Find hotels in Winchester, MA from £68

Top reasons to visit Winchester

• Scenic Outdoor Activities: Winchester offers a variety of outdoor pursuits, including lovely parks and recreational areas perfect for families.
• Rich Historical Sites: Explore charming attractions like the Winchester Discovery Centre and historic landmarks, including Winchester Cathedral.
• Vibrant Local Culture: Wander through picturesque streets and immerse yourself in the friendly atmosphere of the town.
• Diverse Accommodation Options: Choose from hotels and charming B&Bs, catering to all travellers, including pet-friendly and LGBTQIA-friendly stays.
• Convenient Location: Winchester is ideally situated for day trips and easy access to nearby skiing and shopping.

Find great hotels near Winchester

Discover a range of accommodation options in Winchester, Massachusetts, perfect for every type of traveller. Whether you're seeking a convenient hotel for business or a charming bed & breakfast for a relaxing getaway, Winchester offers pet-friendly and LGBTQIA welcoming stays. From budget-friendly options to more luxurious experiences, you'll find the ideal place to unwind and explore this delightful town.

• citizenM Boston North Station: Emphasising a modern and innovative design, citizenM Boston North Station is a 4-star hotel that caters to business travellers seeking a vibrant and inclusive atmosphere. Located 4.3km from Winchester, this hotel is proud to welcome the LGBTQIA community and offers dedicated facilities such as a 24-hour business centre, meeting rooms, and coworking spaces. With a commitment to comfort, citizenM ensures guests enjoy contemporary rooms equipped with all the essentials for a productive stay, making it an excellent choice for professionals on the go.
• Extended Stay America Suites - Boston - Saugus: For those looking for adventure, Extended Stay America Suites - Boston - Saugus, situated 3.7km from Winchester, offers a unique blend of excitement and comfort. This pet-friendly accommodation is welcoming to the LGBTQIA community and provides opportunities for outdoor activities such as scooter rentals, ice skating, and horse riding nearby. The hotel features essential amenities for longer stays, making it ideal for guests who wish to explore the surrounding area while enjoying a home-like atmosphere.
• Hyatt Regency Boston/Cambridge: A refined choice for both business and leisure travellers, Hyatt Regency Boston/Cambridge is located 4.3km from Winchester. This 4-star hotel offers a seamless blend of professionalism and pet-friendly policies, welcoming the LGBTQIA community with open arms. Guests can benefit from conference spaces and other business amenities while enjoying the hotel's luxurious features. With a commitment to service and comfort, Hyatt Regency is perfect for those seeking an elegant environment paired with the convenience of being close to the vibrant city life.

Where to stay near Winchester

Winchester, Massachusetts, offers a delightful blend of outdoor activities and cultural experiences, making it ideal for family vacations. Explore the charming streets of Winchester city and immerse yourself in its friendly atmosphere. Just a short walk away, you can discover the vibrant local culture and historical sights. Whether you're wandering through picturesque neighbourhoods or enjoying the lush parks, Winchester promises an enriching getaway for all ages.

• Boston: A vibrant metropolis located 5.0km from Winchester, Boston is renowned for its rich history and cultural diversity. Visitors can immerse themselves in a plethora of experiences, from educational institutions to lively music concerts and expansive shopping malls. The city’s landmarks, such as historic sports stadiums and conference venues, offer a glimpse into its sporting heritage and community events. With traveller numbers peaking in the summer and autumn, Boston is a bustling hub for family adventures and cultural exploration.
• Woburn: Situated a mere 1.2km from Winchester, Woburn is a charming city that attracts visitors throughout the year. Known for its family-friendly atmosphere and cultural experiences, Woburn boasts an array of shopping centres and educational venues. Its local attractions include beach areas and event conference venues, providing a perfect backdrop for leisure and entertainment. Peak travel seasons in April, July, and September bring a lively atmosphere, making Woburn an inviting destination for all.
• West Medford: Just 1.2km from Winchester, West Medford is a picturesque neighbourhood known for its cultural and outdoor experiences. The area draws seasonal visitors, particularly in spring and late autumn. With a blend of educational institutions and shopping areas, West Medford offers a relaxed yet vibrant atmosphere. Notable landmarks include historic buildings and modern colleges, making it an intriguing destination for those interested in history and education, as well as outdoor pursuits.

