Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

Teschemakers Resort

Teschemakers Resort
3.0 star property
Teschemakers
9.4 out of 10, Exceptional, (10 reviews)
"Very nice and quiet!"
Australia
Jawid
The price is NZ$296
includes taxes & fees
3 Apr - 4 Apr
Teschemakers Resort

Historic School in rural Oamaru with farm animals and outdoor baths

Historic School in rural Oamaru with farm animals and outdoor baths
Oamaru
10.0 out of 10, Exceptional, (24 reviews)
"Lovely hosts and fabulous house"
New Zealand
Lisa N.
The price is NZ$260
includes taxes & fees
13 Apr - 14 Apr
Historic School in rural Oamaru with farm animals and outdoor baths

Cosy Dell Tiny House

Cosy Dell Tiny House
Herbert
10.0 out of 10, Exceptional, (4 reviews)
"Very peaceful, well appointed with excellent hosts."
Australia
David
The price is NZ$209
includes taxes & fees
8 Apr - 9 Apr
Cosy Dell Tiny House

Sea Breeze Apartment - Kakanui

Sea Breeze Apartment - Kakanui
Kakanui
9.6 out of 10, Exceptional, (10 reviews)
"Gorgeous property close to the sea! "
New Zealand
Aoife W.
The price is NZ$389
includes taxes & fees
8 Apr - 9 Apr
Sea Breeze Apartment - Kakanui

Little Sweetie in the Heart of Old Oamaru

Little Sweetie in the Heart of Old Oamaru
South Hill
10.0 out of 10, Exceptional, (54 reviews)
"Beautiful property "
United Kingdom
Sara
The price is NZ$320
includes taxes & fees
16 Apr - 17 Apr
Little Sweetie in the Heart of Old Oamaru

Top of Tyne - Peace, Comfort & Local Connection

Top of Tyne - Peace, Comfort & Local Connection
South Hill
10.0 out of 10, Exceptional, (1 review)
The price is NZ$389
includes taxes & fees
7 Apr - 8 Apr
Top of Tyne - Peace, Comfort & Local Connection

Breathtaking sea view house

Breathtaking sea view house
Oamaru North
9.8 out of 10, Exceptional, (70 reviews)
"Wonderful property for our large family group. The view is breathtaking. Stargazing on a clear night was great."
United States
Barb T.
The price is NZ$554
includes taxes & fees
8 Apr - 9 Apr
Breathtaking sea view house

180 degrees sea view

180 degrees sea view
Oamaru North
9.6 out of 10, Exceptional, (10 reviews)
"Fantastic location looking over Oamaru. The house is very clean and the beds are very comfortable. The house has great heating and is very comfortable. Would stay again!"
Australia
Oliver
The price is NZ$375
includes taxes & fees
1 Apr - 2 Apr
180 degrees sea view

Exquisite Luxury Property with Stunning Views

Exquisite Luxury Property with Stunning Views
South Hill
10.0 out of 10, Exceptional, (5 reviews)
"Good location well stylish living"
Australia
Jay
The price is NZ$1,344
includes taxes & fees
1 May - 2 May
Exquisite Luxury Property with Stunning Views

Family-Fun Villa, Moonrise & Sunrise! Kids' Slide Bed! Ocean & Town Views 5-Beds

Family-Fun Villa, Moonrise & Sunrise! Kids' Slide Bed! Ocean & Town Views 5-Beds
Oamaru North
The price is NZ$1,409
includes taxes & fees
7 Apr - 8 Apr
Family-Fun Villa, Moonrise & Sunrise! Kids' Slide Bed! Ocean & Town Views 5-Beds
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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Top Windsor Hotel Reviews

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as NZ$209 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Beautiful ocean view from this lovely holiday home: This holiday home rental outside of Windsor is located on the beach, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Oamaru Harbour. In the wider area, you’ll find North Otago Museum and Alps 2 Ocean Cycle Trail.

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.