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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Windsor holiday rentals

A red house with a porch, a small deck, and a lawn.

1. 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, (26 reviews)
"Awesome night away ar The Little Red School House, so peaceful and relaxing with the outdoor baths"
United States
Sally E.
The price is HK$1,198
HK$1,198 total
includes taxes & fees
11 Sept - 12 Sept
Historic School in rural Oamaru with farm animals and outdoor baths

2. 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$1,366
HK$1,366 total
includes taxes & fees
13 Sept - 14 Sept
Romantic B&B Cottage Getaway on a Farm in the Countryside near Oamaru, South Island
A large, multi-story building with a symmetrical facade, multiple windows, and a central entrance.

3. Teschemakers Resort

Teschemakers Resort
3.0 star property
Teschemakers
9.4 out of 10, Exceptional, (11 reviews)
"Very nice and quiet!"
Australia
Jawid
The price is HK$1,069
HK$1,229 total
includes taxes & fees
22 Sept - 23 Sept
Teschemakers Resort
A modern kitchen with white cabinetry, a stainless steel range hood, a built-in oven, a dishwasher, and a window providing natural light.

4. Little Sweetie in the Heart of Old Oamaru

Little Sweetie in the Heart of Old Oamaru
South Hill
10.0 out of 10, Exceptional, (60 reviews)
"Very convenient location to centre of town, good beds."
Australia
Simon
The price is HK$1,152
HK$1,491 total
includes taxes & fees
9 Sept - 10 Sept
Little Sweetie in the Heart of Old Oamaru
A hotel room with a bed, a blue sofa, a desk with a chair, a large window with a view of the city, and a painting on the wall.

5. Joy 40 Apartments Oamaru

Joy 40 Apartments Oamaru
4.0 star property
Oamaru
The price is HK$966
HK$1,111 total
includes taxes & fees
1 Oct - 2 Oct
Joy 40 Apartments Oamaru
A bench by a calm harbor with boats and a hillside in the background.

6. Oamaru Accommodation - Cozy On Till

Oamaru Accommodation - Cozy On Till
South Hill
8.8 out of 10, Excellent, (15 reviews)
"This is the cutest little house in exactly the part of town you want to be in. Perfect for my two-night stay- and they had great recommendations that made the stay even better"
United States
Meghan F.
The price is HK$691
HK$1,208 total
includes taxes & fees
10 Sept - 11 Sept
Oamaru Accommodation - Cozy On Till
A balcony with a view of the sea and buildings, a chair, and a white rug.

7. Breathtaking sea view house

Breathtaking sea view house
Oamaru North
9.8 out of 10, Exceptional, (72 reviews)
"Warm and lovely place to stay. Sea view is a plus. Will defi back again "
New Zealand
Kar E.
The price is HK$1,613
HK$2,998 total
includes taxes & fees
9 Sept - 10 Sept
Breathtaking sea view house
A balcony with a view of a coastal town, wooden deck, and a clear sky.

8. 180 degrees sea view

180 degrees sea view
Oamaru North
9.8 out of 10, Exceptional, (11 reviews)
"Great central location, warm house and comfortable beds "
New Zealand
Hamish V.
The price is HK$1,037
HK$2,117 total
includes taxes & fees
9 Sept - 10 Sept
180 degrees sea view
A modern interior with a wooden dining table, a white sofa, and a glass door leading to a balcony.

9. The Bach Retreat Kakanui

The Bach Retreat Kakanui
Kakanui
9.8 out of 10, Exceptional, (76 reviews)
"Beautiful property a lovely setting."
United States
Lauren K.
The price is HK$1,198
HK$2,003 total
includes taxes & fees
10 Sept - 11 Sept
The Bach Retreat Kakanui
A modern kitchen with a large window, white cabinetry, and a stainless steel sink.

10. Top of Tyne - Peace, Comfort & Local Connection

Top of Tyne - Peace, Comfort & Local Connection
South Hill
10.0 out of 10, Exceptional, (3 reviews)
"Very neat and clean. Modernized and upgraded facilities and the host put the heat pump on before we arrived so we were warm when we got there!"
United States
M C.
The price is HK$1,751
HK$1,751 total
includes taxes & fees
9 Sept - 10 Sept
Top of Tyne - Peace, Comfort & Local Connection
A modern cabin with large windows, a stone foundation, and a view of the surrounding forest.

11. 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$731
HK$960 total
includes taxes & fees
20 Sept - 21 Sept
Cosy Dell Tiny House
A wooden deck with steps leading to a seating area, surrounded by lush greenery and a view of a hill.

12. Tyne above Town - Convenient. Comfortable. Clean.

Tyne above Town - Convenient. Comfortable. Clean.
South Hill
The price is HK$1,544
HK$1,820 total
includes taxes & fees
9 Sept - 10 Sept
Tyne above Town - Convenient. Comfortable. Clean.

13. Ocean View on Semple, Your Coastal Haven Retreat. Relax in seaside charm!

Ocean View on Semple, Your Coastal Haven Retreat. Relax in seaside charm!
Kakanui
The price is HK$1,383
HK$2,383 total
includes taxes & fees
19 Sept - 20 Sept
Ocean View on Semple, Your Coastal Haven Retreat. Relax in seaside charm!

14. 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$4,770
HK$6,675 total
includes taxes & fees
9 Sept - 10 Sept
Family-Fun Villa, Moonrise & Sunrise! Kids' Slide Bed! Ocean & Town Views 5-Beds
A kitchen with a microwave, toaster, and a knife block.

15. Seaview Hill Retreat - You Will Love the View & Enjoy Your Time Here

Seaview Hill Retreat - You Will Love the View & Enjoy Your Time Here
Oamaru
The price is HK$2,854
HK$3,641 total
includes taxes & fees
13 Sept - 14 Sept
Seaview Hill Retreat - You Will Love the View & Enjoy Your Time Here
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
"Quirky featured room very comfortable bed excellent bathroom great TV channels top breakfast."
William 1-night trip
Posted 18 hours ago
Poshtel

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 Gardens. In the wider area, you’ll find Steampunk HQ and Oamaru Victorian Heritage Precinct.

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.