Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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A small outdoor patio area features a glass table surrounded by wooden chairs with floral cushions. A wide bench is visible against the wall. Sunlight streams onto the wooden deck, creating a bright and inviting space.
Guest suite in Oamaru
4.73 out of 5 average rating, 138 reviews

Guest Suite: Private entry own kitchen & bathroom

Private, spacious self-contained guest suite with own entry, on a quiet street in Oamaru. You will have your own kitchen and bathroom as well as a washing machine, dishwasher, queen-size bed and free wifi.. Everything you need for a comfy stay to enjoy our picturesque town. On sunny days you can sit out on the deck chairs with your preferred drink or down on the bench in the small garden. If you are here in the summer you will be able to pick some strawberries - we planted them for our guests!

Top guest favourite
A view of Kowhai Cottage is presented, surrounded by lush greenery and mature trees. The cottage's simple design is complemented by the grassy landscape, with a gravelled private area visible nearby. The Old Manse can be seen in the background, adding to the scenic atmosphere.
Guesthouse in Herbert
4.99 out of 5 average rating, 234 reviews

Kowhai Cottage, Herbert, Presbyterian Old Manse

‘Kowhai Cottage’ is set in the mature grounds of the 1867 grade II listed Old Manse, (Lawson, R.A .architect). Ideal for a weekend break, overnight or holiday to visit the Waitaki district with all of it’s unique attractions Victorian Oamaru; Moeraki boulders 10mins south; Dunedin City an hour’s drive; turquoise lakes 90 minutes west with Duntroon, Alps2Ocean tracks and Elephant Rocks enroute. Hosts Susie & Bob live onsite ensuring your stay cosy & memorable. Not suitable for infants/ kids.

Guest favourite
The exterior of Woolshed Lodge is showcased against a clear blue sky. The modern structure features large windows and a spacious deck area, surrounded by native plants and greenery, enhancing the rural setting. Outdoor seating is visible, creating a welcoming space for relaxation.
Farm stay in Kurow
4.93 out of 5 average rating, 148 reviews

Kiwi Woolshed Lodge. Farmstay Kurow

Woolshed Lodge farmstay. Enjoy mountain & forest views. Idyllic rural setting. Modern space to relax & enjoy a rural experience in a unique grand design. Explore the Waitaki & Lakes Minutes to Kurow center Delicious meals available, local wines. Enjoy Woodfired Hot Tub in forest grove. Massage center right next door. Area offers great hunting/fishing/hiking/biking/lakes. When you book you get the whole place to yourself. Spare bathroom by back door maybe used by others. WiFi on request

Top guest favourite
A Highland cow with long, shaggy fur and prominent horns stands in a grassy area, accompanied by a small dog wearing a collar. The backdrop features trees and a clear blue sky, creating a peaceful rural setting.
Farm stay in Oamaru
4.94 out of 5 average rating, 338 reviews

Highlands on Homestead a stone’s throw from town.

Spacious, comfortable and modern 1 bedroom unit with ensuite. A 2nd DETACHED room as an additional bedroom is available (see photo, fees apply) The cottage is equipped with microwave, stove top, toaster, kettle and basic utensils to prepare a simple meal. Private, delightful garden & decks facing the sun. Outdoor seating provided. Your well behaved, house trained dog is welcome to stay. Please let me know if your travelling with your furry friend and/or you require the 2nd bedroom.

Top guest favourite
A modern home features a mix of sharp angles and clean lines, with a combination of grey and beige cladding. A spacious driveway leads to a double garage, while a secure gate provides access to the main entrance. The address '37 Eden St' is prominently displayed.
Bungalow in Oamaru
4.93 out of 5 average rating, 194 reviews

"Excellence on Eden" designed for comfort

An elegant European-inspired home located in Oamaru-North Otago's jewel in the crown. This high quality, 6 month old, superb home has everything you need for a fantastic holiday in Oamaru & surrounds. Excellence on Eden is fully secure wth offstreet internal access garage. Perfect position for walking distance to the main street, wide choice of retail outlets, incl artisan craftspeople; cafes; home of multi-award winning Whitestone Cheeses; Oamaru Blue Penguin colony.

Guest favourite
A spacious modular sofa is positioned in the lounge area, adorned with decorative pillows and a soft throw blanket. In the background, a California King four-poster bed is visible, draped in rich fabrics, offering a glimpse of the elegant sleeping space.
Place to stay in Oamaru
4.97 out of 5 average rating, 303 reviews

Marvel at this stunning historic chapel renovation

We would be delighted for you to book our unique space and experience a getaway of pure indulgence in our stunning Chapel renovation in the heart of Oamaru. Expect to be amazed as you open the door into the main Chapel building and encounter the seven metre high ornate ceiling, beautiful stained glass windows and original alter. The 125m2 space is full of all the luxuries of a new modern day appartment and is exclusively yours to enjoy during your stay.

