Windsor Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Windsor

Teschemakers Resort

2.5 star property
9.4 out of 10, Exceptional, (3)
"I had no idea when I booked this that it was a historic property. It was like staying in a National Landmark building...big, old world craftsmanship, richly appointed. Very pleasantly surprised."
The price is AU$173
includes taxes & fees
23 Feb - 24 Feb
Teschemakers Resort

The Sea View BnB

9.0 out of 10, Wonderful, (6)
"Lovely house but some light bulbs not working one only teaspoon no instructions for stove lack of wardrobes TV similar plus lack of mirrors "
The price is AU$290
includes taxes & fees
3 Mar - 4 Mar
The Sea View BnB

Beautiful ocean view from this lovely holiday home

9.6 out of 10, Exceptional, (243)
"Kakanui is a beautiful small town with lots of activities to offer. Kim is easy to communicate with. The place is clean and has what you need to eat at home and sleep well. Comfy beds, and warm blankets. The sunroom is lovely with a fantastic view of Kakanui beach and the rivermouth. Nice garden to walk around the property. Kind neighbors too. We will stay there again"
Beautiful ocean view from this lovely holiday home

The Sun set Cottage 5min from Oamaru or Kakanui

10.0 out of 10, Exceptional, (41)
"We just loved the property. Well set out with lovely countryside views. Fantastic sun rises and sunsets too and only a short drive to Oamaru."
The Sun set Cottage 5min from Oamaru or Kakanui

Stone Cottage in Central Oamaru (No Extra Cleaning Fee)

8.8 out of 10, Excellent, (37)
"We had a great one night stay at Orla's Cottage in Oamaru. Just a little further from the town centre than we would've wanted to walk, but the home was comfortable and clean and good for our little family. Would recommend this place to others. "
The price is AU$236
includes taxes & fees
2 Mar - 3 Mar
Stone Cottage in Central Oamaru (No Extra Cleaning Fee)

Comfortable family home with beautiful wild gardens to enjoy.

The price is AU$270
includes taxes & fees
3 Mar - 4 Mar
Comfortable family home with beautiful wild gardens to enjoy.

Oamaru travel mates house

4.0 out of 10, (1)
"From the adverts we had seen on Bokkabach and seeing that the payment had gone to Bookabach and also seeing in their listing the details started with entire house we expected to have the house to ourselves and not sharing it. I would not recommend this property to anyone else."
The price is AU$168
includes taxes & fees
23 Feb - 24 Feb
Oamaru travel mates house

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

9.2 out of 10, Wonderful, (71)
"Awesome place, highly recommend!"
The price is AU$389
includes taxes & fees
24 Feb - 25 Feb
Watch the weather roll in along the coast with sea views from every room.

Breathtaking sea view house

9.8 out of 10, Exceptional, (57)
"Lovely stay. Loved all the personal touches. Thanks heaps."
The price is AU$416
includes taxes & fees
25 Feb - 26 Feb
Breathtaking sea view house

Highlands on Homestead -Tranquil rural property only minutes from town

10.0 out of 10, Exceptional, (63)
"Beautiful stay in a quiet, peaceful location. Place was immaculate and the farm animals an absolute delight. The night skies are beautiful as no light pollution. Thank you for a wonderful stay Jenny and Andrew. "
The price is AU$214
includes taxes & fees
20 Mar - 21 Mar
Highlands on Homestead -Tranquil rural property only minutes from town

Herbert Forest Retreat 15 min from Oamaru, H/tub and MTB tracks

9.4 out of 10, Exceptional, (3)
"Great stay. Warm,clean house with everything you need for a get away."
Herbert Forest Retreat 15 min from Oamaru, H/tub and MTB tracks

Forest Hill Farm by Tiny Away

6.0 out of 10, (1)
"The tiny home was perfectly fine, amenities were good, and the bunny watching from the window was very cute. However the email that arrived just prior to check-in that advised the use of earplugs to block the sound of traffic and trains…well it was good advice, but arrived a little too late. The perpetual falling of objects from the trees overhead onto the metal roof of the house all together with the train rumbling through and trucks thundering by, lead to a less than decent sleep. For the...
The price is AU$209
includes taxes & fees
26 Feb - 27 Feb
Forest Hill Farm by Tiny Away

Cosy Dell Tiny House

10.0 out of 10, Exceptional, (2)
"Very peaceful, well appointed with excellent hosts."
The price is AU$200
includes taxes & fees
24 Feb - 25 Feb
Cosy Dell Tiny House

Little Sweetie in the Heart of Old Oamaru

10.0 out of 10, Exceptional, (39)
"We really enjoyed our stay at Little Sweetie. This is a very well appointed and comfortable place in an ideal location to enjoy the town. "
The price is AU$291
includes taxes & fees
3 Mar - 4 Mar
Little Sweetie in the Heart of Old Oamaru

180 degrees sea view

9.4 out of 10, Exceptional, (6)
"Clean, tidy, with nice king size beds"
The price is AU$345
includes taxes & fees
2 Mar - 3 Mar
180 degrees sea view

Oamaru Accommodation - Cozy On Till

8.8 out of 10, Excellent, (14)
"A lovely well appointed property, very comfy bed, perfect for our wee companion dog, well fenced. A well appointed home. Close to town and the public garden, just a lovely quiet spot to have a break away. We loved it. Thanks Shirley and Ian."
Oamaru Accommodation - Cozy On Till

Sea Breeze Apartment - Kakanui

9.2 out of 10, Wonderful, (5)
The price is AU$330
includes taxes & fees
24 Feb - 25 Feb
Sea Breeze Apartment - Kakanui

Cosy seaside villa with a pool table!

8.0 out of 10, Very good, (1)
The price is AU$449
includes taxes & fees
28 Feb - 1 Mar
Cosy seaside villa with a pool table!

Historic Cottage in rural Oamaru with farm animals and outdoor baths

9.8 out of 10, Exceptional, (20)
"Grouse as! Awesome hidden gem if you're wanting a quiet getaway far from the crowded tourist hotspots. "
The price is AU$216
includes taxes & fees
25 Feb - 26 Feb
Historic Cottage in rural Oamaru with farm animals and outdoor baths

Cosy bach with Kakanui mountain and sea views.

Cosy bach with Kakanui mountain and sea views.
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.
Don't see what you're looking for?
See all available properties in Windsor
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Windsor you may be interested in

Brydone Hotel Oamaru

3.5 star property
8.4 out of 10, Very good, (499)
"Thank you for the receptionist service as we arrived after 10pm"
The price is AU$158
includes taxes & fees
4 Mar - 5 Mar
Brydone Hotel Oamaru

Ascot Oamaru Motel

3.0 star property
7.6 out of 10, Good, (419)
"Our stay was excellent, staff friendly just concerned bathroom floor slippery when wet "
The price is AU$181
includes taxes & fees
1 Mar - 2 Mar
Ascot Oamaru Motel

Heritage Court Lodge

4.0 star property
8.4 out of 10, Very good, (340)
"Could not get the tv to work"
The price is AU$154
includes taxes & fees
27 Feb - 28 Feb
Heritage Court Lodge
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.

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 North Otago Museum 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.