Winchester vacation rentals

We found 651 vacation rentals — enter your dates for availability

Discover a selection of 36 homes, 43 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.
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Find out more about Winchester

Find out more about Winchester

Why visit Winchester

  1. Rich history: Explore historic sites including colleges, museums, and charming houses that showcase Winchester's vibrant past.
  2. Scenic outdoor adventures: Enjoy beautiful landscapes and outdoor activities in the picturesque surroundings of Winchester.
  3. Welcoming locals: Experience the warmth of friendly locals who enhance your visit with their hospitality.
  4. Romantic getaways: Discover the ideal setting for romantic escapes, all within walking distance of top attractions.
  5. Diverse accommodation options: Choose from cozy vacation homes, charming cottages, and modern apartments for a comfortable stay.

Popular types of accommodation in Winchester

Planning a getaway to Winchester? Discover the charm of this picturesque destination with our diverse selection of vacation rentals. From cozy houses and charming cottages to modern apartments, you’ll find the perfect place to unwind. Explore our comprehensive listings for Winchester vacation rentals, holiday cottages, and more, ensuring a memorable stay filled with comfort and convenience. Your ideal home away from home is just a click away!

  • Houses: These are the top choice for visitors to Winchester, offering spacious and comfortable accommodations perfect for families or groups.
  • Apartments: A popular option for those seeking convenience, apartments provide a home-like atmosphere in the heart of the city.
  • Cottages: Quaint and picturesque, cottages offer a charming retreat for a cozy getaway.
  • Caravan Parks: Ideal for those who enjoy the outdoors, caravan parks provide a unique experience with facilities for camping and caravanning.
  • Cabins: These rustic lodgings are perfect for nature enthusiasts looking for a tranquil escape.**

Top attractions in Winchester

Winchester, England, is an ideal destination for those seeking outdoor adventures and scenic beauty. With a rich selection of historic sites including colleges, museums, and historic houses, the city offers a vibrant cultural experience. Whether traveling solo, with family, or as part of a group, visitors can enjoy a variety of attractions that cater to diverse interests and provide memorable experiences in this charming locale.

  1. Winchester Cathedral: A stunning example of Gothic architecture, this historic cathedral boasts intricate stonework and beautiful stained glass. Visitors can explore its rich history, attend services, and enjoy the serene atmosphere within.
  2. Paultons Family Theme Park - Home of Peppa Pig World: A delightful family-friendly theme park located 20.9km from Winchester, featuring rides and attractions based on the beloved Peppa Pig series. Perfect for families seeking fun and entertainment.
  3. University of Winchester: A historic institution with beautiful grounds, the university offers a glimpse into academic life and culture, making it a peaceful spot for a stroll or enjoying the architecture.

Things to do recommended for couples

Winchester offers delightful couple experiences! Explore the romantic vibes at Raimes English Sparkling, just 8.0km away, or enjoy a day at Wickham Estate, 17.7km out, for wine and entertainment. For an adventurous twist, hit the slopes at Alpine Snowsports Southampton, also 17.7km away.

Things to do recommended for families

Your family vacation in Winchester will be filled with excitement! Explore the wonders of the Winchester Science Centre and Planetarium, enjoy a cricket match at Ageas Bowl, and relax at The Common, perfect for outdoor fun and wellness activities. A delightful experience awaits!

Things to do recommended for groups

Explore the vibrant WestQuay Shopping Centre for a day of shopping and entertainment, catch a captivating performance at the Theatre Royal Winchester, or indulge in a tour at the Bombay Sapphire Distillery for a unique tasting experience—all perfect activities for your group adventure in Winchester.

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

If you're travelling with a group, family, pets, or planning an extended stay, be sure to prioritise your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winchester with a group: Think about how many bedrooms you require, as well as additional features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Winchester with young kids: Travelling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, as well as to seek out family-friendly amenities, like a private swimming pool. Additionally, you might want to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Winchester: For many families, a trip isn’t truly complete without their furry companions. If you can relate, consider exploring Vrbo properties 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 offering special rates 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 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 offers a delightful blend of history and charm, making it a perfect destination for outdoor and scenic adventures. Explore the historic downtown area, where friendly locals welcome you, and enjoy a romantic getaway within walking distance of top attractions. Nearby regions provide family-friendly excursions and a relaxing atmosphere, ensuring an unforgettable experience in this beautiful English city.

  • Southampton: Located approximately 19.3km from Winchester, Southampton is a vibrant city known for its rich maritime history and dynamic urban atmosphere. The city offers an array of outdoor adventures, including beautiful beachfront activities and explorations in nearby national parks. Visitors can indulge in shopping at the bustling mall centres, enjoy performances at local theatres, and experience diverse educational venues. Key attractions include the picturesque marina, where you can enjoy waterfront views, and the surrounding national parks that offer stunning landscapes for hiking and nature walks.
  • Kings Worthy: Nestled in the Winchester area, Kings Worthy is a charming village that provides a serene escape into nature. Ideal for those seeking outdoor activities and scenic beauty, this locale features recreational areas and golf courses where visitors can enjoy leisurely rounds. The nearby national parks and marinas enhance the village's appeal, offering opportunities for hiking and water-based activities. Kings Worthy is perfect for a relaxed day trip, allowing you to soak in the tranquil English countryside while enjoying its lush greenery and peaceful surroundings.
  • Sutton Scotney: Also situated near Winchester, Sutton Scotney is a quaint village that caters to families and culture enthusiasts. This vibrant community offers a variety of entertainment options, including shopping centres and an arena that hosts various events. Families can have fun exploring local theme parks and sports facilities, making it an ideal destination for a family day out. The village's welcoming atmosphere, combined with its engaging attractions, makes Sutton Scotney a delightful choice for those looking to immerse themselves in local culture while enjoying ample entertainment.

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 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 simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the perfect option for your needs!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, refine your existing arrangements, or keep track of your bookings. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/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 Paultons Family Theme Park - Home of Peppa Pig World 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:

  • Paultons Family Theme Park - Home of Peppa Pig World (13 mi / 21 km)
  • Marwell Zoo (4.8 mi / 7.7 km)
  • Broadlands Estate (9.5 mi / 15.3 km)
  • The Common (10 mi / 16.1 km)
  • Leisure World (11.8 mi / 18.9 km)
  • New Forest Wildlife Park (14.5 mi / 23.4 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)
  • Gilbert White's House and Garden and The Oates (16.1 mi / 26 km)
  • Calshot Beach (16.9 mi / 27.1 km)
  • Exbury Gardens and Steam Railway (18.3 mi / 29.4 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?
One of the more in-demand neighborhoods to book a vacation rental in Winchester is Sutton Scotney. Discover your dream stay with Vrbo and experience this area just like a local.
What is the most popular type of vacation rental accommodation in Winchester?
The most desirable types of vacation rentals in Winchester are apartments. After something a little different? Vrbo has a variety of options to match the diverse needs of our guests, so you’ll see vacation properties in lots of sizes and shapes. The ideal fit is waiting for you — get yours today.
How much does it cost to rent a vacation rental in Winchester?
A range of factors influence how much you’ll pay for a vacation rental in Winchester, such as the season, type of property and length of stay. Still, all Vrbo homes have one thing in common — unbeatable value. Simply add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Winchester?
Prices for beach houses in Winchester vary depending on the style and size of the property and time of year you’re traveling. All you need to do is enter your travel dates into Vrbo and the number of guests to see available options and prices. From there you can use our filters to narrow your search results by ratings, amenities, nearby activities and more.
Are there pet-friendly vacation rentals in Winchester?
With 47 vacation rentals that allow pets, your furry friend can join you on your Winchester getaway. Use our filter tool to browse our pet-friendly vacation rentals and find a stay that’s pawfect on Vrbo.
What are popular rental amenities in Winchester?
The most popular rental amenities people look for in Winchester include tennis, a nearby river and a fireplace. Whether you’re vacationing with family, your besties or even pets, Vrbo vacation properties provide the best amenities for hanging out with the people you cherish the most.
Are there large group vacation rentals in Winchester?
With 11 Winchester vacation rentals that can host five or more people, you can bring a few extra pals or family members along. Whether you’re planning a casual gathering or a birthday party, we’ll help you find a comfortable space to match the occasion.
Are there vacation rentals in Winchester that welcome kids?
Gather your whole family for the adventure of a lifetime in Winchester at one of our 47 family-friendly vacation homes. A lot of these stays come with conveniences that are suitable for getaways with children, including full kitchens, multiple bedrooms and outdoor spaces. Simply check the “Properties good for families” filter box and select your favorite.
What are the top attractions for families in Winchester?
Keep the kids occupied at these top family-friendly attractions in Winchester:

  • Marwell Zoo
  • Winchester Science Centre and Planetarium
  • Great Hall

Are there one-bedroom vacation rentals in Winchester?
Yes, you’ll find 16 one-bedroom properties in Winchester to pick from. A one-bedroom vacation property is a great option if it’s just you and your sweetheart or if you’re traveling alone. Add in more privacy, convenience and space compared to a standard hotel, and you’ve got the makings of an unforgettable getaway.
Can I find two-bedroom vacation rentals in Winchester?
Gather your nearest and dearest and enjoy a relaxing escape in one of the 20 two-bedroom vacation homes Winchester has to offer.
Are there vacation rentals with WiFi in Winchester?
Winchester has 13 vacation rentals with WiFi, so you can stay connected while on vacation. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming movie blockbusters to checking emails, these Vrbo homes will keep you online.
How old do you have to be to rent a vacation rental in Winchester?
The age limit can differ across properties on Vrbo, so double-check the rules of the vacation home in Winchester you want. But usually, it’s 16, 18 or 21.
How long can I rent a vacation rental in Winchester for?
It’s up to the Winchester property. To browse available options offering extended stays, simply enter your travel dates and number of people into Vrbo’s search page. You can enjoy having the place to yourself, along with home comforts such as air conditioning, a kitchen and a yard where the kids can run and play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.