Winchester holiday homes

We found 291 holiday rentals — enter your dates for availability
Discover a selection of 37 homes, 44 apartments and other holiday rentals in Winchester that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for spending time at your holiday home, such as Wi-Fi and cable TV. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Why visit Winchester

  • Historic architecture: Discover Winchester Cathedral, the Great Hall, and medieval streets that echo the city's storied past.
  • Cultural heritage: Immerse yourself in museums and historic houses that showcase Winchester's rich traditions.
  • Scenic beauty: Enjoy urban parks and picturesque views, perfect for leisurely strolls and outdoor adventures.
  • Educational charm: Explore Winchester College and other landmarks that reflect the city's academic history.
  • Local ambience: Wander through vibrant streets lined with local shops and experience the friendly local vibe.

Top attractions in and around Winchester

Winchester, England, United Kingdom offers a blend of culture and outdoor adventure perfect for tourists from New Zealand. Explore its rich history through museums, historic houses, and urban parks. Enjoy family-friendly attractions with a focus on culture, outdoor experiences, and scenic beauty. Discover the charm of Winchester as you immerse yourself in its renowned landmarks and local experiences during your holiday.

  • Winchester Cathedral: This magnificent cathedral boasts stunning Gothic architecture and a rich history, offering a serene atmosphere and cultural vibes. Visitors can explore its beautiful stained glass windows, intricate stonework, and the tomb of Jane Austen.
  • Paultons Family Theme Park - Home of Peppa Pig World: Experience a fun-filled day with the family at this vibrant theme park, featuring rides and attractions based on the beloved Peppa Pig series. It's perfect for families looking for entertainment and memorable experiences.
  • Avington Park: A stunning historic house surrounded by picturesque gardens, Avington Park offers a glimpse into England's heritage. The property features beautiful grounds and cultural vibes, ideal for a leisurely stroll or a picnic.

Things to do recommended for couples

Experience a romantic getaway in Winchester. Stroll hand in hand through charming streets and savour intimate moments at cosy local cafés. Enjoy a serene walk alongside the River Itchen and discover hidden gems that make your visit uniquely memorable.

Things to do recommended for families

Families will love exploring the interactive exhibits at the Winchester Science Centre, wandering through the beautiful gardens of the Great Hall, and encountering the fascinating wildlife at Marwell Zoo. Don't miss a stroll through the historic streets, soaking up the local charm and culture.

Things to do recommended for groups

Gather your mates for an adrenaline rush at Thruxton Kart Centre, a motorRacing hotspot located 26km from Winchester, offering sports and adventure vibes perfect for your group holiday.

*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 travelling with a group, family, or pets, or if you're considering a longer stay, it's important to filter your options according to 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 fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all 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 prioritise their comfort and safety, along with ensuring access to 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 trip isn’t truly complete without their furry companion. If you can relate, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winchester: If you're in search of holiday rentals offering discounts for stays of a month or longer, 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.

Where to stay in and around Winchester

Winchester, England, is a delightful city steeped in history and charm. Explore the stunning medieval architecture, including the iconic Winchester Cathedral and the ancient Great Hall, home to the legendary Round Table. Stroll through the quaint streets of central Winchester, where you'll find a mix of friendly locals and vibrant shops. Don't miss the prestigious Winchester College, offering a glimpse into the city's rich educational heritage. With its scenic views and welcoming atmosphere, Winchester promises an unforgettable travel experience.

