Find hotels in Winchester, MA from Rp1.430.527

Top reasons to visit Winchester

• Outdoor Adventures: Winchester offers a range of family-friendly outdoor activities, perfect for those seeking adventure.
• Cultural Attractions: Explore art galleries and significant historic sites that provide a rich cultural experience.
• Charming Streets: Wander through Central Winchester’s picturesque streets, filled with friendly locals and inviting cafes.
• Proximity to Boston: Enjoy easy access to the historic Beacon Hill and the vibrant heart of Boston for enriching experiences.
• Diverse Accommodations: Choose from welcoming bed and breakfasts to versatile hotels catering to various needs and budgets.

Find great hotels near Winchester

Discover a variety of accommodation options in Winchester, Massachusetts, ranging from welcoming bed and breakfasts to versatile hotels suited for business travellers. Many establishments offer pet-friendly services and embrace an LGBTQIA-friendly atmosphere, ensuring a comfortable stay for all. With a focus on affordable lodgings, you can find budget-friendly rates without sacrificing quality, making it easy to enjoy your visit to this charming town.

• Hyatt Regency Boston/Cambridge: This 4-star hotel offers a sophisticated atmosphere perfect for business travellers and LGBTQIA guests. Located 11.3km from Winchester, the Hyatt Regency Boston/Cambridge features modern amenities and a welcoming environment. Guests can take advantage of its pet-friendly policy, allowing dogs on-site alongside service animals. With a variety of services tailored to LGBTQI travellers, this hotel also boasts a range of business facilities, ensuring a seamless stay for those combining work with leisure.
• Wyndham Boston Beacon Hill: Situated 11.3km from Winchester, the Wyndham Boston Beacon Hill is a 3.5-star hotel known for its charming yet contemporary flair. Ideal for business trips and pet-friendly stays, this property welcomes dogs and provides essential amenities for furry companions. With its convenient location near Boston's historic Beacon Hill neighbourhood, guests enjoy easy access to local attractions, making it a delightful choice for both work and exploration.
• Studio Allston Hotel: Located just 9.7km from Winchester, the eco-certified Studio Allston Hotel is a unique retreat for environmentally conscious travellers. This 3.5-star hotel features a modern design and offers a range of amenities for business and pet-friendly stays. The property’s commitment to sustainability appeals to eco-friendly guests, while its welcoming atmosphere ensures a comfortable experience. With pets permitted and service animals accommodated without fees, Studio Allston is perfect for those looking to blend business with a touch of nature.

Where to stay in Winchester

Winchester, Massachusetts, offers a delightful blend of family-friendly charm and urban sophistication. Explore the picturesque streets of Central Winchester, where you'll find friendly locals and inviting cafes. Just a short journey away, the historic Beacon Hill and the vibrant heart of Boston promise enriching experiences. Whether you seek a calmer vacation or a bustling city atmosphere, Winchester and its nearby attractions cater perfectly to your desires.

• Boston: As a vibrant metropolis, Boston is a cultural and historical hub that offers a plethora of experiences for travellers. Situated conveniently near Winchester, it boasts a diverse range of attractions, from renowned educational institutions to lively music venues. Visitors flock to Boston year-round, particularly in the summer months and during the autumn foliage in October. The city's historic sports stadiums and iconic colleges provide a unique glimpse into America’s rich heritage. Be sure to explore lively shopping districts and sample local cuisine in its many restaurants, making your visit both educational and enjoyable.
• Cambridge: Located a mere 9.7km from Winchester, Cambridge is a city that perfectly marries intellect with charm. Known for its prestigious universities, the area attracts families and business travellers alike throughout the year. The peak seasons in April and July bring visitors eager to explore its vibrant shopping centres and engage in educational pursuits. Cambridge’s historic architecture and lively atmosphere create an inspiring backdrop for leisurely strolls or family outings. Don’t miss the opportunity to visit local landmarks, including event venues and sports facilities that enrich this dynamic city experience.
• Woburn: Just 3.2km from Winchester, Woburn is a delightful city that offers a welcoming atmosphere for visitors. The city sees steady traveller arrivals throughout the year, with peaks in spring and summer. Woburn is perfect for families and business travellers seeking a blend of city life and suburban tranquillity. The local shopping centres provide ample opportunities for retail therapy, while the historic sites and event venues add a unique flair to your visit. Enjoy a day exploring the parks or dining at local eateries, making Woburn a charming addition to your itinerary.