Top guest favourite
A tranquil bedroom features a wrought-iron bed dressed in soft linens, complemented by a wooden nightstand and a decorative mirror. A vintage chair and fresh flowers add charm. Light enters through a large window, framing views of the surrounding garden.
Farm stay in Oamaru
4.95 out of 5 average rating, 777 reviews

Cape Wanbrow Cottage

This is an entire apartment with views to the Ocean. It is cosy and quiet and only 5 minutes from Oamaru but set in a beautiful rural environment. A new kitchen, a cosy loungeroom and private courtyard with barbeque and separate entrance. Tea, coffee, milk and basic supplies in the pantry, homemade bread and a sample of our own honey . Breakfast cereals provided . You will love it. A pleasant garden and views top it all off....while being handy to town.

Guest favourite
The exterior of a modern tiny home is displayed, featuring a red wooden facade and large glass windows. A deck with outdoor seating is visible, along with a covered hot tub. Surrounding greenery complements the home, enhancing its rural setting.
Farm stay in Oamaru
4.88 out of 5 average rating, 213 reviews

Buckley’s Retreat

We offer this unique tiny home with fantastic Ocean views. You can wake to the sunrise and watch the sunset at night all from your bed. We offer continental breakfast. Which includes eggs if the hens are laying. Outdoor spa, Complementary snacks and beverages. You may also bring your dog. 5mins drive to the centre of town. But have restaurants and grocery shops near by. Off street parking also. Just on the town boundary with a rural feel.

Guest favourite
A modern studio with a sleek exterior is framed by surrounding greenery. The entrance features a small patio with two chairs and a table, inviting outdoor relaxation. Large windows allow for natural light to brighten the interior, which overlooks a tranquil rural setting.
Guesthouse in Oamaru
4.85 out of 5 average rating, 1,178 reviews

Sunshine studio

This studio is set in a beautiful rural setting just a couple of mins from CBD. It has a fully made comfy king bed & a pull out double bed from the sofa if needed. Linen included. Tea & coffee facilities in a small kitchenette, kitchen sink & bbq area outside, as well as a flat screen TV, DVD player, Freeview & washing machine. There are many animals, including goats, chickens, cows, pigs, rabbits, alpacas, ducks & birds to enjoy

Top guest favourite
A view of the calm harbor featuring numerous boats anchored in turquoise waters. The shoreline is lined with buildings and greenery, while a distant pier extends into the sea. The sky is a soft blue with gentle clouds above.
Apartment in Oamaru
4.94 out of 5 average rating, 310 reviews

Affordable On Arun - Close to everything!

Affordable On Arun is the 2nd closest accommodation to the Blue Penguin Colony and within 500m of restaurants and dining, Steampunk HQ and the Victorian Precinct. You’ll love the location and the all day sun . Located 1km from the penguin colony and 600 m from town with great views of the harbour, town and coastline, Affordable On Arun is a self contained studio / apartment located on the ground floor of our family home.

Guest favourite
A wooden deck offers expansive views of the ocean and coastline, framed by lush greenery and native trees. The horizon is clear under bright blue skies, with gentle slopes leading to the water's edge.
Home in Otago
4.94 out of 5 average rating, 365 reviews

Seascape

Nestled amongst the native trees, up on sunny South hill , hides a mid-century gem. Elevated over the garden with a deck that completes the house giving prime views of the ocean and sunrise. 2 minutes down the hill to the historic precinct filled with many delights including Blue Penguins ,bakery, coffee, art galleries and breweries.The East Coast golden sand beaches are a short ten minute drive away.

Top guest favourite
A quaint historic church conversion is set against a vibrant blue sky. The yellow exterior features decorative stonework, a tower, and a pointed arch window. Surrounding grassy areas enhance the tranquility of the property, complemented by distant hills that provide a scenic backdrop.
Place to stay in Otekaieke
4.99 out of 5 average rating, 194 reviews

Enchanting Otekaieke Church Waitaki Valley

This beautiful quaint church is situated in Otekaieke in the stunning Waitaki Valley. This accommodation has been tastefully converted to provide a warm and spacious retreat for one or two couples. Breakfast in the sunshine on the verandah overlooking farmland, the river valley and the Campbell Hills. This quiet and peaceful setting is situated only 35mins drive from the Victorian township of Oamaru.

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