Windsor Vacation Rentals

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Vacation Rentals in Windsor

Stone Cottage in Central Oamaru (No Extra Cleaning Fee)
3 bedrooms, iron/ironing board, WiFi, bed sheets

Stone Cottage in Central Oamaru (No Extra Cleaning Fee)

8.8 out of 10, Excellent, (42)
"Lovely wee cottage walking distance to the town centre . Lovely and quiet at night with comfortable beds . "
$133 nightly
The price is $150
Oct 12 - Oct 13
Total with taxes and fees
Stone Cottage in Central Oamaru (No Extra Cleaning Fee)
Teschemakers Resort
Banquet hall

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"
$71 nightly
The price is $81
Oct 5 - Oct 6
Total with taxes and fees
Teschemakers Resort
Watch the weather roll in along the coast with sea views from every room.
On the beach, sun loungers

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

9.2 out of 10, Wonderful, (76)
"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."
$181 nightly
The price is $206
Oct 5 - Oct 6
Total with taxes and fees
Watch the weather roll in along the coast with sea views from every room.
Peaceful cottage in private garden setting.
Property grounds

Peaceful cottage in private garden setting.

10.0 out of 10, Exceptional, (4)
"Very clean , warm and quiet . "
$134 nightly
The price is $151
Oct 6 - Oct 7
Total with taxes and fees
Peaceful cottage in private garden setting.
The Sun set Cottage 5min from Oamaru or Kakanui
Property grounds

The Sun set Cottage 5min from Oamaru or Kakanui

10.0 out of 10, Exceptional, (51)
"Lovely place will be back"
The Sun set Cottage 5min from Oamaru or Kakanui
Comfortable family home with beautiful wild gardens to enjoy.
Property grounds

Comfortable family home with beautiful wild gardens to enjoy.

8.0 out of 10, Very Good, (1)
"Internet reception very poor/no instruction for tv combined with poor internet reception we were unable to view any programs "
Comfortable family home with beautiful wild gardens to enjoy.
Life by the sea! Enjoy tranquil views and all-day sun.
Fridge, microwave, oven, stovetop

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

Life by the sea! Enjoy tranquil views and all-day sun.
Big space in a great location
Fridge, microwave, oven, stovetop

Big space in a great location

10.0 out of 10, Exceptional, (1)
"Very tidy, everything we needed and an excellent location. Very good value for money "
Big space in a great location
Kakanui Coastal Retreat
Smart TV, fireplace

Kakanui Coastal Retreat

$242 nightly
The price is $274
Oct 10 - Oct 11
Total with taxes and fees
Kakanui Coastal Retreat
Beautiful ocean view from this lovely holiday home
On the beach

Beautiful ocean view from this lovely holiday home

9.6 out of 10, Exceptional, (251)
"Great place to stay. Easy checkin"
Beautiful ocean view from this lovely holiday home
Sea Breeze Apartment - Kakanui
Beach

Sea Breeze Apartment - Kakanui

9.4 out of 10, Exceptional, (6)
"Well located property, clean, modern, well appointed, includes breakfast"
$161 nightly
The price is $183
Oct 10 - Oct 11
Total with taxes and fees
Sea Breeze Apartment - Kakanui
Highlands on Homestead -Tranquil rural property only minutes from town
Property grounds

Highlands on Homestead -Tranquil rural property only minutes from town

10.0 out of 10, Exceptional, (68)
"Has everything you need, including iron/ ironing board. Bfast items offered. We were able to bring our labrador. Lovely spot. "
Highlands on Homestead -Tranquil rural property only minutes from town
Kakanui Cube
On the beach

Kakanui Cube

9.8 out of 10, Exceptional, (33)
"Great place , had a great time tks"
$253 nightly
The price is $287
Oct 14 - Oct 15
Total with taxes and fees
Kakanui Cube
Breathtaking sea view house
Interior

Breathtaking sea view house

9.8 out of 10, Exceptional, (61)
"Beautiful views, spectacular sunrises, and lovely house. Very clean and tidy. Couldnt fault it in any way. Would stay again. "
$228 nightly
The price is $259
Oct 15 - Oct 16
Total with taxes and fees
Breathtaking sea view house
Little Sweetie in the Heart of Old Oamaru
Fridge, microwave, oven, stovetop

Little Sweetie in the Heart of Old Oamaru

10.0 out of 10, Exceptional, (43)
"It is a gorgeous property. Great space, clean and great views."
$164 nightly
The price is $186
Oct 10 - Oct 11
Total with taxes and fees
Little Sweetie in the Heart of Old Oamaru
Oamaru travel mates house
Property grounds

Oamaru travel mates house

5.4 out of 10, (3)
"Clear information about the property/accommodation. Help and not booking through another company, VRBO. The accommodation absolutely did not meet our expectations! Instead of 3 nights, we only stayed one night. We thought we were renting the entire house and not just one room. One toilet/shower for 9-10 people!!!"
$95 nightly
The price is $107
Oct 6 - Oct 7
Total with taxes and fees
Oamaru travel mates house
Cosy Dell by Tiny Away
Exterior

Cosy Dell by Tiny Away

10.0 out of 10, Exceptional, (3)
"Very peaceful, well appointed with excellent hosts."
$180 nightly
The price is $180
Oct 6 - Oct 7
Total with taxes and fees
Cosy Dell by Tiny Away
Forest Hill Farm by Tiny Away
Outdoor dining

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...
$136 nightly
The price is $136
Oct 6 - Oct 7
Total with taxes and fees
Forest Hill Farm by Tiny Away
Exquisite Luxury Property with Stunning Views
Outdoor dining

Exquisite Luxury Property with Stunning Views

10.0 out of 10, Exceptional, (4)
"Good location well stylish living"
$787 nightly
The price is $891
Oct 6 - Oct 7
Total with taxes and fees
Exquisite Luxury Property with Stunning Views
Historic School in rural Oamaru with farm animals and outdoor baths
Exterior

Historic School in rural Oamaru with farm animals and outdoor baths

10.0 out of 10, Exceptional, (22)
"This place is amazing we loved our stay and didn’t want to leave"
$151 nightly
The price is $151
Oct 6 - Oct 7
Total with taxes and fees
Historic School in rural Oamaru with farm animals and outdoor baths
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

Poshtel

Poshtel

10/10 Excellent
"Great room and lovely friendly team on reception! Will go back again ☺️"
Vanessa 1-night trip
Posted 2 days ago
Poshtel

Find out more about Windsor

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $81 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation 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 vacation.

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, there are vacation rentals near well known sights in Windsor, or you can choose a more remote option if you'd like a relaxing place to stay.

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

Stone Cottage in Central Oamaru (No Extra Cleaning Fee): This vacation home rental near Windsor is located in the city center 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 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 larger area, you’ll find Oamaru Gardens and Steampunk HQ.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can reserve for several days or more in Windsor. Vacation 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 sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering.