Winchester holiday lettings

We found 665 holiday rentals — enter your dates for availability

Discover a selection of 36 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.

Holiday rentals with weekly discounts - Winchester

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Find out more about Winchester

Find out more about Winchester

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)
  • 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 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)
  • 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)

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 a holiday rental in Winchester, a popular area to stay is the city centre. This vibrant neighbourhood is steeped in history and offers a charming atmosphere, making it ideal for visitors looking to explore the city's rich heritage. Staying in the city centre places you within walking distance of top attractions such as the magnificent Winchester Cathedral, an architectural marvel that dates back to the 11th century, and the historic Great Hall, home to the legendary Round Table of King Arthur.

Additionally, the city centre is laden with delightful shops, cafes, and restaurants, providing a great blend of convenience and local culture. The area boasts a varied selection of holiday rentals, with a range of properties available to suit different preferences and budgets, ensuring you can find the great base for your stay.

Another excellent option is the area around the picturesque Water Meadows. This tranquil setting offers beautiful views and a peaceful retreat, while still being close to the heart of the city. You can enjoy scenic walks along the River Itchen and easily access attractions such as the Winchester Science Centre and Planetarium. Properties in this area tend to be slightly more spacious and often feature lovely gardens, making it a fantastic choice for families or those seeking a serene environment.
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 rental, with around 24 available throughout the city. These houses typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. The charming cottages, numbering about 22, provide a quaint and cosy atmosphere, often featuring traditional décor and lovely gardens, great for enjoying the historic surroundings. Additionally, there are around 20 apartments, which tend to be located in the city centre, close to points of interest like the Winchester Cathedral and the Great Hall. These apartments usually come with modern amenities, including Wi-Fi and laundry facilities. Although there are also several chalets and villas, they are less common compared to houses, cottages, and apartments.
Are there any family house rentals in Winchester?
In Winchester, there are numerous family-friendly house rentals available, with around 33 options to choose from. This historic city offers a delightful mix of culture and outdoor activities, making it an excellent choice for groups travelling with children. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and private gardens where kids can play safely.
Can I rent a holiday home with a pool or hot tub in Winchester?
In Winchester, there are several holiday homes available for rent that feature pools or hot tubs, making it an appealing destination for those seeking relaxation. This historic city, known for its stunning architecture and rich heritage, offers a range of properties located in charming neighbourhoods. Many of these rentals provide amenities such as private pools, hot tubs, and outdoor seating areas, ideal for unwinding after a day of exploring. Fully equipped kitchens are common, allowing guests to enjoy home-cooked meals while enjoying the comfort of their accommodation.
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 several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these rentals can be found in and around the city centre, offering easy access to local attractions such as the historic Winchester Cathedral and the picturesque Great Hall, home to the legendary King Arthur's Round Table.

Expect amenities such as well-equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy some fresh air. Some properties may also feature private gardens or patios, great for relaxing after a day of exploring. See all pet-friendly rentals in Winchester.
Are there any remote work holiday rentals in Winchester?
In Winchester, there are numerous holiday rentals suitable for remote work, with around 57 options available throughout the city. Travellers can expect properties equipped with essential amenities such as high-speed Wi-Fi, dedicated workspace areas, and comfortable furniture designed for productivity, including desks and ergonomic chairs. Many rentals also offer additional conveniences like safes for secure storage and laptop-friendly spaces, ensuring a comfortable work environment. 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, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals, as well as complimentary Wi-Fi for staying connected. Many rentals also feature essential cookware, dishware, and utensils, making it easy to dine in. Additionally, properties often come with modern appliances such as ovens and dishwashers, enhancing convenience for travellers.
When is the best time to visit Winchester for a holiday rental?
September is the most popular month to visit Winchester, drawing in travellers eager to soak up the rich history and vibrant culture of this charming city. The peak season runs from July to September, when the weather is pleasantly warm, making it superb for exploring the stunning architecture and beautiful parks. Visitors can indulge in leisurely strolls through the historic streets, admire the magnificent Winchester Cathedral, or enjoy the lively atmosphere of local markets.

During this time, average temperatures hover around the low 20s Celsius, providing ideal conditions for outdoor activities and sightseeing. The city is adorned with lush greenery, and there are plenty of events and festivals that enhance the overall experience, ensuring you feel the pulse of Winchester's vibrant community.

For travellers seeking a more budget-friendly option, May offers a great alternative. While the temperatures are slightly cooler, typically in the mid-teens Celsius, the tranquillity of the city during this month allows for uninterrupted exploration of Winchester's historical sites without the hustle and bustle of peak tourist crowds.
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.
What are the top attractions in Winchester?
In Winchester, visitors can experience firsthand a rich tapestry of history and culture. The iconic Winchester Cathedral, a stunning example of Gothic architecture, is a must-see and often features holiday rentals within walking distance, allowing guests to explore its impressive interiors and beautiful grounds at their leisure. The historic Great Hall, home to the legendary Round Table of King Arthur, is another key attraction located near the city centre, making it convenient for those staying nearby.

Stroll through the picturesque streets of the city, particularly in the charming area around the High Street, where you can discover an array of independent shops, cafes, and traditional pubs. The tranquil River Itchen runs through the city, offering scenic walks and spots for picnicking, with several rental properties situated close to the riverside.
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 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 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.