Winchester vacation rentals

We found 627 vacation rentals — enter your dates for availability

Discover a selection of 39 homes, 39 apartments, and other vacation rentals in Winchester that are perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the amenities you expect for your stay, which might include cable TV and a washer and dryer. No matter what you're looking for, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Winchester

Showing deals for:Feb 27 - Mar 6

Image gallery for Lovely cottage & garden. 5 min drive from Paultons Park, home of Peppa Pig

Front of cottage
9.4 out of 10, Exceptional, (118 reviews)
Exceptional
(118 reviews)

Lovely cottage & garden. 5 min drive from Paultons Park, home of Peppa Pig

Southampton, ENG

20% off
Price is CA $275
CA $2,375 total
includes taxes & fees
Lovely cottage & garden. 5 min drive from Paultons Park, home of Peppa Pig

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Find out more about Winchester

Why visit Winchester

  • Historic landmarks: Discover the majestic Winchester Cathedral and the iconic Winchester Castle, rich in history.
  • Scenic countryside: Enjoy the stunning landscapes of Hampshire and Berkshire, perfect for outdoor activities.
  • Vibrant downtown: Explore unique shops and delightful cafes, where friendly locals create a welcoming atmosphere.
  • Family-friendly adventures: Engage in a variety of activities suitable for all ages amidst beautiful surroundings.
  • Diverse accommodations: Choose from charming apartments, private homes, and delightful cottages for a comfortable stay.

Popular types of accommodation in Winchester

Looking for vacation rentals in Winchester? Our platform offers a variety of accommodations to suit your needs, including cozy apartments, charming houses, and delightful cottages. Whether you're searching for Airbnb options or considering hotels, Winchester has something for every Canadian traveler. Dive into a comfortable stay that provides transparency, savings, and reassurance while you explore this beautiful destination.

  • Apartments: The top choice for vacation rentals in Winchester, offering modern amenities and convenient locations for a comfortable stay.
  • Houses: A fantastic option for families or groups seeking a homely atmosphere with plenty of space and privacy.
  • Cottages: These quaint retreats provide a cozy and picturesque setting, perfect for a peaceful getaway.
  • Caravan Parks: A unique experience for those looking to enjoy the outdoors with facilities for caravans and camping.
  • Cabins: A charming option for nature enthusiasts wanting a rustic escape in the beautiful countryside.**

Top attractions in and around Winchester

Winchester, England, is an ideal destination for outdoor enthusiasts and culture seekers alike. Explore historic sites like Winchester Castle and Winchester Cathedral, immerse yourself in local museums, and enjoy family-friendly adventures amidst stunning scenery. Whether you’re visiting for history or outdoor fun, Winchester offers a range of attractions that cater to all travellers. Don’t miss the chance to experience the charm of this beautiful city during your vacation.

  • Winchester Cathedral: This magnificent cathedral boasts stunning Gothic architecture and rich history, making it a cultural gem. Explore its beautiful stained glass windows and serene gardens.
  • Paultons Family Theme Park - Home of Peppa Pig World: A delightful family-friendly theme park featuring attractions based on the beloved Peppa Pig series. Enjoy thrilling rides and whimsical experiences perfect for children.
  • University of Southampton: A prestigious institution with a vibrant campus and historic architecture. Discover its beautiful grounds and rich academic culture, ideal for those interested in higher education.

Things to do recommended for couples

For a romantic getaway in Winchester, explore Alpine Snowsports Southampton for some exhilarating skiing just 17.7km away. Indulge in the charm of Raimes English Sparkling, a delightful winery 8.0km from the city, or visit Wickham Estate, another enchanting winery offering romance and entertainment, located 17.7km away.

Things to do recommended for families

Your family will love visiting St. Mary's Stadium for an exciting sports experience, Frankie's Fun Factory for arcade adventure, and The Quays for some fun aquatic activities, all within a short drive from Winchester. Each place offers a unique and enjoyable atmosphere for everyone.

Things to do recommended for groups

Groups visiting Winchester can enjoy shopping at WestQuay Shopping Centre, experience the cultural charm of Theatre Royal Winchester, and indulge in an entertaining tour at the Bombay Sapphire Distillery. Each location offers a unique blend of vibes perfect for group travelers seeking local experiences.

