Winchester vacation rentals

We found 262 vacation rentals — enter your dates for availability

Discover a selection of 40 homes, 39 apartments, and other vacation rentals in Winchester that are perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the amenities you expect for your stay, which might include cable TV and a washer and dryer. No matter what you're looking for, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

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Find out more about Winchester

Why visit Winchester

  • Rich history: Winchester is steeped in history, featuring historic colleges, museums, and houses that cater to culture enthusiasts.
  • Stunning scenery: The Greater Winchester area offers picturesque landscapes, perfect for outdoor and adventure seekers.
  • Charming downtown: Explore the inviting historic downtown filled with unique shops and cafes.
  • Cozy accommodations: Enjoy a stay in delightful holiday cottages or spacious vacation rentals tailored to your needs.
  • Welcoming locals: Experience the warmth and friendliness of the residents, enhancing your visit to this charming city.

Popular types of accommodation in Winchester

Vrbo offers a variety of vacation rentals in Winchester, perfect for every type of traveler. Whether you’re looking for cozy cottages, spacious houses, or comfortable apartments, you’ll find the ideal accommodation to suit your needs. Popular choices include charming cottages in Winchester and inviting house rentals, ensuring you have a memorable stay. Explore your options and discover the perfect rental for your getaway.

  • Apartments: The top choice for visitors in Winchester, offering modern amenities and convenient locations for a comfortable stay.
  • Houses: A great option for families or groups, providing a home-like atmosphere with ample space and privacy.
  • Cottages: Quaint and charming, these cozy retreats are perfect for experiencing the idyllic English countryside.
  • Caravan Parks: A unique lodging choice, ideal for those looking to enjoy outdoor adventures while still having access to facilities.
  • Cabins: A popular option for nature lovers, offering rustic charm and a peaceful setting away from the hustle and bustle.**

Top attractions in and around Winchester

Winchester, England is perfect for outdoor and adventure seekers, boasting stunning scenery and rich history. Explore notable attractions such as historic colleges, museums, and historic houses that cater to culture enthusiasts and families alike. Whether you're traveling solo, with family, or friends, you'll find plenty of exciting activities and experiences to make your visit unforgettable.

  • Winchester Cathedral: A stunning example of Gothic architecture, Winchester Cathedral boasts impressive stained glass windows and a rich history dating back over a thousand years. Visitors can enjoy serene walks through its beautiful grounds and learn about its significance in English heritage.
  • Paultons Family Theme Park - Home of Peppa Pig World: Located 13 miles from Winchester, this family-friendly theme park features thrilling rides and attractions themed around Peppa Pig. It's a delightful destination for families, offering entertainment and fun for visitors of all ages.
  • University of Winchester: This historic university, situated in the heart of Winchester, provides a picturesque campus with beautiful architecture. It's known for its vibrant community and cultural events, making it a great spot to explore local student life and history.

Things to do recommended for couples

For a romantic getaway in Winchester, explore the enchanting Wickham Estate and savor delightful wines, or visit Raimes English Sparkling for a charming tasting experience. For something unique, try Alpine Snowsports Southampton for a fun day on the slopes, combining adventure with romance.

Things to do recommended for families

Your family will have a blast at the Winchester Science Centre and Planetarium, explore sports events at St. Mary's Stadium just 11 miles away, and unwind at Farley Mount Country Park, a relaxing retreat only 3 miles from the city center.

Things to do recommended for groups

Your group can enjoy shopping and entertainment at WestQuay Shopping Centre, explore the romantic Bombay Sapphire Distillery, or hit the links at Romsey Golf Club for some outdoor sports fun—all within a short drive from Winchester.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When planning your trip—whether you're traveling with a group, with family, bringing pets, or seeking extended stays—be sure to apply the appropriate filters to match your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Winchester with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group activities. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Winchester with young kids: Traveling with young kids can present some challenges. It's important to prioritize their comfort and safety, along with amenities suitable for their age, like a private pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Winchester: For many families, a vacation wouldn't feel complete without their beloved pet. If you can relate, take a look at Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that all members of your family feel comfortable and at home.
  • Planning for a long term stay visiting Winchester: If you’re in search of vacation rentals that offer discounts 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 consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in and around Winchester

Winchester, England, offers a captivating blend of history and natural beauty, perfect for outdoor enthusiasts and those seeking adventure. Explore the charming historic downtown, enjoy cozy accommodations in holiday cottages, and take in the picturesque scenery of the Greater Winchester area. Nearby, indulge in the delightful wine country and experience the warmth of friendly locals. Whether you're on a family trip or a relaxing getaway, Winchester has something for everyone.

