Winchester holiday lettings

Why visit Winchester

• Historic Sites: Discover the rich history at the stunning Winchester Cathedral and other local landmarks.
• Charming Centre: Stroll through Winchester Centre, offering delightful shops and eateries.
• Outdoor Activities: Enjoy various outdoor pursuits in the picturesque parks and spaces around the town.
• Farmers Market: Experience the Winchester Farmers Market for fresh produce and local delicacies.
• Proximity to Boston: Take advantage of nearby Boston's vibrant urban culture and historical attractions.

Popular types of accommodation in Winchester

If you're considering a getaway to Winchester, you're in for a treat. Our most sought-after vacation rentals include Houses, Apartments, and Condos, offering a variety of choices to suit your needs. With convenient access to local attractions, including the historic Century Winchester and the First Winchester Hospital, you can enjoy your stay with ease. Plus, many of our rentals provide room service for added comfort and convenience.

• Houses: The top choice for visitors in Winchester, offering spacious and comfortable stays for families or groups seeking a homely atmosphere.
• Apartments: A popular selection for those desiring a convenient and stylish base, ideal for couples or solo travellers.
• Condos: A well-liked option featuring modern amenities, perfect for guests looking for a bit more luxury during their stay.
• Cottages: Charming and cosy, these rentals provide a quaint escape for those wanting a rustic experience.
• House Boats: An unusual yet delightful choice for adventurous travellers, offering a unique way to enjoy the water.**

Top attractions near Winchester

Winchester, Massachusetts, offers a delightful blend of outdoor activities, cultural experiences, and family-friendly attractions. Visitors can explore historic sites, vibrant urban parks, and local universities. Highlights include the Winchester Farmers Market and the stunning Winchester Cathedral. Whether you're seeking leisurely strolls or engaging family outings, Winchester is an ideal destination for a memorable holiday.

• Fenway Park: A historic sports stadium famed for its iconic Green Monster, Fenway Park offers an electric atmosphere for baseball fans and a glimpse into American sports culture.
• Harvard University: This prestigious historic college boasts stunning architecture and rich history, providing visitors with an inspiring cultural experience in one of the world's leading educational institutions.
• TD Garden: A bustling event venue, TD Garden hosts a variety of concerts and sports events, embodying a vibrant business vibe and a hub for entertainment enthusiasts.

Things to do recommended for couples

For a romantic getaway in Winchester, explore the lively House of Blues for a concert, indulge in a meal at the charming Russell House, or enjoy a captivating performance at the Jose Mateo Ballet Theatre. Each venue offers a unique atmosphere perfect for couples.

Things to do recommended for families

Families will have a fantastic time at LEGOLAND® Discovery Center, just 3.1km away, filled with fun activities. For sports enthusiasts, Agganis Arena, 4.3km distant, offers thrilling events. Enjoy nature at Middlesex Fells Reservation, a mile from Winchester, perfect for relaxation and wellness.

Things to do recommended for groups

Groups visiting Winchester can enjoy a day out at Harvard Square for shopping and entertainment, catch a show at Somerville Theatre for a cultural experience, or relax in the natural beauty of Horn Pond, perfect for outdoor activities and family fun.

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay frequently results in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Where to stay near Winchester

Winchester, Massachusetts, is a charming destination perfect for family-friendly adventures and cultural explorations. Visitors can enjoy the picturesque Winchester Centre, with its quaint shops and eateries, before venturing into the bustling urban vibes of nearby downtown Boston. The Greater Boston area offers a rich historical backdrop, ensuring a delightful experience for all who visit this lovely part of the United States.

• Boston: Boston, a bustling metropolis located 5.0km from Winchester, is a rich tapestry of history and modernity. Known for its vibrant city life, it offers a myriad of cultural experiences, making it a fantastic destination for families and solo travellers alike. Here, you can immerse yourself in world-class educational institutions, attend music concerts, and indulge in shopping at numerous mall centres. The city is home to iconic landmarks such as historic sports stadiums and event conference venues, ensuring that there is always something exciting happening. A stroll along the picturesque Freedom Trail reveals the city's pivotal role in American history, while the dynamic atmosphere of its diverse neighbourhoods adds to the charm.
• Woburn: Just 1.2km from Winchester, Woburn is a welcoming city that combines a sense of community with urban amenities. Perfect for families seeking a city-themed experience, Woburn boasts a variety of shopping centres and educational opportunities. The city is also known for its recreational spaces, including a local beach and stadiums for sports enthusiasts. Woburn’s blend of suburban charm and city life makes it an ideal stop for those looking to relax while still enjoying cultural attractions. The event conference venues frequently host community events, adding to the vibrant local atmosphere.
• Cambridge: Located 3.7km from Winchester, Cambridge is renowned for its prestigious universities and rich cultural heritage. Visitors flock to this city for its vibrant atmosphere, combining educational pursuits with family-friendly activities. Shopping centres and a variety of dining options abound, catering to every taste. The presence of historic college campuses offers a unique backdrop for leisurely exploration, while local stadiums host a variety of sporting events. Cambridge's historic sports stadiums and cultural landmarks create an engaging environment for all who visit, making it a must-see on your itinerary.

Best time to go to Winchester

If you're planning a trip to Winchester, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like February and November to December tend to have fewer bookings and better deals.

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	Slightly Low
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	Average
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	Slightly High
August	72.3°F (22.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	65.3°F (18.5°C)	Light Rain	Mostly Sunny	Slightly High	Average
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	Average

What do I need to keep in mind when booking a vacation in 'Winchester

If you're travelling with a group, as a family, bringing your pets along, or seeking extended stays, it's important to filter according to your key priorities. Here are some helpful booking tips for using Vrbo.

• Traveling to Winchester with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor area for group gatherings. Thankfully, you can easily apply filters for all these options and more on Vrbo.
• Traveling to Winchester with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
• Taking your pets with you to Winchester: For many, a family holiday isn't finished without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
• Planning for a long term stay visiting Winchester: If you're seeking holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy platform for planning your journeys, allowing you to start new trips, continue from where you last stopped, or easily view and manage your arrangements. You can find any properties you’ve saved or booked sorted into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.