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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  • All the privacy of home

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

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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)
  • Botanic Gardens (15.2 mi / 24.4 km)
  • Washdyke Lagoon Wildlife Refuge (12.5 mi / 20.1 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

How much does it cost to rent a holiday home in Winchester?
A range of things can affect what you'll pay for your holiday home in Winchester, including the season, type of property and length of stay. But, all Stayz homes have something in common — incredible value. Just enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Winchester?
The average price for a holiday home close to the beach in Winchester will depend on when you're going and the size and type of property you're looking for. You can find prices easily and quickly on Stayz by entering your preferred travel dates. Then use our filter tool to choose the number of bedrooms and amenities that you require, like WiFi, air conditioning and a hot tub.
What are the top attractions for families in Winchester?
Keep the kids amused at these top family-friendly attractions in Winchester:
  • Geraldine Vintage Car and Machinery Museum
  • Vintage Car & Machinery Museum
  • Geraldine Observatory
How old do you have to be to rent a holiday home in Winchester?
The minimum age allowed can differ between properties on Stayz, so look at the rules of the holiday home in Winchester you're interested in. But in general, it's 16, 18 or 21.
How long can I rent a holiday home in Winchester for?
The amount of time you can book a Winchester holiday home for depends on the property. Simply put in your dates of travel to find available options offering extended stays. They have everything you need to make your extended holiday more comfortable and enjoyable, like kitchens and yards. Some Stayz holiday properties may also offer weekly or monthly discounts, so you can stay even longer for less.

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