Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

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 CA $187
CA $215 total
includes taxes & fees
Jun 6 - Jun 7
Teschemakers Resort

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, (85 reviews)
"Great location…loved the sun porch"
United States
Steve M.
The price is CA $173
CA $327 total
includes taxes & fees
Jun 2 - Jun 3
Watch the weather roll in along the coast with sea views from every room.

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 CA $210
CA $210 total
includes taxes & fees
May 22 - May 23
Historic School in rural Oamaru with farm animals and outdoor baths

Little Sweetie in the Heart of Old Oamaru

Little Sweetie in the Heart of Old Oamaru
South Hill
10.0 out of 10, Exceptional, (55 reviews)
"Beautiful property "
United Kingdom
Sara
The price is CA $201
CA $257 total
includes taxes & fees
Jun 1 - Jun 2
Little Sweetie in the Heart of Old Oamaru

Kakanui Cube

Kakanui Cube
Kakanui
9.8 out of 10, Exceptional, (36 reviews)
"Great place , had a great time tks"
Australia
Michael
The price is CA $217
CA $330 total
includes taxes & fees
Jun 1 - Jun 2
Kakanui Cube

The Bach Retreat Kakanui

The Bach Retreat Kakanui
Kakanui
9.8 out of 10, Exceptional, (74 reviews)
"It was fabulous - we loved everything about the place - just super."
New Zealand
Jen S.
The price is CA $209
CA $361 total
includes taxes & fees
May 25 - May 26
The Bach Retreat Kakanui

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 CA $215
CA $245 total
includes taxes & fees
May 22 - May 23
Romantic B&B Cottage Getaway on a Farm in the Countryside near Oamaru, South Island

Cosy Dell by Tiny Away

Cosy Dell by Tiny Away
Herbert
10.0 out of 10, Exceptional, (4 reviews)
"Very peaceful, well appointed with excellent hosts."
Australia
David
The price is CA $129
CA $169 total
includes taxes & fees
Jun 3 - Jun 4
Cosy Dell by Tiny Away

Kakanui Coastal Living with Panoramic Ocean Views

Kakanui Coastal Living with Panoramic Ocean Views
Kakanui
10.0 out of 10, Exceptional, (5 reviews)
"Amenities, consumables, location, settingEverything fabulous If coming to this part again would want to stay thereCant praise it highly enough "
United Kingdom
Geoffrey H.
The price is CA $258
CA $488 total
includes taxes & fees
May 22 - May 23
Kakanui Coastal Living with Panoramic Ocean Views

Breathtaking sea view house

Breathtaking sea view house
Oamaru North
9.8 out of 10, Exceptional, (71 reviews)
"The house was lovely, clean and spacious. Our host left us a bottle of wine to enjoy, which we appreciated. The view was breathtaking as we were at the top of the road. Kitchen was fully equipped with lots of place to work in."
Australia
Carolyn
The price is CA $254
CA $450 total
includes taxes & fees
May 26 - May 27
Breathtaking sea view house

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 CA $193
CA $315 total
includes taxes & fees
Jun 1 - Jun 2
Sea Breeze Apartment - Kakanui

Tyne above Town - Convenient. Comfortable. Clean.

Tyne above Town - Convenient. Comfortable. Clean.
South Hill
The price is CA $210
CA $258 total
includes taxes & fees
May 25 - May 26
Tyne above Town - Convenient. Comfortable. Clean.

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 CA $159
CA $308 total
includes taxes & fees
May 24 - May 25
180 degrees sea view

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 CA $237
CA $297 total
includes taxes & fees
Jun 1 - Jun 2
Top of Tyne - Peace, Comfort & Local Connection

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 CA $830
CA $1,175 total
includes taxes & fees
May 22 - May 23
Family-Fun Villa, Moonrise & Sunrise! Kids' Slide Bed! Ocean & Town Views 5-Beds
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

Find out more about Windsor

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, there are vacation rentals near well known sights in Windsor, or you can choose a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Windsor has to offer?

Watch the weather roll in along the coast with sea views from every room. : This vacation home rental near Windsor is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You can relax into your vacation 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 larger area, you’ll find Janet Frame House and Alps 2 Ocean Cycle Trail.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can reserve for several days or more in Windsor. Vacation 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 sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering.