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Windsor Vacation Rentals

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Windsor vacation rentals

Exterior

1. 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 traveler
$154 nightly
The price is $154
Sep 3 - Sep 4
Total with taxes and fees
Historic School in rural Oamaru with farm animals and outdoor baths
Exterior

2. 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
$169 nightly
The price is $169
Sep 3 - Sep 4
Total with taxes and fees
Romantic B&B Cottage Getaway on a Farm in the Countryside near Oamaru, South Island
Exterior

3. Teschemakers Resort

Teschemakers Resort
3.0 star property
Teschemakers
9.4 out of 10, Exceptional, (11 reviews)
"Very nice and quiet!"
Australia
Jawid
$137 nightly
The price is $158
Sep 13 - Sep 14
Total with taxes and fees
Teschemakers Resort
Coffee/tea maker, fridge, microwave, oven

4. Little Sweetie in the Heart of Old Oamaru

Little Sweetie in the Heart of Old Oamaru
South Hill
10.0 out of 10, Exceptional, (60 reviews)
"Very convenient location to centre of town, good beds."
Australia
Simon
$169 nightly
The price is $191
Sep 1 - Sep 2
Total with taxes and fees
Little Sweetie in the Heart of Old Oamaru
Interior

5. Breathtaking sea view house

Breathtaking sea view house
Oamaru North
9.8 out of 10, Exceptional, (72 reviews)
"Warm and lovely place to stay. Sea view is a plus. Will defi back again "
New Zealand
Kar E.
$344 nightly
The price is $390
Sep 4 - Sep 5
Total with taxes and fees
Breathtaking sea view house
Interior

6. 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.
$240 nightly
The price is $271
Sep 4 - Sep 5
Total with taxes and fees
180 degrees sea view
Beach

7. Oamaru Accommodation - Cozy On Till

Oamaru Accommodation - Cozy On Till
South Hill
8.8 out of 10, Excellent, (15 reviews)
"This is the cutest little house in exactly the part of town you want to be in. Perfect for my two-night stay- and they had great recommendations that made the stay even better"
United States
Meghan F.
$149 nightly
The price is $169
Sep 2 - Sep 3
Total with taxes and fees
Oamaru Accommodation - Cozy On Till
Outdoor dining

8. The Bach Retreat Kakanui

The Bach Retreat Kakanui
Kakanui
9.8 out of 10, Exceptional, (76 reviews)
"Beautiful property a lovely setting."
United States
Lauren K.
$236 nightly
The price is $267
Sep 1 - Sep 2
Total with taxes and fees
The Bach Retreat Kakanui
Exterior

9. 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
$110 nightly
The price is $110
Sep 1 - Sep 2
Total with taxes and fees
Cosy Dell by Tiny Away
Coffee/tea maker, fridge, microwave, oven

10. 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.
$225 nightly
The price is $225
Sep 8 - Sep 9
Total with taxes and fees
Top of Tyne - Peace, Comfort & Local Connection
Terrace/patio

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

Tyne above Town - Convenient. Comfortable. Clean.
South Hill
$234 nightly
The price is $234
Sep 1 - Sep 2
Total with taxes and fees
Tyne above Town - Convenient. Comfortable. Clean.
Interior

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

Ocean View on Semple, Your Coastal Haven Retreat. Relax in seaside charm!
Kakanui
$290 nightly
The price is $307
Sep 19 - Sep 20
Total with taxes and fees
Ocean View on Semple, Your Coastal Haven Retreat. Relax in seaside charm!
Property grounds

13. Seaview Hill Retreat - You Will Love the View & Enjoy Your Time Here

Seaview Hill Retreat - You Will Love the View & Enjoy Your Time Here
Oamaru
$418 nightly
The price is $473
Sep 1 - Sep 2
Total with taxes and fees
Seaview Hill Retreat - You Will Love the View & Enjoy Your Time Here
Dining

14. 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
$766 nightly
The price is $867
Sep 1 - Sep 2
Total with taxes and fees
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

Bella Vista Motel Oamaru

Bella Vista Motel Oamaru

8/10 Good
"Nice place to stay."
Peter 1-night trip
Posted 1 day ago
Bella Vista Motel Oamaru

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $110 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation 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 vacation.

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 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. : Located near Windsor, this vacation home rental 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 Gardens. In the larger area, you’ll find Steampunk HQ and Oamaru Victorian Heritage Precinct.

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.