Winchester holiday rentals

We found 17 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Winchester that are perfect for your trip. Whether you're staying in a holiday rental with your children and pets or just with friends, you'll have the amenities that you expect and more, which might include Wi-Fi and a pool. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

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  • More quality time

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  • 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

  • Rich outdoor experiences: Enjoy scenic forest walks and family-friendly excursions in nature.
  • Cultural attractions: Explore local transport and history museums that highlight the region’s heritage.
  • Eco-friendly holiday vibe: Embrace a sustainable, natural retreat perfect for families and adventurers.
  • Charming rural ambience: Experience warm local hospitality in a picturesque setting.
  • Variety of stays: Choose from private holiday homes, apartments, and cottages for a comfortable visit.

Popular types of accommodation in Winchester

If you are unsure what type of accommodation you can expect in Winchester, we have you covered. These are the most popular types of accommodation here: Private Holiday Homes, Apartments, and Cottages. Enjoy rent in Winchester with a range of Winchester holiday rentals that offer Winchester holiday accommodation and Winchester holiday homes, all set amidst the unique attractions, landmarks, and experiences found in Winchester, Canterbury, New Zealand.

  • Private Holiday Homes: Leading the way in popularity, these spacious residences offer a home-like atmosphere, ideal for families or groups seeking comfort and privacy during their stay in Winchester.
  • Apartments: A close second, apartments provide a convenient and modern option for those looking for self-catering facilities in the heart of the town.
  • Cottages: These quaint dwellings are perfect for a charming getaway, offering a cosy ambiance for couples or small families.
  • Chalets: For a unique experience, chalets present a rustic option, often nestled in picturesque surroundings, ideal for nature enthusiasts.
  • Villas: Lastly, villas offer a luxurious retreat with ample space, perfect for those seeking a lavish holiday experience.**

Top attractions near Winchester

Winchester in Canterbury, New Zealand offers a delightful mix of outdoor and cultural experiences. Families and adventure seekers alike can explore transport and history museums, as well as enjoy the natural beauty of nearby forests. This charming city is ideal for eco-friendly holidays with a rich blend of culture and adventure, ensuring a memorable visit in a stunning, nature-filled setting.

Things to do recommended for couples

Winchester offers a charming getaway for couples. Explore the historic streets hand in hand, visit the stunning Winchester Cathedral, and enjoy a leisurely picnic in the serene gardens. Don’t miss a romantic dinner at a local restaurant, where you can savour exquisite cuisine and fine wine together.

Things to do recommended for families

Families visiting Winchester, New Zealand, can explore the stunning landscapes at the local parks, enjoy a fun-filled day at the Winchester Golf Club's mini-golf, and discover the fascinating wildlife at nearby nature reserves, ensuring an unforgettable experience for all ages.

Things to do recommended for groups

Groups in Winchester can immerse themselves in local history with guided walks exploring ancient landmarks, savour traditional fare at cosy pubs, and enjoy scenic countryside picnics, all offering a genuine taste of British charm.

*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 travelling in a group, as a family, with your pets, or seeking extended stays, ensure you apply the appropriate filters. 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, Stayz allows you to filter for all these options and more.
  • Traveling to Winchester with young kids: Travelling with young children can present its own set of challenges. It’s important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Winchester: For many, a family holiday is not truly complete without their four-legged companion. If this resonates with you, take a look at Stayz properties that welcome pets. Most of these 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 holiday rentals offering savings 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 include amenities such as a parking space, a lovely kitchen, or a private pool in your search criteria as well.

Where to stay near Winchester

Winchester, a charming suburb in Canterbury, New Zealand, is perfect for outdoor and eco-friendly family holidays. Visitors can immerse themselves in the breathtaking scenery and enjoy friendly local vibes. With ample opportunities for excursions, families can explore the natural beauty of the area while experiencing the warm atmosphere of this rural settlement. Winchester offers a variety of activities that cater to all ages, making it an ideal destination for a memorable family getaway.