Things to do near Winchester

Winchester is an ideal destination for families seeking outdoor adventures and urban experiences. Visitors can explore art galleries, enjoy thrilling activities, and indulge in family outings. Shopping enthusiasts will appreciate the local shopping centres and malls, making it a well-rounded location for leisure and entertainment.

Shopping

The nearest shopping experience is at Harvard Square, just 9.7km away, offering a vibrant mix of shops and entertainment. Additionally, Boston Public Market, 11.3km from Winchester, features local produce and goods. If you're up for a drive, consider visiting the Harvard Cooperative Society, also 9.7km away.

Recreation

At Middlesex Fells Reservation, just 1.6km from Winchester, immerse yourself in nature with serene walking trails and picturesque landscapes, perfect for relaxation. For a lively experience, enjoy the energetic atmosphere at Agganis Arena, seven miles away, or catch a captivating performance at MGM Music Hall, eight miles from Winchester.

Adventure

Horn Pond, located 3.2km from Winchester, offers a picturesque outdoor experience with scenic walking trails and tranquil waters, perfect for leisurely strolls. For water sports enthusiasts, the Courageous Sailing Center, 11.3km away, provides exhilarating sailing adventures amid stunning views, while Boston Paintball, also 11.3km distant, promises thrilling action-packed fun.

Nightlife

In Winchester, the LEGOLAND® Discovery Center offers an adventurous arcade experience just 8.0km away. The Somerville Theatre, 6.4km distant, provides a romantic atmosphere rich in culture, while Cambridge Common, also 8.0km away, is a lively pub perfect for enjoying drinks and entertainment.

Booking tips and Expedia advantages for Winchester

To save money on your trip to Winchester, consider visiting during the cheaper months of December to February, as hotel prices are generally lower. Sunday is the most affordable day for accommodation, while Saturday tends to be pricier. Use Expedia's search tool to filter options by budget and hotel type, such as eco-certified properties. Additionally, consider booking a package deal that combines flights, hotels, and activities for further savings. Take advantage of free activities in the area to enhance 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: Expedia's search tool enables you to specify your budget, preferred location, and additional criteria. You can organise your search results to display prices from lowest to highest, allowing you to find the most affordable hotels first. Furthermore, you have the option to refine your selections by hotel type; for instance, by selecting the Eco-certified filter, you will be presented with sustainable and environmentally friendly hotels that are available for booking.
• Consider bundling your trip: You can save money by combining your hotel reservation in Winchester with your flights and activities through an Expedia package deal.

Find the best attractions near Winchester

Winchester offers a delightful blend of family-friendly and outdoor activities, making it an ideal destination for city-themed vacations. Visitors can explore a variety of attractions, including urban parks, historic colleges and universities, and significant historic sites. These points of interest provide a rich cultural experience, perfect for those seeking to immerse themselves in the local heritage while enjoying a vibrant city atmosphere.

• Fenway Park: Experience the thrill of America's pastime at Fenway Park, a historic sports stadium steeped in tradition. Located 12.9km from Winchester, this iconic venue not only offers exhilarating baseball games but also showcases a vibrant culture with its rich history and passionate fans.
• Harvard University: Just 9.7km away, Harvard University invites you to explore its prestigious campus, where history and intellect converge. Stroll through its beautiful grounds, visit renowned museums, and soak up the academic atmosphere that has shaped so many leaders.
• TD Garden: Situated 11.3km from Winchester, TD Garden serves as a dynamic event venue. Whether attending a sports event or a concert, the energy and business vibes here create an unforgettable experience in the heart of Boston.

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, the nearest major airport is BOSton Logan International Airport (BOS), situated 14.5km away. Nearby, you can find several exquisite hotels, such as the InterContinental Boston, 3.2km from the airport, and The Langham, Boston, also 3.2km away. Both offer convenient access to Logan via local transport services. If you prefer to fly into Providence, T.F. Green Airport (PVD) is 85.3km from Winchester, with options like the Omni Providence Hotel, located 11.3km from the airport. Alternatively, Manchester-Boston Regional Airport (MHT) is 57.9km away, with hotels like Four Points by Sheraton just 3.2km from there.