Windsor Holiday Rentals

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Windsor holiday rentals

Exterior

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 HK$738
HK$969 total
includes taxes & fees
28 Apr - 29 Apr
Cosy Dell Tiny House
Exterior

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 HK$1,071
HK$1,231 total
includes taxes & fees
11 May - 12 May
Teschemakers Resort
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, (84 reviews)
"Great location…loved the sun porch"
United States
Steve M.
The price is HK$997
HK$1,885 total
includes taxes & fees
24 Apr - 25 Apr
Watch the weather roll in along the coast with sea views from every room.
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, (24 reviews)
"Lovely hosts and fabulous house"
New Zealand
Lisa N.
The price is HK$1,200
HK$1,200 total
includes taxes & fees
25 Apr - 26 Apr
Historic School in rural Oamaru with farm animals and outdoor baths
Beach

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 HK$1,108
HK$1,822 total
includes taxes & fees
24 Apr - 25 Apr
Sea Breeze Apartment - Kakanui
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, (54 reviews)
"Beautiful property "
United Kingdom
Sara
The price is HK$1,154
HK$1,484 total
includes taxes & fees
10 May - 11 May
Little Sweetie in the Heart of Old Oamaru
Interior

Kakanui Cube

Kakanui Cube
Kakanui
9.8 out of 10, Exceptional, (35 reviews)
"Great place , had a great time tks"
Australia
Michael
The price is HK$1,246
HK$1,901 total
includes taxes & fees
24 Apr - 25 Apr
Kakanui Cube
Interior

180 degrees sea view

180 degrees sea view
Oamaru North
9.6 out of 10, Exceptional, (10 reviews)
"Great central location, warm house and comfortable beds "
New Zealand
Hamish V.
The price is HK$914
HK$1,780 total
includes taxes & fees
6 May - 7 May
180 degrees sea view
Property grounds

Romantic B&B Cottage Getaway on a Farm in the Countryside near Oamaru, South Island

Romantic B&B Cottage Getaway on a Farm in the Countryside near Oamaru, South Island
Oamaru
The price is HK$1,229
HK$1,405 total
includes taxes & fees
23 Apr - 24 Apr
Romantic B&B Cottage Getaway on a Farm in the Countryside near Oamaru, South Island
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, (2 reviews)
The price is HK$1,361
HK$1,685 total
includes taxes & fees
27 Apr - 28 Apr
Top of Tyne - Peace, Comfort & Local Connection
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 HK$4,777
HK$6,688 total
includes taxes & fees
26 Apr - 27 Apr
Family-Fun Villa, Moonrise & Sunrise! Kids' Slide Bed! Ocean & Town Views 5-Beds
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 HK$4,943
HK$6,317 total
includes taxes & fees
8 May - 9 May
Exquisite Luxury Property with Stunning Views
Interior

Breathtaking sea view house

Breathtaking sea view house
Oamaru North
9.8 out of 10, Exceptional, (70 reviews)
"Amazing stay. Accomation was fanatic. Clean, today and wonderful communication. Would stay again."
United States
Nicola C.
The price is HK$1,454
HK$2,516 total
includes taxes & fees
4 May - 5 May
Breathtaking sea view house
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

Brydone Hotel Oamaru

Brydone Hotel Oamaru

10/10 Excellent
"Breakfast"
Neil 1-night trip
Posted 3 hours ago
Brydone Hotel Oamaru

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 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 Steampunk HQ and Grainstore Gallery.

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.