*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 planning your trip—be it with friends, family, pets, or for an extended stay—it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winchester with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Winchester with young kids: Traveling with little ones can be quite the adventure. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions is wise.
  • Taking your pets with you to Winchester: For many families, a trip isn’t truly complete without their furry companion by their side. If you can relate, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winchester: If you're in search of vacation rentals offering discounts for stays of a month or more, 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 consider including amenities 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 offers a charming blend of history and scenic countryside, perfect for outdoor adventures and family-friendly excursions. Explore the vibrant downtown, where friendly locals welcome you to unique shops and delightful cafes. Just a short drive away, the stunning Hampshire countryside and secluded Berkshire provide a serene escape. Whether you’re seeking a beautiful apartment in the heart of the city or a peaceful retreat, Winchester promises an unforgettable travel experience.

  • Southampton: Located 19.3km from Winchester, Southampton is a vibrant city renowned for its outdoor adventures and coastal charm. Visitors can enjoy a variety of experiences, from exploring its bustling shopping mall centre to catching a performance at one of the many theatres. The city also offers easy access to stunning natural attractions, including the nearby marina and national parks, perfect for a day of exploration or relaxation by the water. Whether you're seeking retail therapy or a scenic stroll, Southampton has something for everyone.
  • Eastleigh: Just 11.3km from Winchester, Eastleigh is a family-friendly city that invites visitors to indulge in outdoor adventures and cultural experiences. The area boasts a range of recreational facilities, including a theatre and serene parks, making it ideal for families looking to spend quality time together. Close by, you'll find attractions like a marina and a thrilling theme park, ensuring a fun-filled day for visitors of all ages. Eastleigh offers a welcoming atmosphere with plenty to see and do.
  • Sutton Scotney: Nestled in the Winchester area, Sutton Scotney is a charming village that focuses on family entertainment and cultural experiences. This quaint locale features a variety of shopping centres and an arena entertainment facility, catering to both relaxation and leisure. Nearby, visitors can enjoy sports at local stadiums or have a blast at the nearby theme park. With its close-knit community feel and engaging activities, Sutton Scotney is perfect for those seeking a blend of entertainment and culture during their stay.

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 getaway? Being flexible with your travel dates can really make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect accommodation for your needs.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, continue from where you last stopped, or manage your travel arrangements. You’ll see your saved or booked properties neatly organized into categories such as Potential, Upcoming, or Current Trips. To begin exploring the benefits of Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Historic Winchester will entice you

Take a vacation 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. 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

Do you want to find attractions to visit during your stay? Venture out of your cozy vacation rental and experience everything that Winchester has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Thruxton Kart Centre (16.3 mi / 26.3 km)
  • Basingstoke Leisure Park (16.4 mi / 26.4 km)

Exploring the gardens and other natural features in Winchester

Whether you're an outdoor enthusiast or just want to take in the scenery, Winchester is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Avington Park (3.3 mi / 5.3 km)
  • Mayflower Park (12 mi / 19.3 km)
  • Calshot Beach (16.9 mi / 27.1 km)
  • Lee-on-the-Solent Beach (18 mi / 28.9 km)
  • Exbury Gardens and Steam Railway (18.3 mi / 29.4 km)
  • Lepe Beach (19.1 mi / 30.8 km)

Transportation to and around Winchester

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

Frequently asked questions

What is the best area to stay in Winchester when booking a vacation rental?
When considering a vacation rental in Winchester, the historic city centre is an excellent choice. This area is steeped in history and offers a wealth of attractions right on your doorstep. You'll find the magnificent Winchester Cathedral, a stunning example of Gothic architecture, and the Great Hall, which houses the legendary Round Table associated with King Arthur. The charming streets are lined with quaint shops, cafés, and restaurants, providing a delightful atmosphere for leisurely strolls.

Another fantastic option is the area around the University of Winchester. This neighbourhood offers a slightly more modern vibe while still being close to the city centre. Here, visitors can enjoy the picturesque gardens and parks that surround the university, great for a relaxing afternoon. The proximity to the city centre means you can easily access attractions like the City Museum and the beautiful River Itchen, ideal for scenic walks.
How much does it cost to rent a vacation home in Winchester?
Prices for vacation 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 travelling 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.
Are there any discounts for Winchester vacation 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 vacation rental accomodation in Winchester?
In Winchester, vacation houses are the most popular type of rental, with around 24 available throughout the city. These properties often feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or larger groups. Cottages also hold significant appeal, with about 22 options that offer a charming and traditional atmosphere, often set in picturesque locations. Additionally, there are around 20 apartments available, providing a more compact and convenient stay, typically located near the city centre, close to attractions like the Winchester Cathedral and the Great Hall. For those seeking something unique, several chalets and cabins can be found in the surrounding countryside, offering a rustic retreat with amenities that may include outdoor seating areas and scenic views.
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 is a splendid destination for families, offering a combination of cultural experiences and modern amenities. Many of the accommodations feature spacious living areas, well-equipped kitchens for preparing family meals, and private gardens where children can play safely.

Visitors will appreciate the proximity to top attractions such as the majestic Winchester Cathedral and the charming Great Hall, home to the legendary Round Table. The city also boasts beautiful parks like the North Walls Recreation Ground, which provides ample space for outdoor activities and picnics.
Can I rent a vacation home with a pool or hot tub in Winchester?
In Winchester, there are several vacation homes available for rent that feature pools or hot tubs, making it an appealing destination for travellers seeking relaxation. The charming city, steeped in history, offers rentals in various neighbourhoods, including the picturesque area surrounding the Cathedral and the more tranquil outskirts, where properties often boast beautiful gardens and scenic views.
Can I find long-stay vacation rentals in Winchester?
A long-stay vacation 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, with a total of 24 options to choose from. Travellers can expect a variety of amenities within these rentals, such as fully equipped kitchens, comfortable living spaces, and gardens or outdoor areas where pets can enjoy some fresh air. Many properties are designed with families in mind, often featuring multiple bedrooms and spacious layouts.
Are there any remote work vacation rentals in Winchester?
In Winchester, there is a good selection of remote work vacation rentals available, with around 57 properties suiting those needing a work-friendly environment. The city, steeped in history and charm, offers various accommodations that provide amenities specifically designed for remote work. Travellers can expect properties equipped with high-speed Wi-Fi, dedicated desks, and comfortable office chairs, ensuring a productive workspace. Many rentals also feature laptop workspaces and safes for added convenience and security. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winchester vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation 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 vacation rental?
The best time to visit Winchester for a vacation rental is during September, when the bustling summer crowds begin to ease. This month strikes a lovely balance, offering pleasant weather and a vibrant atmosphere without the peak tourist rush. With temperatures typically ranging from 15 to 20 degrees Celsius, September is ideal for leisurely strolls through the city's historic streets and lush parks.

The peak season in Winchester runs from July to September, attracting visitors eager to explore its rich history, including the iconic Winchester Cathedral and the medieval Great Hall. During these months, you can enjoy various outdoor events and festivals, making it an exciting time to experience the local culture.

For those seeking a more budget-friendly option, May is a fantastic choice. This month showcases the beauty of Winchester in spring, with blooming gardens and mild temperatures. While you may encounter fewer tourists, you'll still have access to the city's captivating sights and attractions, allowing for a more relaxed exploration.
How early should I book a Winchester vacation rental?
Book your Winchester vacation 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 vacation 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 engage in a rich tapestry of history and culture. The iconic Winchester Cathedral, with its stunning Gothic architecture, is a must-visit and often features vacation rentals nearby that offer convenient access to this landmark. Just a short stroll away, the Great Hall houses the legendary Round Table, adding to the historical allure of the city.

For those interested in outdoor pursuits, the picturesque River Itchen runs through the city, providing scenic walks and opportunities for fishing. The charming streets of the city centre, such as those around the High Street, are lined with quaint shops, cafes, and restaurants, making it a delightful area to explore while staying in the vicinity.
Can I change or cancel my Winchester home rental booking on Vrbo?
To find Winchester vacation 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 vacation 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.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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