  • Southampton: Southampton is a vibrant city located 12 miles from Winchester, known for its dynamic blend of outdoor adventures and urban experiences. Visitors can explore the bustling shopping mall center, catch a performance at the local theater, or indulge in educational visits at various institutions. The city is home to stunning attractions such as the picturesque marina and the nearby national park, offering ample opportunities for hiking and enjoying nature. With its lively atmosphere and access to beaches, Southampton is perfect for those seeking an adventurous getaway.
  • Eastleigh: Situated just 7 miles from Winchester, Eastleigh is a family-friendly city that invites travelers to embrace the outdoors while enjoying recreational activities. The area boasts a variety of venues, including theaters and educational facilities, making it ideal for family outings. Eastleigh is also home to a delightful theme park and a national park, providing perfect spots for adventure and relaxation. Visitors can enjoy exploring the scenic parks and engaging in community events, ensuring a fun-filled experience for all ages.
  • Sutton Scotney: Nestled close to Winchester, Sutton Scotney is a charming village that offers a delightful cultural experience. With its family-oriented environment, visitors can enjoy a variety of entertainment options including a shopping center and an arena entertainment facility. The village is in proximity to several local landmarks such as sports facilities and a theme park, making it an ideal destination for fun-filled family days. Sutton Scotney combines a quaint village atmosphere with engaging activities, perfect for creating lasting memories.

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 July, September and November, while off-peak times, like May, October and December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.3°F (4.6°C)Light RainMostly CloudyAverageSlightly Low
February41.2°F (5.1°C)Light RainMostly CloudyAverageSlightly Low
March43.9°F (6.6°C)Light RainMostly CloudyAverageSlightly Low
April47.8°F (8.8°C)Light RainMostly CloudyAverageAverage
May53.2°F (11.8°C)Light RainMostly CloudySlightly LowAverage
June59.2°F (15.1°C)Light RainMostly CloudyAverageAverage
July62.8°F (17.1°C)Light RainMostly CloudySlightly HighSlightly High
August62.1°F (16.7°C)Light RainMostly CloudyAverageSlightly High
September58.6°F (14.8°C)Light RainMostly SunnySlightly HighAverage
October53.4°F (11.9°C)Light RainMostly CloudySlightly LowAverage
November46.8°F (8.2°C)Light RainMostly CloudySlightly HighAverage
December43.0°F (6.1°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a difference since prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect place for your trip.

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you'll receive OneKeyCash on the full booking amount. Being the organizer has its benefits. Enroll in our One Key rewards program to unlock exclusive member discounts and earn OneKeyCash on qualifying stays. Sign up today and begin accumulating your rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board is designed to help you plan your travels seamlessly. You can create new trips, manage your ongoing plans, and keep track of your bookings all in one convenient place. Your saved or booked properties are neatly organized into categories: Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Historic Winchester will entice you

Take a vacation to Winchester and enjoy the area's cathedral, history and museums. Well known for its gardens, monuments and shopping, this welcoming city won't disappoint. Southampton Cruise Terminal and New Forest National Park are just a couple of the must-sees in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Winchester

Do you want to find attractions to visit during your stay? Venture out of your cozy vacation rental and experience everything that Winchester has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Marwell Zoo (4.8 mi / 7.7 km)
  • Broadlands Estate (9.5 mi / 15.3 km)
  • The Common (10 mi / 16.1 km)
  • Paultons Family Theme Park - Home of Peppa Pig World (13 mi / 21 km)
  • Thruxton Kart Centre (16.3 mi / 26.3 km)
  • Basingstoke Leisure Park (16.4 mi / 26.4 km)

Exploring the gardens and other natural features in Winchester

Whether you're an outdoor enthusiast or just want to take in the scenery, Winchester is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • New Forest National Park (19.6 mi / 31.5 km)
  • Avington Park (3.3 mi / 5.3 km)
  • Mayflower Park (12 mi / 19.3 km)
  • Hawk Conservancy Trust (14.9 mi / 24 km)
  • Calshot Beach (16.9 mi / 27.1 km)
  • Lee-on-the-Solent Beach (18 mi / 28.9 km)

Transportation to and around Winchester

The nearest airport is in Southampton (SOU), located 7.9 mi (12.6 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Farnborough (FAB), which is 27.7 mi (44.6 km) away.

