Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Windsor vacation rentals

Exterior

Teschemakers Resort

Teschemakers Resort
3.0 star property
Teschemakers
9.4 out of 10, Exceptional, (8 reviews)
"Very nice and quiet!"
Australia
Jawid
The price is ￥20,761
￥23,875 total
includes taxes & fees
Feb 27 - Feb 28
Teschemakers Resort
Exterior

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, (23 reviews)
"Lovely hosts and fabulous house"
New Zealand
Lisa N.
The price is ￥23,962
￥23,962 total
includes taxes & fees
Mar 1 - Mar 2
Historic School in rural Oamaru with farm animals and outdoor baths
Interior

Kakanui Cube

Kakanui Cube
Kakanui
9.8 out of 10, Exceptional, (33 reviews)
"Great place , had a great time tks"
Australia
Michael
The price is ￥29,492
￥43,547 total
includes taxes & fees
Mar 1 - Mar 2
Kakanui Cube
Dining

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

Watch the weather roll in along the coast with sea views from every room.
Kakanui
9.2 out of 10, Wonderful, (82 reviews)
"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."
New Zealand
Jo-Anne S.
The price is ￥19,907
￥36,810 total
includes taxes & fees
Mar 6 - Mar 7
Watch the weather roll in along the coast with sea views from every room.
Outdoor dining

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 ￥98,706
￥127,522 total
includes taxes & fees
Mar 2 - Mar 3
Exquisite Luxury Property with Stunning Views
Fridge, microwave, oven, stovetop

Little Sweetie in the Heart of Old Oamaru

Little Sweetie in the Heart of Old Oamaru
South Hill
10.0 out of 10, Exceptional, (50 reviews)
"Lovely sensitively converted early home, lots of conveniences, comfortable and easy walking to town. "
Australia
Anita
The price is ￥23,041
￥29,446 total
includes taxes & fees
Feb 28 - Mar 1
Little Sweetie in the Heart of Old Oamaru
Beach

Sea Breeze Apartment - Kakanui

Sea Breeze Apartment - Kakanui
Kakanui
9.6 out of 10, Exceptional, (8 reviews)
"Gorgeous property close to the sea! "
New Zealand
Aoife W.
The price is ￥22,119
￥35,553 total
includes taxes & fees
Feb 27 - Feb 28
Sea Breeze Apartment - Kakanui
Exterior

Cosy Dell by Tiny Away

Cosy Dell by Tiny Away
Herbert
10.0 out of 10, Exceptional, (4 reviews)
"Very peaceful, well appointed with excellent hosts."
Australia
David
The price is ￥13,550
￥18,161 total
includes taxes & fees
Mar 1 - Mar 2
Cosy Dell by Tiny Away
Fridge, microwave, oven, stovetop

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 ￥29,492
￥36,865 total
includes taxes & fees
Mar 10 - Mar 11
Top of Tyne - Peace, Comfort & Local Connection
Interior

Breathtaking sea view house

Breathtaking sea view house
Oamaru North
9.8 out of 10, Exceptional, (68 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 ￥27,649
￥48,846 total
includes taxes & fees
Mar 15 - Mar 16
Breathtaking sea view house
Interior

180 degrees sea view

180 degrees sea view
Oamaru North
9.6 out of 10, Exceptional, (8 reviews)
"A nice house with all the necessities"
United States
Gen W.
The price is ￥18,248
￥32,966 total
includes taxes & fees
Mar 1 - Mar 2
180 degrees sea view
Dining

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 ￥95,389
￥135,135 total
includes taxes & fees
Mar 4 - Mar 5
Family-Fun Villa, Moonrise & Sunrise! Kids' Slide Bed! Ocean & Town Views 5-Beds
Exterior detail

Comfortable family home with beautiful wild gardens to enjoy.

Comfortable family home with beautiful wild gardens to enjoy.
South Hill
9.6 out of 10, Exceptional, (5 reviews)
"Internet reception very poor/no instruction for tv combined with poor internet reception we were unable to view any programs "
Australia
Wendy
The price is ￥14,746
￥27,418 total
includes taxes & fees
Mar 23 - Mar 24
Comfortable family home with beautiful wild gardens to enjoy.
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

Beautiful ocean view from this lovely holiday home

Beautiful ocean view from this lovely holiday home

10/10 Excellent
"Great outlook and location. House perfect for a short stay"
Grant A. 2-night trip
Posted 3 days ago
Beautiful ocean view from this lovely holiday home

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?

Beautiful ocean view from this lovely holiday home: This vacation home near 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 larger area, you’ll find Janet Frame House and North Otago Museum.

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.