  • Geraldine: Geraldine is a charming suburb located 11km from Winchester. This picturesque locale is celebrated for its outdoor pursuits, scenic beauty and a romantic atmosphere. Visitors can enjoy a variety of experiences including shopping in local retail areas, recreational activities and seasonal skiing. The area is further enhanced by its proximity to stunning natural landmarks such as a serene lake, a majestic mountain and a national state park, making it an ideal retreat for those in search of scenic landscapes and tranquil adventures.
  • Temuka: Temuka, positioned 6km from Winchester, offers a delightful blend of outdoor enjoyment, scenic vistas and romantic experiences. This suburb is noted for its rejuvenating body treatments and spa experiences, perfect for unwinding. Its attractions include a picturesque lake, a history museum that delves into the local heritage, and a nearby mountain that adds to the region’s natural allure, providing a well-rounded travel experience.
  • Orari: Orari is a vibrant suburb also located 6km from Winchester, known for its appeal to those seeking outdoor excitement, adventure and captivating scenery. The area invites visitors to indulge in relaxing body treatments while also offering access to natural wonders such as a towering mountain, a national state park and a tranquil lake. This combination of amenities and natural beauty makes Orari a compelling destination for travellers looking to explore the great outdoors.

Booking with Stayz is simple

Looking to save money on your next holiday? Try being flexible with your travel dates as prices can vary. Additionally, booking a longer stay can often lead to significant savings. To find the ideal Stayz property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz’s Trip Board offers a user-friendly platform for you to plan new journeys, continue from where you last left off, or manage your travel arrangements. Here, you can easily view properties you’ve saved or booked, organised into categories such as Potential, Upcoming, or Current Trips. To get started with Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

The cosy city of Winchester awaits you

The gardens and other outdoor surroundings create an inviting atmosphere in Winchester. Revered for its camping, cafes and spas, this city is both walkable and welcoming. 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 hoping to discover top things to see and do in the area? Venture out of your cosy holiday rental and check out everything that makes Winchester a fun place to get away to. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Pleasant Valley Daffodils (8.7 mi / 14 km)
  • Jacks Point Surfspot (17.1 mi / 27.5 km)

Exploring the natural features in Winchester

Whether you're an active traveller or just want to take in the scenery, Winchester is a great place to get outside. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Ashbury Park (14 mi / 22.5 km)
  • Caroline Bay Beach (14.2 mi / 22.9 km)
  • Talbot Forest Scenic Reserve (7.7 mi / 12.4 km)
  • Washdyke Lagoon Wildlife Refuge (12.5 mi / 20.1 km)
  • Botanical Gardens (15.7 mi / 25.3 km)
  • Dashing Rocks Beach (13.4 mi / 21.6 km)

Transport to and around Winchester

Fly into Timaru (TIU-Richard Pearse), the closest airport, located 9.1 mi (14.6 km) from the city centre.

Frequently asked questions

When is the best time to visit Winchester for a holiday rental?
The best time to visit Winchester, Canterbury, is during the peak season from February to April, when the region comes alive with vibrant outdoor activities and stunning landscapes. March, in particular, is a standout month, as the weather is pleasantly mild, with temperatures ranging from 10 to 20 degrees Celsius, creating ideal conditions for exploration and adventure.During this period, visitors can enjoy the picturesque scenery, with lush greenery and blooming flowers enhancing the charm of the area. The nearby Banks Peninsula offers breathtaking views and a variety of walking tracks, making it superb for those who appreciate outdoor activities such as hiking and sightseeing.For those looking for a more budget-friendly option, consider visiting in August. While this is the low season, it presents a unique opportunity to experience Winchester in a quieter, more serene atmosphere. The crisp winter air can be invigorating, and you may find the local cafés exceptionally welcoming after a day of exploring the stunning landscapes.Ultimately, your choice of when to visit Winchester will depend on whether you prefer the bustling energy of the peak season with its numerous outdoor activities or the tranquil beauty of the winter months.
What are the top attractions in Winchester?
In Winchester, Canterbury, New Zealand, visitors can enjoy a serene rural atmosphere while exploring several charming attractions. The local area is known for its picturesque landscapes and proximity to the Waimakariri River, ideal for outdoor activities such as fishing and kayaking. The nearby Rakaia Gorge offers stunning views and walking tracks that showcase the region's natural beauty.For those interested in local history, the Winchester District Museum provides insights into the area's heritage and culture. Additionally, the stunning Ashburton Lakes are not far away, offering a wonderful spot for picnics, hiking, and enjoying the scenic surroundings.The vibrant town of Ashburton, located a short drive away, boasts a variety of shops, cafes, and parks, making it an excellent day trip destination for those staying in Winchester.
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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