Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
Hut in Danseys Pass
4.96 out of 5 average rating, 115 reviews

Danseys Pass Lavender Farm Retreat (shepherds hut)

Enjoy a unique stay at our little Lavender Farm nestled in the Kakanui Ranges. Sitting adjacent to the main house, you'll find comfort in your self-contained shepherd's hut, complete with a private outdoor bath and shower. Take the mountain e-bikes for a tour around the surrounding countryside, jump into one of the waterholes on the property. At the end of the day, unwind in your private 4-person spa opposite the rustic wood-fired sauna, or simply relax by the outdoor fireplace under the stars.

Guest favorite
A stone archway features wooden double doors, standing open to reveal a pathway leading into a lush green space. Overhanging trees create a shaded entrance, inviting exploration into the secluded garden area beyond.
Cabin in Oamaru
4.81 out of 5 average rating, 506 reviews

Bookbinders's Retreat

Located in Oamaru, this beautifully restored, cosy and warm Cabin is the perfect place to base yourself at while you explore the Otago region. Bookbinder's Retreat is small self-contained studio, situated adjacent to the main house. Whilst in the town, the property has a rural outlook over the Public Gardens, and a secluded feel. I have enjoyed creating the space on a small budget over a long time. Travellers seem to appreciate the craftsman like quirkiness of the space which reflects the town.

Top guest favorite
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, 248 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 favorite
Farm stay in Oamaru
4.94 out of 5 average rating, 352 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.

Guest favorite
A spacious garden surrounds a red brick house, showcasing well-maintained flower beds and lush greenery. A serene landscape is featured with rolling hills in the background, while a gravel driveway leads to the residence, conveying a peaceful countryside atmosphere.
Farm stay in Oamaru
4.95 out of 5 average rating, 146 reviews

Self-contained apartment - Oamaru outskirts

STAY AT THE GROVE. Stunning views of the North Otago lowlands awaits in our warm self-contained apartment. Features open-plan kitchen & living, private bathroom and bedroom with a luxurious king-size bed overlooking the garden and views. Beautiful setting with private entrance and plenty of parking. Make yourself at home, explore the area and rest in our flat furnished for comfort. Located on the bottom level of our family home just 10 minutes drive inland from Oamaru.

Top guest favorite
A modern loft apartment is nestled among lush greenery. A large deck extends from the structure, offering stunning views of the surrounding area, including glimpses of the sea. The building features clean lines and a contrasting dark exterior, blending naturally with the landscape.
Loft in Oamaru
4.98 out of 5 average rating, 873 reviews

Steampunk Loft - stay uniquely Oamaru this summer

*****Treat yourself to a quintessential Oamaru experience ***** Located close to town with stunning views over the basilica to the sea. Styled in a futuristic genre set in an 1800’s world, our Steampunk loft apartment features a mix of recycled materials remodeled for today’s purpose. This is an exceptional space to indulge your inner steampunk fantasy while enjoying a warm modern industrial space with all the luxuries you deserve for your stay in Oamaru.

Top guest favorite
Farm stay in Oamaru
4.95 out of 5 average rating, 808 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.

Top guest favorite
Farm stay in Oamaru
4.98 out of 5 average rating, 236 reviews

Shepherd’s Rest - outdoor bath, alpaca & sheep

The Shepherd's Rest is a Shepherds Hut and glamping experience. The hut is situated on a 300 acre bull beef farm and approx a 10 minute drive to central Oamaru. Unwind in the outdoor bathtub (gas heated). The 3 alpaca & pet sheep are your friendly neighbours. 4pm Farm Tour for additional fee. The country location is the perfect place to relax, star gaze, enjoy the scenery, birdsong & farm sounds. It’s a great base to explore Oamaru & the Waitaki area.

Top guest favorite
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
4.94 out of 5 average rating, 170 reviews

Woolshed Lodge Farmstay Kurow

Woolshed Lodge Farmstay. Enjoy mountain & forest views and farm animals Modern space to relax & enjoy a rural experience. Great stars on clear nights. The Lodge offers extra experiences, aWoodfired Hot Tub in a forest grove, Infared sauna, delicious meals and local wines. When you book you get the whole Lodge to yourself. We have a tiny house on the property too. Tiny house guests use a separate bathroom by the Lodge's back door. WiFi on request

Guest favorite
The cottage presents a charming exterior with a light grey facade and a white gabled roof. Smooth stone walls and young trees adorn the front yard. Large windows allow natural light to fill the interior, enhancing the inviting appearance of the home.
Home in Oamaru
4.89 out of 5 average rating, 127 reviews

Best Location in Town!

Our cottage is the closest Airbnb to the blue penguin colony! You will love the sea views & the 2 minute walk to the Victorian Precinct, Harbour, playground, shops & cafes. We have 2 spacious bedrooms with comfortable king beds & fresh white linen. There is new fully equipped kitchen, free high speed WIFI & free parking outside the house. Our house is a gorgeous cottage with fresh, modern decor & everything you need for your stay in Oamaru.

Top guest favorite
Farm stay in Oamaru
4.9 out of 5 average rating, 267 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.

Top guest favorite
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, 338 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.

Popular amenities for Windsor vacation rentals

  1. Airbnb
  2. New Zealand
  3. Otago
  4. Windsor