Windsor Holiday Rentals

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Holiday Rentals in Windsor

Teschemakers Resort

3.0 star property
9.2 out of 10, Wonderful, (5)
"Very friendly host, and they make great chocolates right there on site. Would go again"
The price is NZ$141
includes taxes & fees
14 July - 15 July
Teschemakers Resort

Little Sweetie in the Heart of Old Oamaru

10.0 out of 10, Exceptional, (42)
"It is a gorgeous property. Great space, clean and great views."
The price is NZ$324
includes taxes & fees
15 July - 16 July
Little Sweetie in the Heart of Old Oamaru

Highlands on Homestead -Tranquil rural property only minutes from town

10.0 out of 10, Exceptional, (66)
"Jenny was great! She let me feed the animals and brought me a taste of local New Zealand fruit grown in her own backyard. The shower water pressure / heat is amazing! Such a relaxing visit and loved checking out Oamaru!"
The price is NZ$201
includes taxes & fees
14 July - 15 July
Highlands on Homestead -Tranquil rural property only minutes from town

Stone Cottage in Central Oamaru (No Extra Cleaning Fee)

8.8 out of 10, Excellent, (39)
"Lovely wee cottage walking distance to the town centre . Lovely and quiet at night with comfortable beds . "
The price is NZ$259
includes taxes & fees
14 July - 15 July
Stone Cottage in Central Oamaru (No Extra Cleaning Fee)

Kakanui Coastal Retreat

The price is NZ$477
includes taxes & fees
14 July - 15 July
Kakanui Coastal Retreat

Peaceful cottage in private garden setting.

10.0 out of 10, Exceptional, (2)
"On a family road trip around NZ from Aus in July. Stayed one night and loved the place. Great sized cottage, beautifully set up and well maintained. The surrounds are stunning with a lovely garden and so many little birds. Our host took great care of us with pre-lit pot belly and basics in the kitchen to see us right. I highly recommend this stay, it’s along the way and well worth it. "
The price is NZ$260
includes taxes & fees
14 July - 15 July
Peaceful cottage in private garden setting.

Watch the weather roll in along the coast with sea views from every room.

9.2 out of 10, Wonderful, (75)
"Excellent proximity to beach, wonderful views, plenty space for all generations, liked the open plan kitchen to living, we had a wondererful family xmas stay."
The price is NZ$335
includes taxes & fees
23 July - 24 July
Watch the weather roll in along the coast with sea views from every room.

Life by the sea! Enjoy tranquil views and all-day sun.

Life by the sea! Enjoy tranquil views and all-day sun.

Cosy Dell Tiny House

10.0 out of 10, Exceptional, (3)
"Very peaceful, well appointed with excellent hosts."
The price is NZ$271
includes taxes & fees
14 July - 15 July
Cosy Dell Tiny House

Beautiful ocean view from this lovely holiday home

9.6 out of 10, Exceptional, (249)
"Great place to stay. Easy checkin"
Beautiful ocean view from this lovely holiday home

Herbert Forest Retreat 15 min from Oamaru, H/tub and MTB tracks

9.4 out of 10, Exceptional, (3)
"Great stay. Warm,clean house with everything you need for a get away."
Herbert Forest Retreat 15 min from Oamaru, H/tub and MTB tracks

Forest Hill Farm by Tiny Away

6.0 out of 10, (1)
"The tiny home was perfectly fine, amenities were good, and the bunny watching from the window was very cute. However the email that arrived just prior to check-in that advised the use of earplugs to block the sound of traffic and trains…well it was good advice, but arrived a little too late. The perpetual falling of objects from the trees overhead onto the metal roof of the house all together with the train rumbling through and trucks thundering by, lead to a less than decent sleep. For the...
The price is NZ$207
includes taxes & fees
14 July - 15 July
Forest Hill Farm by Tiny Away

Sea Breeze Apartment - Kakanui

9.4 out of 10, Exceptional, (6)
"Well located property, clean, modern, well appointed, includes breakfast"
The price is NZ$308
includes taxes & fees
15 July - 16 July
Sea Breeze Apartment - Kakanui

Comfortable family home with beautiful wild gardens to enjoy.

Comfortable family home with beautiful wild gardens to enjoy.

180 degrees sea view

9.4 out of 10, Exceptional, (6)
"Clean, tidy, with nice king size beds"
The price is NZ$356
includes taxes & fees
16 July - 17 July
180 degrees sea view

Historic Cottage in rural Oamaru with farm animals and outdoor baths

10.0 out of 10, Exceptional, (22)
"Grouse as! Awesome hidden gem if you're wanting a quiet getaway far from the crowded tourist hotspots. "
The price is NZ$260
includes taxes & fees
14 July - 15 July
Historic Cottage in rural Oamaru with farm animals and outdoor baths

The Sun set Cottage 5min from Oamaru or Kakanui

10.0 out of 10, Exceptional, (49)
"Comfortable, clean and peaceful. Couldnt ask for more."
The Sun set Cottage 5min from Oamaru or Kakanui

Breathtaking sea view house

9.8 out of 10, Exceptional, (61)
"House has an amazing view. The 2 1/2 bathrooms were great for our larger group. Worked really well. "
The price is NZ$448
includes taxes & fees
14 July - 15 July
Breathtaking sea view house

Exquisite Luxury Property with Stunning Views

10.0 out of 10, Exceptional, (4)
"Good location well stylish living"
The price is NZ$1,532
includes taxes & fees
14 July - 15 July
Exquisite Luxury Property with Stunning Views

Cozy 2 Bedrooms Lavender Garden House at Oamaru, sweet as home!

10.0 out of 10, Exceptional, (3)
"It was right in the town centre , with free parking , so close to everything. Great place. "
Cozy 2 Bedrooms Lavender Garden House at Oamaru, sweet as home!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

Can I find holiday rentals in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Windsor has to offer?

Stone Cottage in Central Oamaru (No Extra Cleaning Fee): This holiday home rental outside of Windsor is located in the city centre, and has a garden, a selection of books and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What’s there to see and do in Windsor?

Explore the area and family-friendly sights such as Whitestone Cheese Factory, or get out into nature at a spot like Elephant Rocks. In the wider area, you’ll find Oamaru Gardens and Steampunk HQ.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.