Things to do near Winchester

Winchester, Massachusetts, is perfect for outdoor and cultural family vacations. Visitors can enjoy various activities, including educational experiences, shopping at the local mall, and skiing at nearby fields. For those looking for a day trip, Winchester offers a charming blend of leisure and exploration, making it an ideal destination for a delightful getaway.

Shopping

In Winchester, you can enjoy shopping at Burlington Mall, just 2.5km away, offering a vibrant mix of businesses and family entertainment. Harvard Square and Boston Public Market, both within 6-4.3km, provide a lively city atmosphere for unique gifts, perfect for a memorable shopping experience.

Recreation

Agganis Arena offers an energetic atmosphere with various sports events, perfect for those seeking excitement. The House of Blues Boston and Hatch Shell provide vibrant music experiences, allowing you to unwind and enjoy live performances in a lively setting, just a short distance from Winchester.

Adventure

Horn Pond, located 1.2km from Winchester, offers a tranquil outdoor experience, perfect for leisurely walks and picnics. The Courageous Sailing Center, 4.3km away, provides thrilling water sports adventures. For scenic hiking, explore the Irish Heritage Trail, situated 5.0km from Winchester, showcasing beautiful landscapes.

Nightlife

In Winchester, the LEGOLAND® Discovery Center provides a fun-filled arcadeAdventureZone perfect for families. For a cultural evening, the Somerville Theatre offers a blend of entertainment and romance. Enjoy a relaxed drink at Cambridge Common, an inviting pub ideal for lively conversation and a romantic atmosphere.

Booking tips and Expedia advantages for Winchester

For a budget-friendly visit to Winchester, Massachusetts, consider travelling during the off-peak months of December to February, when accommodation prices are lower. Sundays tend to be the least expensive days to stay, while Saturdays are pricier. Use Expedia's search tool to sort options by budget and package deals that combine hotels, flights, and activities for additional savings. Look for hotel deals and minute offers to maximise your budget. Don't forget to explore free local attractions to enrich 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 budget, preferred location, and desired hotel type. To discover the most affordable options and offers, arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package.

Find the best attractions near Winchester

Winchester, Massachusetts, is an ideal destination for outdoor enthusiasts and culture seekers alike, offering a family-friendly atmosphere. Visitors can explore notable attractions such as the Winchester Discovery Centre, Winchester Cathedral, and the historic Winchester Castle, along with the Great Hall. These sites provide a rich blend of history and urban parks, ensuring a fulfilling experience for travellers looking to immerse themselves in local culture and heritage.

• Fenway Park: Experience the rich history and vibrant atmosphere of one of America’s oldest ballparks, home to the Boston Red Sox. Enjoy a game or take a guided tour to learn about its iconic features and the passionate sports culture surrounding it.
• Harvard University: Visit the world-renowned institution, steeped in tradition and academic excellence. Stroll through its picturesque campus, admire historic buildings, and soak up the intellectual culture that has shaped many leaders.
• TD Garden: Discover this premier venue that hosts major sporting events and concerts, offering a dynamic atmosphere. Whether attending a game or a concert, you'll feel the energy of Boston's business and entertainment scene.

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

For your visit to Winchester, Massachusetts, the primary airport is Boston Logan International Airport (BOS), situated 5.6km away. Nearby excellent hotels include the 5-star Encore Boston Harbor, 1.9km from the airport, and both The Langham and Boston Harbor Hotel, each 1.2km from BOS. Another option is Providence T.F. Green Airport (PVD), located 51.9km away, with the Omni Providence Hotel, Renaissance Providence Downtown Hotel, and Graduate by Hilton Providence, all approximately 4.3km from the airport. Additionally, Manchester-Boston Regional Airport (MHT) is 22.4km away, with hotels like The Grand at Bedford Village Inn and DoubleTree by Hilton Manchester Downtown, both 2.5km from MHT.