  • Southampton: Southampton, a vibrant city 19km from Winchester, is a hub for those seeking outdoor adventures and scenic beauty. The city offers a mix of urban excitement and natural charm, with attractions ranging from expansive shopping centres and dynamic theatres to bustling shopping areas. Explore the local marina, and enjoy the stunning views of the nearby national park and state park. This destination provides a rich travel experience, combining modern city life with the great outdoors.
  • Twyford: Twyford is a quaint village within the Winchester area, perfect for travellers keen on outdoor exploration and adventure. The village is surrounded by remarkable natural landscapes, including a national park and state park, and is known for its significant architectural landmarks. A recreational area provides ample opportunity for a relaxed day out in the fresh air, making it an ideal spot for those looking to immerse themselves in local heritage and nature.
  • Hursley: Hursley, another charming village in the vicinity of Winchester, offers a blend of adventure and scenic delight. The area is celebrated for its access to expansive national and state parks, alongside a historic building that speaks to the rich local history. Whether exploring the rugged outdoors or delving into the village's storied past, Hursley presents a compelling destination for those seeking both cultural insights and natural beauty.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January40.3°F (4.6°C)Light RainMostly CloudyAverage
February41.2°F (5.1°C)Light RainMostly CloudyAverage
March43.9°F (6.6°C)Light RainMostly CloudyAverage
April47.8°F (8.8°C)Light RainMostly CloudyAverage
May53.2°F (11.8°C)Light RainMostly CloudySlightly Low
June59.2°F (15.1°C)Light RainMostly CloudyAverage
July62.8°F (17.1°C)Light RainMostly CloudySlightly High
August62.1°F (16.7°C)Light RainMostly CloudyAverage
September58.6°F (14.8°C)Light RainMostly SunnySlightly High
October53.4°F (11.9°C)Light RainMostly CloudySlightly Low
November46.8°F (8.2°C)Light RainMostly CloudySlightly High
December43.0°F (6.1°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is simple

If you’re keen to trim costs on your upcoming adventure, why not consider a bit of flexibility with your travel dates? Prices can vary, so being open to different options might save you a pretty penny. Additionally, opting for a longer stay often brings considerable savings. To help you find the perfect Vrbo accommodation that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's clever Trip Board offers you a dedicated space to plan new adventures, pick up from where you last stopped, or manage your travel arrangements. You can easily access properties you’ve saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Historical Winchester will entice you

Take a holiday 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-see attractions 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

Are you searching for attractions to visit in the city? Venture out of your cosy holiday rental and experience everything that Winchester has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Marwell Zoo (4.8 mi / 7.7 km)
  • Broadlands Estate (9.5 mi / 15.3 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)
  • SenSpa at Careys Manor Hotel (20.1 mi / 32.3 km)

Exploring the gardens and other natural features in Winchester

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Winchester is a great spot to appreciate mother nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • New Forest National Park (19.6 mi / 31.5 km)
  • Mayflower Park (12 mi / 19.3 km)
  • Calshot Beach (16.9 mi / 27.1 km)
  • Exbury Gardens and Steam Railway (18.3 mi / 29.4 km)
  • Lepe Beach (19.1 mi / 30.8 km)
  • Stansted Park (20.6 mi / 33.1 km)

Transport to and around Winchester

The nearest airport is in Southampton (SOU), located 7.9 mi (12.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying 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 that serve the city.

