Winslow Holiday Rentals

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Our top choices for Winslow holiday rentals

Cottage in Tower Hill

Harmony at Tower Hill
4.0 star property
9.4 out of 10, Exceptional, (92)
"This place is has very comfortable cabins within walking distance to the park where you can see koalas. It is also a short drive to Woornambool for services and restaurants "
Canada
Lynda
The price is NZ$247
includes taxes & fees
5 Jan - 6 Jan 2026
Harmony at Tower Hill
4.0 star property
9.0 out of 10, Wonderful, (111)
"Swim spa was amazing! Very nice cottage that is very well and thoughtfully appointed, which made for a very comfortable stay"
Australia
Casper
The price is NZ$782
includes taxes & fees
16 Jan - 17 Jan 2026
Dunes - elegant beach villa with huge swim spa
3.5 star property
10.0 out of 10, Exceptional, (3)
"We loved our family weekend in Port Fairy! The house is really nice and clean. Just a short drive away from amazing beaches and town. I would go back for sure. "
Canada
Marie-michele
The price is NZ$500
includes taxes & fees
26 Jan - 27 Jan 2026
Sails - Elegant, spacious beach villa
3.5 star property
9.6 out of 10, Exceptional, (176)
"It's a really beautiful property. I would definitely stay again. "
Australia
Vivien
The price is NZ$277
includes taxes & fees
11 Jan - 12 Jan 2026
Clonmara Country House & Cottages

Aparthotel in Port Fairy

Douglas Riverside
2.5 star property
9.4 out of 10, Exceptional, (14)
"A very pleasant stay Thankyou Jane"
Australia
Jeffrey John
The price is NZ$330
includes taxes & fees
6 Jan - 7 Jan 2026
Douglas Riverside

Cottage in Illowa

High View Family Cottages
3.0 star property
9.2 out of 10, Wonderful, (34)
"Clean, great location and easy checkin "
Australia
Nigel
The price is NZ$408
includes taxes & fees
12 Jan - 13 Jan 2026
High View Family Cottages
8.8 out of 10, Excellent, (5)
"Tucked down the driveway, this cottage is picture perfect. It has all you need for a weekend and is walking distance to lots of attractions. "
Australia
Courtney M.
The price is NZ$292
includes taxes & fees
12 Jan - 13 Jan 2026
5 Minute walk into the CBD near shops, restraunts and bars.

Aparthotel in Warrnambool

Quest Warrnambool
4.5 star property
9.2 out of 10, Wonderful, (790)
"Room was clean and staff were friendly "
Australia
Britt
The price is NZ$346
includes taxes & fees
2 Jan - 3 Jan 2026
Quest Warrnambool

Apartment in Port Fairy

The Victoria
4.0 star property
8.8 out of 10, Excellent, (765)
"Great stay"
Australia
Steven
The price is NZ$446
includes taxes & fees
13 Jan - 14 Jan 2026
The Victoria

Apartment in Warrnambool

Gallery Apartments
4.0 star property
9.6 out of 10, Exceptional, (369)
"Another amazing stay. Don't stay anywhere else but here when in Warrnambool. "
Australia
Anonymous traveller
The price is NZ$347
includes taxes & fees
5 Jan - 6 Jan 2026
Gallery Apartments

Apartment in Warrnambool

Apartments 521
3.0 star property
9.0 out of 10, Wonderful, (167)
"Very good apartment and very clean "
Australia
DAVID
The price is NZ$277
includes taxes & fees
12 Jan - 13 Jan 2026
Apartments 521

Apartment in Warrnambool

Botanic Racecourse Apartments
4.0 star property
9.8 out of 10, Exceptional, (14)
"Absolutely fantastic place. It included everything from foil to salt and pepper. Really appreciated the little details. It was also spotless. "
United Kingdom
Millie
Botanic Racecourse Apartments

Apartment in Warrnambool

Botanic City Apartments
4.0 star property
9.4 out of 10, Exceptional, (158)
"Great place, friendly staff and the best shower we had in our 2 weeks away. Definitely will be back if we stay in Warrnambool again."
Australia
Natalie
The price is NZ$407
includes taxes & fees
28 Dec - 29 Dec
Botanic City Apartments

Holiday Home in Warrnambool

Botanic Beach
4.0 star property
The price is NZ$1,178
includes taxes & fees
7 Jan - 8 Jan 2026
Botanic Beach
10.0 out of 10, Exceptional, (11)
"Great place for a family getaway. Being dog friendly was a huge bonus. "
Australia
Carmelo
The price is NZ$1,030
includes taxes & fees
2 Jan - 3 Jan 2026
Bluey House - three bedroom house with enclosed yard
10.0 out of 10, Exceptional, (3)
"This house is very modern and clean. Enjoy to stay."
Australia
phillip y.
The price is NZ$939
includes taxes & fees
26 Jan - 27 Jan 2026
Luxury 4-Bedroom Beach House | Ocean View | Smart Tech | Fully-Equipped Study
Lava House•WIFI•central heating/cooling•CBD

Holiday Home in Rosebrook

Lough View Cabin by Tiny Away
2.0 out of 10, (1)
The price is NZ$229
includes taxes & fees
13 Jan - 14 Jan 2026
Lough View Cabin by Tiny Away
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 Winslow Hotel Reviews

Find out more about Winslow

Everything you need to know about Winslow 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 Winslow 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 Winslow holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winslow holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winslow. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winslow 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 Winslow holiday rentals we have selected for you start as low as NZ$247 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winslow rentals

At Expedia, we put the best Winslow 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 Winslow 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 Winslow 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 Winslow. 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 a holiday rental in Winslow?

Yes, there are holiday rentals close to the most popular sights in Winslow, 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 Winslow has to offer?

River Lodge, Large house on the Hopkins River: This holiday home rental outside of Winslow is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Winslow?

While exploring the area, visit family-friendly sights like Flagstaff Hill Maritime Village, or get outside and enjoy nature at Port Fairy to Warrnambool Rail Trail. In the wider area, you’ll find Tower Hill Wildlife Reserve and Warrnambool Racecourse.

What’s a holiday rental in Winslow like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winslow. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip or a small group gathering.