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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Windsor holiday rentals

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, (26 reviews)
"This place is amazing we loved our stay and didn’t want to leave"
United Kingdom
Anonymous traveller
The price is HK$1,185
HK$1,185 total
includes taxes & fees
27 Jul - 28 Jul
Historic School in rural Oamaru with farm animals and outdoor baths
Exterior

Joy 40 Apartments Oamaru

Joy 40 Apartments Oamaru
2.0 star property
Oamaru
Joy 40 Apartments Oamaru
Exterior

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$1,303
HK$1,303 total
includes taxes & fees
26 Jul - 27 Jul
Romantic B&B Cottage Getaway on a Farm in the Countryside near Oamaru, South Island
Exterior

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$1,057
HK$1,216 total
includes taxes & fees
9 Aug - 10 Aug
Teschemakers Resort
Interior

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$1,003
HK$1,887 total
includes taxes & fees
12 Aug - 13 Aug
180 degrees sea view
Interior

Breathtaking sea view house

Breathtaking sea view house
Oamaru North
9.8 out of 10, Exceptional, (71 reviews)
"Warm and lovely place to stay. Sea view is a plus. Will defi back again "
New Zealand
Kar E.
The price is HK$1,139
HK$2,181 total
includes taxes & fees
3 Aug - 4 Aug
Breathtaking sea view house
Coffee/tea maker, fridge, microwave, oven

Little Sweetie in the Heart of Old Oamaru

Little Sweetie in the Heart of Old Oamaru
South Hill
10.0 out of 10, Exceptional, (56 reviews)
"A great stay, thanks"
New Zealand
Ann E.
The price is HK$1,139
HK$1,474 total
includes taxes & fees
4 Aug - 5 Aug
Little Sweetie in the Heart of Old Oamaru
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$620
HK$847 total
includes taxes & fees
6 Aug - 7 Aug
Cosy Dell Tiny House
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, (87 reviews)
"Great location…loved the sun porch"
United States
Steve M.
The price is HK$1,124
HK$2,044 total
includes taxes & fees
6 Aug - 7 Aug
Watch the weather roll in along the coast with sea views from every room.
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$4,717
HK$6,623 total
includes taxes & fees
24 Jul - 25 Jul
Family-Fun Villa, Moonrise & Sunrise! Kids' Slide Bed! Ocean & Town Views 5-Beds
Outdoor dining

The Bach Retreat Kakanui

The Bach Retreat Kakanui
Kakanui
9.8 out of 10, Exceptional, (76 reviews)
"Always have a wonderful experience when I stay at this retreat."
New Zealand
Debbie A.
The price is HK$1,185
HK$2,062 total
includes taxes & fees
6 Aug - 7 Aug
The Bach Retreat Kakanui
Smart TV, fireplace

Kakanui Coastal Living with Panoramic Ocean Views

Kakanui Coastal Living with Panoramic Ocean Views
Kakanui
10.0 out of 10, Exceptional, (5 reviews)
"House was fantastic, great views and space for our family. Amenities were great, all we could need."
New Zealand
Kellee M.
The price is HK$1,179
HK$2,397 total
includes taxes & fees
24 Jul - 25 Jul
Kakanui Coastal Living with Panoramic Ocean Views
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, (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$1,436
HK$1,800 total
includes taxes & fees
7 Aug - 8 Aug
Top of Tyne - Peace, Comfort & Local Connection
Terrace/patio

Tyne above Town - Convenient. Comfortable. Clean.

Tyne above Town - Convenient. Comfortable. Clean.
South Hill
The price is HK$1,303
HK$1,577 total
includes taxes & fees
12 Aug - 13 Aug
Tyne above Town - Convenient. Comfortable. Clean.
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
"Friendly staff, and a comfortable bed in a clean room. Liked having sky tv!!!!"
Denise 1-night trip
Posted 14 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
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  • 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?

The Bach Retreat Kakanui: This holiday home rental outside of Windsor is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 Janet Frame House and Steampunk HQ.

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.