If you prefer to travel by train, Winchester Station, Winchester Shawford Station and Winchester Micheldever Station are the main stations in the city.

Frequently asked questions

What is the best area to stay in Winchester when booking a vacation rental?
When planning a vacation in Winchester, England, one of the best areas to consider for your rental is the historic city center. This vibrant neighborhood is steeped in history and offers a lot of attractions right at your doorstep. You can easily visit the magnificent Winchester Cathedral, an architectural marvel that dates back to the 11th century and features stunning stained glass and beautiful gardens. Just a short stroll away, you'll find the Great Hall, known for its iconic round table associated with the legend of King Arthur. The city center is also home to charming shops, cafes, and restaurants, making it a delightful place to explore.

Another fantastic area is the suburb of Hyde, which is slightly quieter yet still within a short walk from the city center. This neighborhood boasts lovely parks and residential charm, superb for families or those looking for a peaceful retreat after a day of sightseeing. The nearby Winchester Science Centre and Planetarium offers a great experience for visitors of all ages, providing interactive exhibits and shows that spark curiosity about the universe.

If you prefer a more rural setting, the area surrounding the South Downs National Park offers stunning natural beauty and scenic walking trails. Staying here gives you access to the picturesque countryside while still being just a short drive from the city's attractions. Overall, Winchester has a variety of properties available, particularly in the city center where you can find numerous vacation rentals that cater to different preferences and budgets.
How much does it cost to rent a vacation home in Winchester?
Prices for vacation rentals in Winchester vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winchester to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winchester vacation house rentals?
You can find great discounts on house rentals in Winchester on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Winchester?
For renting a beach house in Winchester, England, travelers should look toward the nearby coastal areas, particularly along the Solent, which includes charming seaside towns like Southsea and Hayling Island. Southsea, located just a short drive from Winchester, offers a vibrant beachfront atmosphere with a mix of Victorian architecture and modern amenities. Here, visitors can find beach houses featuring spacious terraces, sea views, and easy access to the pebbled beach, ideal for sunbathing and seaside strolls. Many properties in this area come equipped with outdoor seating areas, barbecue facilities, and family-friendly amenities, making them suitable for gatherings and relaxation.

Hayling Island, further along the coast, is another excellent option, known for its sandy beaches and water sports activities. Rentals here often include modern kitchens, private gardens, and proximity to local attractions such as the Hayling Island Funfair and the nature reserves that provide opportunities for walking and cycling.
What is the most popular type of vacation rental accomodation in Winchester?
In Winchester, vacation houses are the most popular rental option, with about 31 available throughout the city. These properties often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups. Many of these houses are located in charming neighborhoods close to historic sites like the Winchester Cathedral and the Great Hall, providing easy access to local attractions. Additionally, there are approximately 26 apartments available, which offer a more compact living space with similar amenities, along with the convenience of being situated near shops and restaurants. Cottages, numbering around 21, provide a quaint and cozy atmosphere, often with unique character and access to outdoor spaces. For those seeking a more luxurious experience, several villas are also available, typically featuring upscale amenities such as private gardens and pools.
Are there any family house rentals in Winchester?
In Winchester, visitors can find a variety of family-friendly house rentals, with around 34 options available throughout the area. The neighborhoods surrounding the city center, such as Weeke and Badger Farm, offer charming homes that cater to families. Many of these properties feature spacious living rooms, fully equipped kitchens for preparing meals, and outdoor gardens where children can play.

