Windsor Holiday Rentals

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Holiday Rentals in Windsor

Teschemakers Resort

2.5 star property
The price is S$196
includes taxes & fees
20 Dec - 21 Dec
Teschemakers Resort

Oamaru Holiday Homes 8 Oxford Street

3.5 star property
Oamaru Holiday Homes 8 Oxford Street

Harold House

4.5 star property
9.6 out of 10, Exceptional, (4)
"Spacious home close to everything, the outside of the property looks so plain but once you walk inside it is beautifully renovated. Loved it."
Harold House

Oamaru Holiday Homes 92 Aln Street

4.0 star property
9.6 out of 10, Exceptional, (12)
"Loved the view.Would stay again for sure. Not sure you are aware the side cupboards in the bathroom are broken,just looking at them you would think they are ok, but as soon as you open the whole lot collapses. And just one other comment your cleaners need to lift the bottom of shower drain, it was disgusting as it was filled with black long hair and a little blocked. We did clean it for you. In saying this we would definitely be back."
Oamaru Holiday Homes 92 Aln Street

180 Degrees sea view house

3.0 star property
180 Degrees sea view house

Oamaru Holiday Homes 28 Ure Street

3.5 star property
Oamaru Holiday Homes 28 Ure Street

Sunny & Quiet in Blyth with unlimited fibre WIFI

3.0 star property
10.0 out of 10, Exceptional, (2)
"It was wonderful to have a whole bungalow to ourselves, in such a quiet area, yet only a couple of minutes drive into fascinating Oamaru (where there's plenty of free parking). The beds were very comfortable, a lovely spacious lounge, with 2 large sofas, and it was good to be able to cook our own meals in a proper kitchen, rather than having to eat out each night. In short, it felt like home! Fred couldn't have been more helpful and kept in prompt contact for all our needs. "
Sunny & Quiet in Blyth with unlimited fibre WIFI

Oamaru Holiday Homes Largo House

3.5 star property
10.0 out of 10, Exceptional, (10)
"Very well suited for our group and had everything we needed."
Oamaru Holiday Homes Largo House

Penguin Retreat

2.5 star property
Penguin Retreat

Glen Warren View

3.5 star property
10.0 out of 10, Exceptional, (4)
"Wonderful view and lots of space. Need to park on the side of the road and walk down a short flight of stairs to get to the entrance because the driveway is quite steep. Great location-close to town and penguin observation area. Would stay here again for sure"
Glen Warren View
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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Other types of properties in Windsor you may be interested in

Oamaru Motor Lodge

4.0 star property
9.6 out of 10, Exceptional, (640)
"Very nice modern apartment good location too for visiting the penguins in the evening"
The price is S$123
includes taxes & fees
7 Dec - 8 Dec
Oamaru Motor Lodge

Brydone Hotel Oamaru

3.5 star property
8.4 out of 10, Very good, (472)
"Just a good place to stay in the middle of town. Nice friendly staff."
The price is S$124
includes taxes & fees
26 Nov - 27 Nov
Brydone Hotel Oamaru

Poshtel

5.0 star property
9.6 out of 10, Exceptional, (250)
"Very well-decorated room in a renovated historic building on a busy road. The front desk person was very friendly and helpful. The room was small but cozy. The parking was a block away, which wasn't a problem, but there wasn't any place to drop off your luggage while you checked in. The continental breakfast had high quality food, but not many choices. I felt like overall it was a good place for one night, but not an extended stay. "
The price is S$147
includes taxes & fees
8 Dec - 9 Dec
Poshtel
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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’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 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.