Winchester holiday lettings

We found 273 holiday rentals — enter your dates for availability

Discover a selection of 40 homes, 40 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 sites: Visit the stunning Winchester Cathedral and explore the city's rich history through its museums and colleges.
  • Scenic beauty: Enjoy the picturesque landscapes of Hampshire, perfect for outdoor adventures and leisurely strolls.
  • Welcoming locals: Experience the warmth of friendly locals who enhance the charm of this delightful city.
  • Diverse accommodation: Choose from charming cottages, spacious holiday homes, and stylish apartments for a comfortable stay.
  • Family-friendly activities: Engage in a variety of activities suitable for all ages, ensuring a memorable visit for everyone.

Popular types of accommodation in Winchester

If you’re wondering about accommodation options in Winchester, look no further. Our most popular choices include charming cottages in Winchester, spacious private holiday homes, and stylish apartments. Whether you’re seeking a quaint lodge or a holiday cottage near Winchester College, we have a variety of options to suit your needs. Enjoy the historic charm of this beautiful city while staying in comfort and style.

  • Apartments: A highly sought-after option, apartments in Winchester offer modern amenities and convenience for both short and extended stays.
  • Houses: Ideal for families or groups, these homes provide a comfortable and private setting for your holiday.
  • Cottages: Charming and picturesque, cottages in the countryside offer a quaint retreat with a touch of traditional English charm.
  • Caravan Parks: For a unique experience, caravan parks provide a sociable atmosphere with various facilities to enjoy the outdoors.
  • Cabins: A rustic choice, cabins are perfect for those seeking a tranquil escape amidst nature.**

Top attractions in and around Winchester

Winchester offers a delightful blend of outdoor adventures and rich history, making it an ideal destination for your holiday. You can explore the stunning Winchester Cathedral, along with various historic colleges, museums, and houses. This charming city caters to those seeking cultural experiences and family-friendly activities, ensuring a memorable visit for everyone. Don't miss the opportunity to enjoy the scenic beauty and heritage that Winchester has to offer.

  • Winchester Cathedral: A stunning example of Gothic architecture, Winchester Cathedral boasts a rich history dating back to the 7th century. Visitors can admire its intricate stained glass, beautiful wooden ceilings, and tranquil grounds, all while soaking in the cultural atmosphere of this iconic landmark.
  • Paultons Family Theme Park - Home of Peppa Pig World: Located 8.1km from Winchester, this family-friendly theme park features rides and attractions themed around Peppa Pig. It's a delightful place for families to enjoy entertainment and create lasting memories in a vibrant, whimsical setting.
  • University of Winchester: This historic university offers picturesque campus grounds and a vibrant academic atmosphere. Visitors can explore its beautiful architecture, gardens, and cultural events, making it a lovely spot to appreciate the educational heritage of the area.

Things to do recommended for couples

Winchester offers delightful romantic experiences for couples. Visit Raimes English Sparkling, a charming winery just 3.1km away, or enjoy the enchanting Wickham Estate, 6.8km out, for a perfect blend of romance and entertainment. For an adventurous twist, try Alpine Snowsports Southampton, also 6.8km distant.

Things to do recommended for families

Families will have a fantastic time at the Winchester Science Centre and Planetarium, offering educational fun. For sports enthusiasts, the Ageas Bowl Cricket Ground is just 5.6km away, while adventure seekers can enjoy indoor go-karting at TeamSport, located 3.7km from Winchester.

Things to do recommended for groups

In Winchester, groups can enjoy shopping at the WestQuay Shopping Centre, catch a show at Theatre Royal Winchester for a taste of local culture, and visit the Bombay Sapphire Distillery for a delightful experience in distilling and romance.

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

When planning your trip, whether it's with a group, family, pets, or for an extended stay, be sure to apply the appropriate filters to meet your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Winchester with a group: Think about how many bedrooms you’ll require, as well as any amenities like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these features and much more on Vrbo.
  • Traveling to Winchester with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, along with suitable amenities, like private swimming pools. Additionally, it’s wise to take into account your closeness to attractions that are family-friendly.
  • Taking your pets with you to Winchester: For many families, a holiday isn't truly enjoyable without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Many pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of the family 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 more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider including features such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in and around Winchester

Discover the charming city of Winchester, a beautiful English gem steeped in history and surrounded by stunning scenery. Explore the central area, where friendly locals welcome you with warmth. Venture into Hampshire, known for its idyllic locations and family-friendly atmosphere. Whether seeking outdoor adventures or relaxing excursions, Winchester offers a delightful mix of experiences for every traveller.

  • Southampton: Situated 7.5km from Winchester, Southampton is a vibrant city known for its rich maritime history and lively atmosphere. This coastal destination offers visitors an array of outdoor adventures, including beautiful beaches and scenic parks. Explore the bustling shopping centres, enjoy a performance at the local theatre, or take a stroll along the marina. With attractions such as the New Forest National Park nearby, Southampton is perfect for those seeking both urban experiences and natural beauty.
  • Eastleigh: Located 4.3km from Winchester, Eastleigh is a charming city that caters to families and adventure-seekers alike. Visitors can enjoy a variety of recreational activities, including trips to local theatres and educational venues. The city is also home to picturesque parks and a popular theme park that provides entertainment for all ages. With its welcoming atmosphere and proximity to natural landscapes, Eastleigh is an excellent spot for a fun-filled day out.
  • Sutton Scotney: Nestled within the Winchester area, Sutton Scotney is a delightful village that offers a blend of family-friendly activities and cultural experiences. With a shopping centre and arena entertainment facility, there's something for everyone in this quaint locale. Explore nearby attractions such as a theme park and local sports stadium, providing plenty of entertainment options. Sutton Scotney's tranquil setting and community spirit make it a lovely stop during your exploration of the region.

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 holiday? It might be worth considering some flexibility with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's user-friendly Trip Board offers you a dedicated space to plan new getaways, pick up from where you last stopped, or review and manage your travel arrangements. You can easily access the properties you've saved and booked, now organised under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-gb/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)
  • The Common (10 mi / 16.1 km)
  • Leisure World (11.8 mi / 18.9 km)
  • Paultons Family Theme Park - Home of Peppa Pig World (13 mi / 21 km)
  • Thruxton Kart Centre (16.3 mi / 26.3 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)
  • 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)
  • Meon Shore Beach (16.9 mi / 27.2 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.
How much does it cost to rent a holiday home in Winchester?
Prices for holiday 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 holiday 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.
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.
Can I find long-stay holiday rentals in Winchester?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 Vrbo.
Are there any Winchester holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 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, 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.
How early should I book a Winchester holiday rental?
Book your Winchester holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Winchester home rental booking on Vrbo?
To find Winchester holiday 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 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 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, Vrbo 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 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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