cambridge Common combines entertainment and romance in a charming pub setting, also 8.0km distant.

Booking tips and Expedia advantages for Winchester

To save money during your visit to Winchester, consider travelling between December and February, when accommodation prices are lower. Sundays typically offer the best rates, while Saturdays are the priciest. Utilise Expedia’s search tool to find budget-friendly options and combine your hotel, flights, and activities for additional savings. For public transport, take advantage of affordable options, and explore free activities in the area to maximise your experience without overspending.

• 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: Utilise Expedia's search tool to refine your preferences, such as your budget, desired location, and preferred type of accommodation. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
• Consider bundling your trip: You can enjoy significant savings by combining your hotel reservations in Winchester with your flights and activities through an Expedia package.

Find the best attractions near Winchester

Winchester, Massachusetts, is an ideal destination for city-themed, family, and business holidays. Visitors can explore a variety of attractions, including urban parks, historic colleges and universities, and significant historical sites. This charming locale offers a delightful blend of cultural experiences and urban adventures, ensuring that travellers seeking family-friendly activities and rich history will find plenty to enjoy during their stay.

• Fenway Park: Experience the rich history and vibrant atmosphere of Fenway Park, the iconic baseball stadium known for its passionate fans and classic charm. With its unique features like the Green Monster, it offers an unforgettable sports culture experience.
• Harvard University: Wander through the historic campus of Harvard University, where academic excellence and cultural heritage converge. Its stunning architecture and rich history provide a captivating glimpse into one of the world’s most prestigious institutions.
• Boston Common: Enjoy the expansive greenery of Boston Common, the oldest city park in the United States. Ideal for families, it offers recreational activities, scenic walks, and a lively urban atmosphere, perfect for relaxation amidst the bustling city.

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

To reach Winchester, Massachusetts, consider flying into one of three major airports. Boston Logan International Airport (BOS) is situated 14.5km away, with excellent nearby hotels such as the InterContinental Boston, Encore Boston Harbor, and Boston Harbor Hotel, all within 4.8km. Providence T.F. Green Airport (PVD) is 54.8km distant, with options like the Omni Providence Hotel and Hotel Providence, both 11.3km from the airport. Alternatively, Manchester-Boston Regional Airport (MHT) is 57.9km from Winchester, offering hotels like the DoubleTree by Hilton Manchester Downtown and EVEN Hotels Manchester Airport, conveniently located 4 and 3.2km away respectively.