Winchester holiday rentals

We found 274 holiday rentals — enter your dates for availability
Discover a selection of 41 homes, 41 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 Cathedral: Discover the magnificent Winchester Cathedral, a timeless emblem of the city’s rich heritage.
  • Ancient Guildhall: Explore the storied Winchester Guildhall, a testament to medieval English history.
  • Cultural Museums: Immerse yourself in the city’s past through its captivating museums.
  • Urban Parks: Wander through scenic urban parks that offer a blend of nature and history.
  • Charming Streets: Experience the vibrant atmosphere of Winchester’s historic streets, perfect for family adventures.

Popular types of accommodation in Winchester

Discover Winchester, a city steeped in history, offering charming attractions, landmarks, and experiences for every traveller. Enjoy a delightful stay with our selection of holiday rentals, ranging from apartments to private holiday homes and cosy cottages. Ideal for a night stay or extended visit, our friendly accommodation includes guesthouses and suitable rooms tailored for comfort and convenience. Immerse yourself in Winchester’s allure, where history meets modern living in every corner.

  • Apartments: Discover modern, self-contained flats in Winchester, perfect for a comfortable and convenient stay.
  • Private Holiday Homes: Enjoy the privacy and homely atmosphere of secluded, independent residences during your visit.
  • Cottages: Relish the charm of rustic cottages, offering a cosy retreat in the heart of the area.
  • Caravan Parks: Experience the flexibility of holiday parks with caravans, ideal for a dynamic escape.
  • Cabins: Embrace a unique stay in quaint cabins, providing a rustic yet refreshing getaway.**

Top attractions in and around Winchester

Winchester, England, offers a delightful mix of culture and outdoor charm. Explore the historic Winchester Cathedral and the ancient Winchester Guildhall, and wander through urban parks that capture the city’s rich heritage. With captivating museums and scenic spots, visitors can immerse themselves in the city's storied past and vibrant culture, making it an ideal destination for family adventures and outdoor escapades.

  • Winchester Cathedral: A stunning example of Gothic architecture, this cathedral boasts a rich history and breathtaking stained glass windows. Visitors can explore its tranquil gardens and attend services that echo centuries of tradition.
  • Paultons Family Theme Park - Home of Peppa Pig World: While not located within the city, this vibrant theme park offers a delightful family day out with rides and attractions themed around Peppa Pig, providing joy and excitement for younger visitors.
  • Jane Austen's House: A charming museum dedicated to the renowned author, showcasing her life and works. Visitors can wander through the rooms where she penned her famous novels, surrounded by period furnishings and personal artefacts.

Things to do recommended for couples

Winchester offers charming experiences for couples, such as a leisurely stroll through the picturesque streets and a visit to the stunning Winchester Cathedral. Consider a romantic picnic in the serene gardens of the city or a delightful meal at a quaint bistro, perfect for creating lasting memories together.

Things to do recommended for families

Families will love exploring the Winchester Science Centre, with its interactive exhibits and planetarium. Don't miss the enchanting Winchester Cathedral, where kids can discover history through engaging tours. Enjoy a leisurely stroll in the beautiful Winchester Great Hall, home to the legendary Round Table.

Things to do recommended for groups

Groups visiting Winchester can enjoy a local adventure at Thruxton Kart Centre, a motor racing venue located 26km from the city, offering sports and adventure vibes for an exhilarating day out.

*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

Whether you're journeying with a group, travelling with family, accompanied by your pets, or seeking extended stays, be sure to refine your search by selecting the appropriate priorities. Here are some Stayz booking tips for you.

  • Traveling to Winchester with a group: Consider the number of bedrooms required, along with facilities like a fully-equipped kitchen or an outdoor area for group get-togethers. Fortunately, you can refine your search for all these features, and more, on Stayz.
  • Traveling to Winchester with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities for their age, 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, a family holiday isn’t complete without the presence of their furry companion. If this resonates with you, explore Stayz properties that welcome pets. Most pet-friendly accommodations provide feeding bowls and beds, ensuring that everyone feels right 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 place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Winchester

Winchester, a beautiful city steeped in history, offers an array of attractions for every traveller. At the heart of historic Winchester, you'll find the magnificent cathedral, surrounded by charming streets and friendly locals. Explore the picturesque scenery and immerse yourself in the vibrant atmosphere, perfect for a relaxing family-friendly holiday. With its prime location, Winchester serves as an ideal base for discovering the fascinating heritage and culture that the city has to offer.

  • Southampton: Southampton is a vibrant city situated 19km away from Winchester, offering an engaging blend of urban excitement and natural splendour. Visitors are drawn to its outdoor, adventurous character and scenic views. The city is a hub for a range of activities, from exploring its bustling shopping mall centre and theatre to wandering through its extensive shopping areas. Nearby, travellers can admire notable landmarks such as the marina, national park, and national state park, making Southampton a compelling destination for both cultural aficionados and nature enthusiasts.
  • Sparsholt: Sparsholt, a quaint village nestled within the Winchester area, exudes a serene countryside charm. Renowned for its outdoor and adventurous spirit, the village is ideal for those seeking to immerse themselves in the beauty of the English landscape. Activities in the area include educational pursuits, golf, and motor racing. Also, the region boasts attractions like a national park, a historic college university, and a national state park, offering a delightful mix of natural scenery and historical interest.
  • Twyford: Twyford is a picturesque village located in the Winchester vicinity, perfect for travellers who appreciate the great outdoors and a sense of adventure. With a focus on the recreational area, visitors can enjoy the region's natural beauty and partake in various outdoor pursuits. The proximity to attractions such as a national park, a national state park, and significant examples of architecture further enhances its appeal, making Twyford a delightful retreat for those eager to explore both the natural and cultural heritage of the area.

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 Stayz is simple

Looking to cut costs on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, opting for a longer stay can often result in substantial savings. To discover the ideal Stayz property that fits your budget, utilise our filters to refine your search by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s Trip Board offers you a handy space to initiate new journeys, continue where you last stopped, or review and organise your plans. Here, properties you’ve favourited or reserved are neatly arranged under Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/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)
  • Clarence Pier (21 mi / 33.8 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)
  • Calshot Beach (16.9 mi / 27.1 km)
  • Meon Shore Beach (16.9 mi / 27.2 km)
  • Lee-on-the-Solent Beach (18 mi / 28.9 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 Stayz.
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 Stayz?
Stayz 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?
Stayz 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 Stayz, 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 Stayz?
To find Winchester holiday rentals with free cancellation, just use Stayz'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, Stayz 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 Stayz?
Stayz'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 Stayz 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. Stayz offers something for every taste and budget, from affordable homes in Winchester to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz 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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