Winchester vacation rentals

We found 664 vacation rentals — enter your dates for availability

Discover a selection of 35 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.

Vacation rentals with weekly discounts - Winchester

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Find out more about Winchester

Find out more about Winchester

Why visit Winchester

  1. Historic Attractions: Explore Winchester’s rich history through its stunning castles and ancient streets.
  2. Beautiful Countryside: Venture into the picturesque Hampshire countryside for breathtaking views and outdoor activities.
  3. Vibrant City Atmosphere: Enjoy the charm of central Winchester, filled with friendly locals and a lively ambiance.
  4. Cultural Experiences: Immerse yourself in the cultural offerings, including the renowned university and local events.
  5. Diverse Accommodation: Choose from cozy apartments, charming cottages, or modern hotels to enhance your stay.

Popular types of accommodation in Winchester

If you're searching for the perfect vacation rental in Winchester, look no further! Our most popular accommodations include charming apartments, convenient apart hotels, and cozy cottages. Whether you're interested in bungalows, spacious flats, or inviting houses, we have a variety of options to suit your needs. Enjoy your stay in Winchester with transparency and savings, knowing you have the best selection at your fingertips.

  • Apartments: The top choice for visitors in Winchester, offering modern comforts and convenient locations for exploring the city.
  • Cottages: A charming option that provides a cozy and traditional atmosphere, perfect for a relaxing getaway.
  • Caravan Parks: A unique and affordable lodging choice, ideal for those seeking a fun outdoor experience.
  • Houses: Great for groups or families, these homes offer space and privacy for your stay.
  • Cabins: A delightful retreat for nature enthusiasts, providing a rustic experience close to the great outdoors.**

Top attractions in Winchester

Winchester, England, offers a perfect blend of outdoor adventure and scenic beauty, making it an ideal vacation spot. Visitors can explore captivating attractions like historic castles, the beautiful countryside, and the renowned university. Whether you seek cultural experiences, beach outings, or outdoor activities, Winchester has something for everyone, ensuring a memorable trip filled with exploration and enjoyment.

  1. Winchester Cathedral: A magnificent example of Gothic architecture, Winchester Cathedral boasts stunning stained glass windows and rich history. Explore its beautiful interiors and learn about its significance in English culture.
  2. Paultons Family Theme Park - Home of Peppa Pig World: This vibrant theme park, located 13 miles from Winchester, offers fun rides and attractions themed around Peppa Pig, providing an exciting experience for families and young children.
  3. University of Winchester: A historic institution with picturesque grounds, the University of Winchester features beautiful architecture and a rich cultural atmosphere, perfect for leisurely strolls and exploring its heritage.

Things to do recommended for couples

Looking for a romantic getaway in Winchester? Explore the charming Wickham Estate and Raimes English Sparkling wineries for delightful tastings. For an adventurous twist, hit the slopes at Alpine Snowsports Southampton. Enjoy the perfect blend of relaxation and excitement together!

Things to do recommended for families

Explore the wonders of the Winchester Science Centre and Planetarium for a fun, educational experience. Enjoy a thrilling cricket match at the Ageas Bowl, just 9 miles away, or unwind at Farley Mount Country Park, only 3 miles from Winchester, perfect for family relaxation and outdoor activities.

Things to do recommended for groups

Experience the vibrant culture at Theatre Royal Winchester, shop at the WestQuay Shopping Centre for unique finds, and enjoy a romantic tour at the Bombay Sapphire Distillery. These activities offer a perfect blend of entertainment and local charm for your group vacation.

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

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your preferences during your search. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winchester with a group: Think about how many bedrooms you'll require and any additional features you might want, like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Winchester with young kids: Traveling with young kids can be quite demanding. It's important to prioritize 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 families, a vacation isn't truly satisfying without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer amenities like feeding bowls and beds, ensuring that everyone feels comfortable and at ease.
  • 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 utilizing the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Winchester

Winchester, England, offers an unforgettable travel experience filled with rich history and stunning scenery. Explore the charming central Winchester, where friendly locals welcome you to its vibrant atmosphere. Venture into the picturesque Hampshire countryside for breathtaking views and family-friendly excursions. Whether you're wandering through the historic streets or enjoying relaxing moments in the heart of Winchester, this destination promises a delightful blend of adventure and tranquility for every traveler.

  • Southampton: Located approximately 12 miles from Winchester, Southampton is a vibrant city known for its beautiful waterfront and rich maritime history. Visitors can enjoy outdoor adventures at the nearby national parks or relax at the marina. The city offers a lively shopping experience with its mall centers and an array of entertainment options, including theaters showcasing various performances. Don’t miss the opportunity to explore the stunning coastline and indulge in outdoor activities like sailing and cycling. Southampton is a perfect blend of urban excitement and natural beauty.
  • Eastleigh: Just 7 miles from Winchester, Eastleigh is a charming city that appeals to families and adventure seekers alike. With its extensive recreational areas, visitors can enjoy outdoor activities that cater to all ages. The local theater scene provides cultural enrichment, while the nearby theme park offers thrill rides for those looking for excitement. Eastleigh's close proximity to national parks makes it a great spot for hiking and nature walks, making it an ideal destination for those seeking both relaxation and adventure.
  • Kings Worthy: Situated right in the vicinity of Winchester, Kings Worthy is a picturesque village that offers stunning scenery and outdoor activities. Known for its tranquil atmosphere, it’s perfect for those looking to unwind. Visitors can enjoy golf at local courses or catch a show at the local theater. The area is also close to national parks, providing ample opportunities for hiking and exploring the great outdoors. With its blend of natural beauty and recreational options, Kings Worthy is a peaceful retreat for any traveler.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January40.3°F (4.6°C)Light RainMostly CloudyAverageSlightly Low
February41.2°F (5.1°C)Light RainMostly CloudyAverageAverage
March43.9°F (6.6°C)Light RainMostly CloudyAverageAverage
April47.8°F (8.8°C)Light RainMostly CloudyAverageAverage
May53.2°F (11.8°C)Light RainMostly CloudySlightly LowSlightly High
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 LowSlightly Low
November46.8°F (8.2°C)Light RainMostly CloudySlightly HighSlightly Low
December43.0°F (6.1°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Are you aiming to save on your next getaway? It might be beneficial to keep your travel dates flexible, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash™ on your reservation. Being the planner really pays off! When you join our travel rewards program, One Key, you can immediately access exclusive member savings and earn OneKeyCash™ on qualifying bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers an easy way to plan your travels, allowing you to start new trips, continue from where you last left off, or manage your existing plans. You'll see your saved or booked properties neatly organized under Potential, Upcoming, or Current Trips. To begin utilizing Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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)
  • New Forest Wildlife Park (14.5 mi / 23.4 km)
  • Thruxton Motorsport Centre (16.3 mi / 26.3 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)
  • Meon Shore Beach (16.9 mi / 27.2 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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