Amenities like Wi-Fi and laundry facilities are commonly included, ensuring a comfortable stay for families. The locale is also brimming with history and culture; families can explore nearby attractions such as the Winchester Cathedral and the Great Hall, which houses the legendary Round Table.
Can I rent a vacation home with a pool or hot tub in Winchester?
In Winchester, there are several vacation homes available for rent that feature pools and hot tubs, providing a relaxing escape in this historic city. Visitors can find properties in charming neighborhoods that blend modern comforts with the city's rich heritage. Many of these homes offer amenities like private gardens, spacious outdoor areas for entertaining, and fully equipped kitchens for convenient meal preparations.
Can I find long-stay vacation rentals in Winchester?
A long-stay vacation rental in Winchester is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Winchester?
In Winchester, there are numerous pet-friendly house rentals available, with around 29 options to choose from. Many of these properties offer a variety of amenities tailored to enhance your stay, such as fully equipped kitchens, spacious living areas, and private gardens, which are great for pets to enjoy.

The city is rich in history and charm, and staying in a pet-friendly rental allows for easy exploration of the area. Nearby parks like Abbey Gardens and the picturesque River Itchen provide ample opportunities for outdoor walks and relaxation with your furry companions. Additionally, Winchester's quaint streets are lined with pet-friendly cafes and shops, making it convenient for travelers accompanied by pets to enjoy the local culture.
Are there any remote work vacation rentals in Winchester?
In Winchester, there are numerous remote work vacation rentals available, with around 61 options to choose from. This historic city offers a range of accommodations that cater to the needs of remote workers. Many properties feature dedicated workspaces, such as desks and comfortable chairs, ensuring a productive environment. High-speed Wi-Fi is commonly available, allowing for seamless connectivity for work-related tasks.

Travelers can expect amenities that enhance their stay, including well-equipped kitchens for preparing meals and comfortable living areas for relaxation after work hours. Some rentals may also provide additional features like laptop workspaces and safes for securing personal items.

Winchester itself is a charming city filled with cultural attractions, including the stunning Winchester Cathedral and the Great Hall, which famously houses King Arthur's Round Table. The local area offers lovely parks and gardens, superb for unwinding during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winchester vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winchester with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Winchester?
In Winchester, popular vacation rental amenities include WiFi, kitchens, and onsite parking, ensuring that travelers have the conveniences of home during their stay. Many rentals also feature coffee and tea makers, allowing guests to enjoy a warm beverage at their leisure. Additionally, patios are common, providing outdoor space for relaxation and enjoying the scenic surroundings of this historic city.
When is the best time to visit Winchester for a vacation rental?
September is widely regarded as the best time to visit Winchester for a vacation rental, as the summer crowds begin to thin while the weather remains pleasantly mild. The peak season, which runs from July to September, is characterized by vibrant outdoor activities and numerous events, making it a lively time to explore the city's rich history and stunning architecture.

During this peak period, visitors can enjoy comfortable temperatures ranging from the mid-50s to mid-70s Fahrenheit, ideal for strolling through the picturesque streets or visiting the iconic Winchester Cathedral. The city's charming parks and gardens provide ample opportunities for relaxation and picnicking, making it superb for families and couples alike.

If you're looking for a more budget-friendly experience, consider planning your visit in May. This month offers a beautiful spring atmosphere, with blooming flowers and fewer tourists, allowing for a more intimate exploration of Winchester's attractions, such as the Great Hall and the medieval streets of the city center.

Whichever time you choose to visit, Winchester's blend of historical charm and modern amenities ensures a memorable experience.
How early should I book a Winchester vacation rental?
Book your Winchester vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winchester?
In Winchester, visitors can explore a variety of historical and cultural attractions. The city's centerpiece is the magnificent Winchester Cathedral, known for its stunning architecture and historical significance. Nearby, the Great Hall houses the legendary Round Table of King Arthur, making it a must-see for history enthusiasts.

The charming streets of the Winchester city center, lined with shops and cafes, offer a delightful atmosphere for leisurely strolls. For those interested in nature, the picturesque River Itchen runs through the city, providing scenic walking paths and opportunities for riverside picnics.

The area around the University of Winchester also offers vibrant cultural experiences, with various events and exhibitions taking place throughout the year.
Can I change or cancel my Winchester home rental booking on Vrbo?
To find Winchester vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winchester vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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