Winchester Hotels from ₹7,681

Top reasons to visit Winchester

• Outdoor Activities: Winchester boasts beautiful urban parks and scenic countryside perfect for outdoor enthusiasts and families.
• Cultural Experiences: Explore historic colleges and significant sites that reflect the town's rich heritage.
• Charming Neighbourhoods: Experience the warmth of friendly locals in Winchester's delightful communities.
• Variety of Accommodations: Enjoy a range of lodging options from historic hotels to cosy bed and breakfasts, catering to all visitors.
• Proximity to Attractions: Visit nearby attractions like Bishops Waltham and British shingle beaches for a mix of history and natural beauty.

Find great hotels near Winchester

Discover the charm of Winchester, Massachusetts, with a variety of accommodation options tailored to suit every visitor. Whether you're seeking a historic hotel or a cosy bed and breakfast, you'll find pet-friendly and LGBTQIA welcoming establishments. Enjoy essential amenities such as accessible rooms and complimentary Wi-Fi, ensuring a comfortable stay for both business and leisure travellers alike. Experience the warm hospitality that Winchester has to offer during your holiday.

• citizenM Boston North Station: Located a mere 11.3km from Winchester, citizenM Boston North Station is a contemporary 4-star hotel perfect for business travellers seeking a vibrant and inclusive atmosphere. This property is not only LGBTQIA welcoming but also distinguished by its modern design and smart technology features. Guests can enjoy 24-hour access to the business centre and a co-working space, making it ideal for both work and relaxation. The hotel's commitment to LGBTQI travel guides ensures a supportive environment, making it a standout choice for diverse visitors.
• Hyatt Regency Boston/Cambridge: Also situated 11.3km from Winchester, the Hyatt Regency Boston/Cambridge is a 4-star hotel that combines business efficiency with a pet-friendly policy, making it an excellent option for travellers accompanied by their furry friends. This property welcomes LGBTQIA guests and features extensive conference space for meetings and events. With amenities catering to both business and leisure, including a welcoming atmosphere, this hotel is perfect for those looking to blend work with a little pleasure during their stay.
• Four Points by Sheraton Boston Newton: A little further afield at 11.3km from Winchester, the Four Points by Sheraton Boston Newton offers a nature-themed retreat infused with business-friendly features. This 3.5-star hotel is dedicated to creating a welcoming environment for LGBTQIA travellers and provides numerous amenities, including a 24-hour business centre and meeting rooms. Guests can unwind amidst nature while still enjoying easy access to business facilities, making it a well-rounded choice for both work and leisure activities.

Where to stay near Winchester

Winchester, Massachusetts, offers a delightful blend of outdoor adventures and cultural experiences, making it ideal for family vacations. Explore its charming neighbourhoods where friendly locals welcome you. Venture into the beautiful countryside, discover art and sports facilities, and enjoy the serene atmosphere. Nearby, you can visit Bishops Waltham and British shingle beaches, enhancing your travel experience with a mix of history and natural beauty. Experience the warmth of this vibrant community during your stay.

• Boston: Located 12.9km from Winchester, Boston is a vibrant city steeped in history and culture. As a major hub for education and the arts, it attracts a steady flow of visitors year-round, peaking from April to July. Here, you can experience a rich tapestry of family-friendly attractions, shopping centres, and world-class music concerts. Must-visit landmarks include historic sports stadiums and event venues that host a variety of activities. Boston offers a dynamic city experience where you can immerse yourself in its storied past while enjoying modern urban conveniences.
• Woburn: Just 3.2km from Winchester, Woburn is a charming city known for its family-friendly atmosphere and cultural experiences. Visitor numbers peak in the warmer months, particularly in April and July. Woburn boasts several shopping centres and educational venues, making it an excellent spot for families and casual explorers alike. Attractions include nearby beaches and stadiums, perfect for outdoor activities and community events. The city's welcoming vibe and convenient location make it an ideal place to unwind and enjoy local flavour.
• West Medford: Situated 3.2km from Winchester, West Medford is a delightful neighbourhood that offers a blend of culture and outdoor experiences. Its popularity peaks in spring and late autumn, making it a lovely spot for seasonal visitors. Known for its educational institutions and shopping areas, this neighbourhood is perfect for those looking to explore local history. Highlights include historic buildings and modern colleges that add to its charm. West Medford's scenic surroundings offer a peaceful retreat while still being close to bustling city life.

