Winchester holiday rentals

We found 289 holiday rentals — enter your dates for availability

Discover a selection of 45 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.
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

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)
  • Thruxton Circuit (16.4 mi / 26.4 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)
  • Hawk Conservancy Trust (14.9 mi / 24 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 home?
One of the more in-demand neighbourhoods to book a holiday home in Winchester is Sutton Scotney. Discover your dream stay with Stayz and experience this area just like a local.
What is the most popular type of holiday home accommodation in Winchester?
The most desirable types of holiday homes in Winchester are apartments. After something a little different? Stayz has a variety of options to match the diverse needs of our guests, so you'll see holiday properties in lots of sizes and shapes. The ideal fit is waiting for you — get yours today.
How much does it cost to rent a holiday home in Winchester?
A range of factors influence how much you'll pay for a holiday home in Winchester, such as the season, type of property and length of stay. Still, all Stayz homes have one thing in common — unbeatable value. Simply add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Winchester?
Prices for beach houses in Winchester vary depending on the style and size of the property and time of year you're travelling. All you need to do is enter your travel dates into Stayz and the number of guests to see available options and prices. From there you can use our filters to narrow your search results by ratings, amenities, nearby activities and more.
Are there pet-friendly holiday homes in Winchester?
With 47 holiday homes that allow pets, your furry friend can join you on your Winchester getaway. Use our filter tool to browse our pet-friendly holiday homes and find a stay that's pawfect on Stayz.
What are popular home amenities in Winchester?
The most popular home amenities people look for in Winchester include tennis, a nearby river and a fireplace. Whether you're holidaying with family, your besties or even pets, Stayz holiday properties provide the best amenities for hanging out with the people you cherish the most.
Are there large group holiday homes in Winchester?
With 11 Winchester holiday homes that can host five or more people, you can bring a few extra pals or family members along. Whether you're planning a casual gathering or a birthday party, we'll help you find a comfortable space to match the occasion.
Are there holiday homes in Winchester that welcome kids?
Gather your whole family for the adventure of a lifetime in Winchester at one of our 47 family-friendly holiday homes. A lot of these stays come with conveniences that are suitable for getaways with children, including full kitchens, multiple bedrooms and outdoor spaces. Simply check the "Properties good for families" filter box and select your favourite.
What are the top attractions for families in Winchester?
Keep the kids occupied at these top family-friendly attractions in Winchester:

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

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