Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In two months
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Jan 16 - Jan 18

Vacation Rentals in Windsor

Our top choices for Windsor vacation rentals

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."
The price is ￥15,566
￥30,613 total
includes taxes & fees
Sep 28 - Sep 29
Watch the weather roll in along the coast with sea views from every room.
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, (41)
"Lovely wee cottage walking distance to the town centre . Lovely and quiet at night with comfortable beds . "
The price is ￥17,036
￥22,360 total
includes taxes & fees
Sep 26 - Sep 27
Stone Cottage in Central Oamaru (No Extra Cleaning Fee)
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. "
The price is ￥21,793
￥38,725 total
includes taxes & fees
Sep 30 - Oct 1
Breathtaking sea view house
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"
The price is ￥10,001
￥11,501 total
includes taxes & fees
Sep 27 - Sep 28
Teschemakers Resort
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.
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
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
Peaceful cottage in private garden setting.
Property grounds

Peaceful cottage in private garden setting.

10.0 out of 10, Exceptional, (3)
"Very clean , warm and quiet . "
The price is ￥17,123
￥22,459 total
includes taxes & fees
Sep 30 - Oct 1
Peaceful cottage in private garden setting.
Kakanui Coastal Retreat
Smart TV, fireplace

Kakanui Coastal Retreat

The price is ￥21,620
￥41,207 total
includes taxes & fees
Sep 26 - Sep 27
Kakanui Coastal Retreat
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"
The price is ￥15,134
￥26,636 total
includes taxes & fees
Sep 28 - Sep 29
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, (67)
"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 ￥15,134
￥20,172 total
includes taxes & fees
Oct 11 - Oct 12
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"
The price is ￥27,673
￥42,936 total
includes taxes & fees
Sep 28 - Sep 29
Kakanui Cube
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!!!"
The price is ￥10,377
￥15,894 total
includes taxes & fees
Sep 26 - Sep 27
Oamaru travel mates house
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.
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."
The price is ￥22,406
￥26,710 total
includes taxes & fees
Sep 28 - Sep 29
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...
The price is ￥14,905
￥20,070 total
includes taxes & fees
Oct 1 - Oct 2
Forest Hill Farm by Tiny Away
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"
The price is ￥22,484
￥22,484 total
includes taxes & fees
Sep 28 - Sep 29
Historic School in rural Oamaru with farm animals and outdoor baths
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."
The price is ￥21,620
￥27,630 total
includes taxes & fees
Oct 10 - Oct 11
Little Sweetie in the Heart of Old Oamaru
Cozy 2 Bedrooms Lavender Garden House at Oamaru, sweet as home!
Property grounds

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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Top Windsor Hotel Reviews

Colonial Lodge Motel

Colonial Lodge Motel

10/10 Excellent
"Units are nicely decorated, beds comfortable and everything provided for an enjoyable stay. Traffic noise is very noticeable at night so request a rear unit fartherest from the road. "
Glenn 1-night trip
Posted 6 days ago
Colonial Lodge Motel

Find out more about Windsor

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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?

Watch the weather roll in along the coast with sea views from every room. : This vacation home rental near Windsor is located on the beach and has a fireplace, a patio, and a barbecue grill 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. You can relax into your vacation 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 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.