Vacation rentals in Winchester

Struan Farm Retreat Geraldine

Beautiful native trees and birdsong surround your own peaceful, private, and quiet cottage and gardens. We have a star gazing area where you will be awed by the clear sky and see the Milky Way and all the constellations. Our Retreat Cottage is very well equipped with everything you need, including a 3 pin EV charging port. Your hosts, Drew and Sally, will meet you and show you around their small farm including cows, chickens and native birds, and browse the large vegetable gardens and orchard.

Fiery Peak Eco-Retreat with Stargazing & Hot Tub

* Luxury eco-friendly cabin set on the edge of forest with stunning views of the Four Peaks of South Canterbury - with a Noon "no rush" check out * King Bed with wood fire in open plan living room * Spring-fed plunge pool * Wood-fired hot tub - $70 for one night ($100 for 2) * Stunning dark sky stargazing. Daytrips to Tekapo, Mt Cook, Mt Sunday (Lord of the Rings, * 8kms from Geraldine for cafes/restaurants/museums * BBQ & couch on the covered verandah-birdsong, native birds flying overhead.

Stonebridge Guesthouse

Escape to our charming garden guesthouse, where tranquility marries perfectly with comfort. Nestled amongst lush greenery, overlooking a picturesque pond, Stonebridge guesthouse offers a peaceful retreat with modern amenities. Situated within the village of Geraldine, the cottage offers the best of both worlds… rurally tucked away but still close enough to town. Whether you're seeking a weekend getaway or a longer stay, our garden cottage is the perfect oasis for relaxation and rejuvenation

Peaceful tiny house with sweeping mountain views

This rustic, beautiful and comfortable tiny house, just 1 km from the centre of Fairlie, is surrounded by farms and boasts stunning views of the Two Thumb Range (Mt Dobson). The house will feel like home the moment you arrive! Try the famous Fairlie pies while visiting! Mt Dobson skifields are about 15 min away. Lake Tekapo - with its hot springs and other tourist attractions - is just a half hour drive away. Escape your stresses and soak in the farm and mountain views from the deck.

Xantippe Downs - Separate unit in Peaceful Setting

Separate studio is ideal for couples, solo travelers or business person. Located not far from the town centre but has a rural feel, giving you peace and quiet. Queen bed, fridge, toaster, tea/coffee facilities, continental breakfast and Wifi (now with Satellite giving good connection) A nice comfortable and cosy place to stay. Geraldine is a vibrant town offering boutique shopping, cafes and numerous outdoor activities. Access is via a Lock Box, giving you total control.

Arle's Nook

Arle’s Nook is just that, it’s a little nook nestled amongst our slice of paradise. From comfort & warmth of a newly built cabin you over look our small farm and have some amazing mountain views and some equally amazing sunsets. Peace & tranquility take over as you are far enough out of town, while actually only being 2 minutes from Temuka's Town Centre, 15 minutes from Timaru's Caroline Bay and Town Centres Cafes and Shops and 8 minutes from Fonterra's Clandeboye Site.

Oakham Cottage - English style gardens, Geraldine.

Our lovely 2-bedroom cottage is situated on a large section surrounded by beautiful English style gardens. The gardens are well established, have beautiful hedges, flower beds and wildlife. We have a private outdoor area which has a BBQ and outdoor furniture so you can enjoy comfortable outdoor living. The cottage was redecorated in July 2025. The cottage has a heat pump. It's an easy a 1-minute car journey into the centre of Geraldine, or a 15-minute flat walk.

Self contained bedsit.

Sunny, self contained rooms including separate kitchenette & bathroom with access to shared deck & garden. Own access, twin single beds & free ON STREET PARKING. No extra cleaning fee. I personally clean thoroughly and sanitise all hard surfaces, but expect you to clean, dry & put stuff away that you use where you found them. Bus is Myway, which you book & it picks to up close by or 25-30 minutes walk to town centre, 5 min drive. Supermarket 10 mins walk.

Modern Apartment, Great Location

Start the day with the morning sun in our modern, spacious lower-level retreat with a separate entrance for your convenience. Enjoy a cozy queen bed with an electric blanket, a heat pump for your comfort, ensuite bathroom, and well-equipped kitchenette. Stay connected with WiFi and unwind with Netflix. Conveniently located just a 5-minute walk from Geraldine Village and with bush walks right across the road. Book now for a relaxing stay!

Timaru Central

Built in 1905, and converted to 2 apartments in the 1950's, we live in the other apartment. The apartment is located in Central Timaru, being 5 minutes walk from the central business area and the Caroline Bay beach and facilities. Fully self contained, it suits a range of requirements from a single person staying overnight, to a family wanting a longer stay. Caroline Bay is home to a local small 'Little Blue Penguin' colony.

Country Cabin

The warm and cosy cabin is a self contained unit detached from the main house, with BBQ, private deck and restful native garden. You will have your own access/key and off road parking. Our place is great for couples. On navman route, we are 2 hours from Christchurch and 4 hours to Queenstown. Only 1 hour from Mt Hutt ski field and 1 hour from Mt Dobson ski field. Aoraki Mount Cook is 2 hours distance and Tekapo is 1 hour.

Beauly Farm Stay Cottage-Cute & Cosy

Beauly Farm Cottage is one of those special places to stay if you want something that is bespoke and definitely not mainstream accommodation. Set in beautiful established grounds, this self contained cottage is perfect for a couple wanting the privacy, peace and tranquility of their own space in the country. Only minutes to Geraldine. Close to quaint Woodbury Village, Beauly Cottage has stunning views to Mount Peel.