Windsor Holiday Rentals from AU$153: Search Short-Term Rentals

Q: 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.

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Our top choices for Windsor holiday rentals

A large, multi-story building with a symmetrical facade, multiple windows, and a central entrance.

1. Teschemakers Resort

Teschemakers

Jawid

includes taxes & fees

6 Dec - 7 Dec

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

2. Historic School in rural Oamaru with farm animals and outdoor baths

Oamaru

Sally E.

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with white cabinetry, a stainless steel range hood, a built-in oven, a dishwasher, and a window providing natural light.

3. Little Sweetie in the Heart of Old Oamaru

South Hill

Trudy M.

includes taxes & fees

22 Nov - 23 Nov

A room with a large window offering a view of a coastal landscape, a small table with a decorative item, and a clear sky.

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

Kakanui

includes taxes & fees

11 Nov - 12 Nov

5. Bluegum Lodge Farmstay

Deborah

includes taxes & fees

5 Dec - 6 Dec

6. Romantic B&B Cottage Getaway on a Farm in the Countryside near Oamaru, South Island

Oamaru

includes taxes & fees

8 Nov - 9 Nov

A beach with a wide sandy shore, gentle waves, and a clear sky.

7. Classic Kiwi Bach: Kakanui Beach Escape.

Kakanui

Rod & Sarah B.

includes taxes & fees

8 Nov - 9 Nov

A modern cabin with large windows, a stone foundation, and a view of the surrounding forest.

8. Cosy Dell Tiny House

Herbert

David

includes taxes & fees

9 Nov - 10 Nov

A bench by a calm harbor with boats and a hillside in the background.

9. Oamaru Accommodation - Cozy On Till

South Hill

Meghan F.

includes taxes & fees

23 Nov - 24 Nov

A balcony with a view of a coastal town, wooden deck, and a clear sky.

10. 180 degrees sea view

Oamaru North

Hamish V.

includes taxes & fees

8 Nov - 9 Nov

11. Luxury Dome with Hot Tub (Kārearea)

Danseys Pass

includes taxes & fees

22 Nov - 23 Nov

A modern kitchen with a central island, built-in appliances, and a dining area with a table and chairs.

12. 3BR stylish home base for exploring town, comfort meets prime location

Oamaru

includes taxes & fees

9 Nov - 10 Nov

A modern interior with a wooden dining table, a white sofa, and a glass door leading to a balcony.

13. The Bach Retreat Kakanui

Kakanui

Lauren K.

includes taxes & fees

8 Nov - 9 Nov

A dining area with a table and chairs, a window with a view of the ocean, and curtains.

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

Kakanui

Mikaela W.

includes taxes & fees

4 Dec - 5 Dec

A modern kitchen with a large window, white cabinetry, and a stainless steel sink.

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

South Hill

M C.

includes taxes & fees

10 Nov - 11 Nov

A balcony with a view of the sea and buildings, a chair, and a white rug.

16. Breathtaking sea view house

Oamaru North

Sharon W.

includes taxes & fees

8 Nov - 9 Nov

A wooden deck with steps leading to a seating area, surrounded by lush greenery and a view of a hill.

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

South Hill

includes taxes & fees

6 Dec - 7 Dec

A dining area with a table set for two, a sofa, and a view of the ocean.

18. Kakanui Coast Retreat

Kakanui

includes taxes & fees

22 Nov - 23 Nov

A cozy room with a sofa, a fireplace, and a view of a mountainous landscape through a geometric window.

19. Mountain View Dome & Private Hot Tub (Piwakawaka)

Danseys Pass

includes taxes & fees

16 Nov - 17 Nov

20. Family-Fun Villa, Moonrise & Sunrise! Kids' Slide Bed! Ocean & Town Views 5-Beds

Oamaru North

includes taxes & fees

10 Nov - 11 Nov

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Find holiday rentals that suit your style

Top Windsor Hotel Reviews

A black car parked in front of a building with a white exterior and a black roof.

Oamaru Motor Lodge

Oamaru North

10/10 Excellent

Heathet

A spacious lobby with a wooden floor, leather sofas, a red chair, and multiple hanging lights.

Poshtel

Oamaru

10/10 Excellent

Anonymous traveller

A multi-story hotel with a brick driveway and a landscaped garden.

The Mews Oamaru

Oamaru

10/10 Excellent

Anonymous traveller

A bed with a grey quilt and red pillows, a red and white striped throw, and a white headboard.

Colonial Lodge Motel

Oamaru North

10/10 Excellent

Anonymous traveller

Teschemakers Resort

Teschemakers

10/10 Excellent

Melissa

A commercial laundry area with two stacked washers and a dryer, a safety warning sign, and a potted plant.

ASURE Ambassador Motor Lodge

Oamaru North

10/10 Excellent

Shannon

A well-maintained garden with a flowering tree, a stone border, and a lawn.

289 Midway Motel

Oamaru

10/10 Excellent

Ian

A restaurant with wooden beams, tables, chairs, and menu boards.

Ascot Oamaru Motel

Oamaru North

10/10 Excellent

Mark

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as AU$153 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 Harbour. 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.

Windsor Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor holiday rentals

1. Teschemakers Resort

2. Historic School in rural Oamaru with farm animals and outdoor baths

3. Little Sweetie in the Heart of Old Oamaru

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

5. Bluegum Lodge Farmstay

6. Romantic B&B Cottage Getaway on a Farm in the Countryside near Oamaru, South Island

7. Classic Kiwi Bach: Kakanui Beach Escape.

8. Cosy Dell Tiny House

9. Oamaru Accommodation - Cozy On Till

10. 180 degrees sea view

11. Luxury Dome with Hot Tub (Kārearea)

12. 3BR stylish home base for exploring town, comfort meets prime location

13. The Bach Retreat Kakanui

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

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

16. Breathtaking sea view house

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

18. Kakanui Coast Retreat

19. Mountain View Dome & Private Hot Tub (Piwakawaka)

20. Family-Fun Villa, Moonrise & Sunrise! Kids' Slide Bed! Ocean & Town Views 5-Beds

Find holiday rentals that suit your style

Top Windsor Hotel Reviews

Oamaru Motor Lodge

10/10 Excellent

Find out more about Windsor

Windsor holiday rentals: An excellent choice for every season

How to find incredible deals on Windsor rentals

Frequently Asked Questions

Can I find holiday rentals in Windsor?

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

What’s there to see and do in Windsor?

What are holiday rentals like in Windsor?