Frequently asked questions

What is the best area to stay in Winchester when booking a holiday rental?
When considering the best area to stay in Winchester, England, a delightful choice would be the city centre. This charming area is brimming with historical significance and provides easy access to some of the city's top attractions, including the breathtaking Winchester Cathedral and the Great Hall, which houses the legendary Round Table of King Arthur. Staying in the city centre allows you to immerse yourself in the local culture, with a variety of shops, cafes, and restaurants right at your doorstep.Another appealing neighbourhood is the picturesque area surrounding the River Itchen. Known for its scenic walks and beautiful riverside views, this area offers a tranquil retreat while remaining close to the vibrant setting of the city. Here, you can enjoy a leisurely stroll along the riverbanks or explore the lovely gardens nearby.In terms of accommodation options, Winchester boasts a diverse range of holiday rentals, with numerous properties available in both the city centre and the riverside area. This variety ensures that visitors can find the superb place to suit their preferences, whether they are seeking a modern flat or a quaint cottage.
What is the most popular type of holiday rental accomodation in Winchester?
In Winchester, holiday houses are the most popular type of holiday rental, with about 78 available throughout the city. These properties often feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking to enjoy a home-like experience. Many also come with outdoor spaces such as gardens or patios where guests can relax and soak up the charming atmosphere of this historic city.Apartments are also quite sought after, with around 72 options available, typically situated in convenient locations near points of interest like the Winchester Cathedral and the Great Hall. These apartments usually offer modern amenities, including cosy living areas and kitchens.Additionally, there are approximately 63 cottages within the area, which provide a quaint and traditional feel, great for those wanting a unique stay. While there are several cabins and chalets available, they are less common compared to the other types of rentals.
Are there any family house rentals in Winchester?
In Winchester, there are plenty of family-friendly house rentals available, with around 28 options throughout the area. This historic city, known for its stunning cathedral and charming streets, offers various accommodations suitable for families. Many of these properties feature spacious living areas, well-equipped kitchens for preparing family meals, and outdoor spaces where children can play safely.Visitors will appreciate the proximity to local attractions such as the Great Hall and the picturesque River Itchen, superb for leisurely walks or picnics. Additionally, the bustling city centre with its shops, cafes, and restaurants is easily accessible.
Are there pet-friendly house rentals in Winchester?
In Winchester, there are numerous pet-friendly house rentals available, with around 30 options to choose from. Many of these properties are located in and around the picturesque city centre, offering a range of amenities such as fully equipped kitchens, spacious living areas, and private gardens or courtyards, superb for travellers with pets.The charming streets of Winchester are ideal for leisurely strolls, and the nearby River Itchen provides lovely walking paths for pet owners. Additionally, the beautiful South Downs National Park is easily accessible, offering expansive green spaces and scenic trails where dogs can enjoy plenty of exercise. See all pet-friendly rentals in Winchester.
Are there any remote work holiday rentals in Winchester?
In Winchester, there are numerous remote work holiday rentals available, with around 186 options to choose from. The city offers a delightful blend of historical charm and modern amenities, making it an excellent choice for those looking to work remotely. Many properties come equipped with essential amenities such as free Wi-Fi, dedicated workspaces including desks and chairs, and comfortable living spaces to ensure a productive environment.Staying in areas close to the city centre allows easy access to local cafes and eateries, great for a change of scenery while working. Additionally, Winchester is home to points of interest like the stunning Winchester Cathedral and the historic Great Hall, providing ample opportunities for exploration during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Winchester?
In Winchester, holiday rentals often feature a range of popular amenities that cater to different traveller needs. Most properties include a fully equipped kitchen, allowing guests to prepare their meals conveniently. Onsite parking is commonly available, making it easy for those travelling by car. Many rentals also boast outdoor spaces, such as decks or patios, where visitors can relax and enjoy the fresh air, particularly after exploring the historic sites of the city, like the Winchester Cathedral and the Great Hall. Additionally, some rentals are pet-friendly, permitting guests to bring their furry companions along, with provisions for service animals as well.
When is the best time to visit Winchester for a holiday rental?
September is the most popular time to visit Winchester, as the summer crowds begin to thin, yet the weather remains pleasantly mild. The peak season, which runs from July to September, sees the city bustling with tourists eager to explore its rich history and beautiful architecture, including the magnificent Winchester Cathedral and the Great Hall.During these summer months, temperatures typically hover around 15 to 25 degrees Celsius, providing ideal conditions for outdoor activities such as strolling through the historic streets and enjoying picnics in the picturesque gardens. In September, you can experience the charm of Winchester with fewer tourists, allowing for a more relaxed exploration of its attractions.For those seeking a more budget-friendly option, May is an excellent time to visit. This month offers lovely spring weather, with temperatures ranging from 10 to 20 degrees Celsius, and the added bonus of blooming flowers in the city's parks and gardens. May is superb for leisurely walks and sightseeing without the hustle and bustle of peak season.Ultimately, choosing the best time for a holiday rental in Winchester will depend on your preferences for lively events and socializings during the summer or a quieter, more peaceful experience in the spring.
Are all fees included in the Winchester holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Winchester holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Winchester with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Winchester holiday homes?
You can find great discounts on holiday homes in Winchester on Bookabach, 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.
Can I change or cancel my Winchester holiday home booking on Bookabach?
To find Winchester holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Winchester?
A long-stay holiday home in Winchester is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Winchester holiday home?
Book your Winchester holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winchester?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Winchester to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers 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, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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