Things to do near Winchester

Winchester, Massachusetts, is an ideal destination for outdoor enthusiasts and families seeking cultural experiences. Visitors can engage in educational activities, explore local shopping centres, or enjoy winter sports at nearby ski fields. With its charming atmosphere and variety of attractions, Winchester promises a delightful vacation filled with memorable experiences.

Shopping

In Winchester, you can visit Wine & Cheese Cask, offering a delightful selection of gourmet items, just 8.0km away. Harvard Square, 9.7km from Winchester, boasts a vibrant atmosphere with shops and entertainment. If you're up for a drive, the Boston Public Market is 11.3km away, featuring local produce and goods.

Recreation

Middlesex Fells Reservation, only 1.6km from Winchester, offers a tranquil oasis for relaxation and wellness amidst nature, featuring scenic walking trails and serene landscapes. For entertainment, the MGM Music Hall at Fenway, 12.9km away, presents vibrant music concerts, while Agganis Arena, 11.3km distant, hosts spirited sports events.

Adventure

Horn Pond, located 3.2km from Winchester, offers a tranquil outdoor experience with scenic views and walking trails. For water sports enthusiasts, the Courageous Sailing Center, 11.3km away, provides thrilling sailing adventures. Boston Paintball, also 11.3km from Winchester, promises an exhilarating day of competitive fun.

Nightlife

Experience the vibrant nightlife at LEGOLAND® Discovery Center, an arcadeAdventureZone with thrilling vibes, only 8.0km from Winchester. For a cultural evening, visit Somerville Theatre, 6.4km away, offering romance and entertainment. Alternatively, unwind at Cambridge Common, a delightful drinking pub, also 8.0km distant, perfect for a romantic night out.

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 are generally the cheapest days to book a stay, while Saturdays tend to be pricier. Use Expedia's search tool to filter for budget-friendly hotels and eco-certified options. Additionally, look for package deals that combine flights, hotels, and activities for extra savings. Explore free local attractions and utilise the public transport system for affordable travel around the area.

• 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, desired location, and additional preferences. You can arrange your search results to display prices from lowest to highest, ensuring that you see the most affordable hotels first. Furthermore, you have the option to refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that are available for booking.
• Consider bundling your trip: You can potentially save money by combining your hotel reservation in Winchester with your flights and activities through an Expedia package.

Find the best attractions near Winchester

Winchester, Massachusetts, offers a delightful blend of outdoor activities and cultural experiences, making it ideal for family vacations. Visitors can explore urban parks, historic colleges and universities, and various significant sites that showcase the town's rich heritage. With attractions catering to those seeking cultural enrichment and family-friendly outings, Winchester promises an engaging and memorable experience for all travellers.

• Fenway Park: Experience the vibrant atmosphere of this historic sports stadium, renowned for its rich baseball heritage. Just 12.9km from Winchester, catch a game or take a guided tour to explore its storied past and iconic features, like the Green Monster.
• Harvard University: Located 9.7km away, this prestigious institution boasts stunning architecture and lush green spaces. Immerse yourself in the culture and history of one of the world’s leading universities, and consider joining a walking tour to learn about its illustrious alumni.
• TD Garden: Situated 11.3km from Winchester, this multi-purpose arena hosts a variety of events, from sports to concerts. Enjoy the buzzing atmosphere and consider attending a game or event to truly experience the local culture.

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, you can conveniently fly into Boston Logan International Airport (BOS), situated 14.5km away. Notable hotels nearby include the 5-star Encore Boston Harbor and The Langham, Boston, both approximately 3 and 3.2km from the airport, respectively. Another option is The Liberty, a Marriott Luxury Collection Hotel, located 4.8km away. Alternatively, you can consider Providence T.F. Green Airport (PVD), which is 54.8km from Winchester, with the Omni Providence Hotel and Graduate by Hilton Providence as excellent 4-star choices, both 11.3km from the airport. Manchester-Boston Regional Airport (MHT) is also an option, located 57.9km away, with nearby hotels like The Grand at Bedford Village Inn.