Vacation Rentals in Windsor, Sydney: Compare 10+ Sites & Save

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55 Best Vacation Rentals in Windsor (Starting from $45)

T&V Suites
T&V Suites
Apartment
Windsor, Australia
0.3k from Windsor center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering

4 Bedrooms8 Guests
8.1

Very Good

304 reviews

$329
Average price / night
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Luxury House 5 Bedrooms River View
Luxury House 5 Bedrooms River View
House
Windsor, 2756, Australia
0.2k from Windsor center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

5 Bedrooms7 Guests
New to Booking
$550
Average price / night
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Secret River Cottage
Secret River Cottage
House
Windsor, Australia
0.4k from Windsor center

Accommodations, Parking, Homestays, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms5 Guests
New to Booking
$219
Average price / night
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3 Bedroom Heritage House Windsor
3 Bedroom Heritage House Windsor
House
Windsor, 2756, Australia
0.4k from Windsor center

AC, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$555
Average price / night
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Luxury House 5 bedrooms
Luxury House 5 bedrooms
Apartment
Windsor, Australia
0.6k from Windsor center

Apartments, Luxury, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family

5 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$465
Average price / night
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Comfy Ground-floor Ensuite Double Bed Room in welcoming Windsor with WiFi, AC
Comfy Ground-floor Ensuite Double Bed Room in welcoming Windsor with WiFi, AC
Ski Chalet
Windsor, 2756, Australia
0.5k from Windsor center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

1 Bedroom2 Guests
New to Booking
$126
Average price / night
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Windsor heritage house
Windsor heritage house
House
Windsor, Australia
0.6k from Windsor center

Balcony/Terrace, Security/Safety, Internet, Pet Friendly, Parking, Fireplace/Heating, Air Conditioner

3 Bedrooms6 Guests
New to Booking
$348
Average price / night
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Private Room in Charming Windsor with WiFi, AC, Washing Machine, Kitchenette
Private Room in Charming Windsor with WiFi, AC, Washing Machine, Kitchenette
Ski Chalet
Windsor, 2756, Australia
0.5k from Windsor center

AC, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$144
Average price / night
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Malniri Park by Tiny Away
Malniri Park by Tiny Away
House
Wilberforce, Australia
5.1k from Windsor center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom3 Guests
9.2

Superb

27 reviews

$142
Average price / night
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Stylish Cozy Swimming Pool Facing Self-Contained Room No 2 in delightful Windsor
Stylish Cozy Swimming Pool Facing Self-Contained Room No 2 in delightful Windsor
Ski Chalet
Windsor, 2756, Australia
0.6k from Windsor center

AC, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
6.0

Review score

1 reviews

$157
Average price / night
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King Cottage
King Cottage
House
Windsor, Australia
6.5k from Windsor center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms6 Guests
9.1

Superb

44 reviews

$98
Average price / night
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Top View Deluxe Self-Contained Room No 3 with Balcony Overlooking Swimming Pool.
Top View Deluxe Self-Contained Room No 3 with Balcony Overlooking Swimming Pool.
Apartment
Windsor, 2756, Australia
0.7k from Windsor center

AC, Balcony, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$210
Average price / night
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The River
The River
House
Wilberforce, Australia
7.7k from Windsor center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$506
Average price / night
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CORNWALLIS HOUSE Hawkesbury River\nBespoke Weddings,Events and Small Group Stays
CORNWALLIS HOUSE Hawkesbury River\nBespoke Weddings,Events and Small Group Stays
House
Cornwallis, 2756, Australia
2.8k from Windsor center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

4 Bedrooms8 Guests
10.0

Exceptional

96 reviews

$804
Average price / night
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Rooms at Gables in a modern home
Rooms at Gables in a modern home
House
Annangrove, Australia
7.8k from Windsor center

Cheap, Accommodations, Homestays, Lodgings, Places to stay

3 Bedrooms6 Guests
9.1

Superb

27 reviews

$45
Average price / night
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Cox's Cottage in the Hawkesbury Valley
Cox's Cottage in the Hawkesbury Valley
Cottage
Pitt Town, 2756, Australia
4.2k from Windsor center

AC, Barbecue, Breakfast Available, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.8

Exceptional

21 reviews

$138
Average price / night
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RedFlamesRetreat-Free WIFI & Parking-Walk to public transport-Quiet St & FamilyFriendly
RedFlamesRetreat-Free WIFI & Parking-Walk to public transport-Quiet St & FamilyFriendly
Apartment
Annangrove, Australia
7.8k from Windsor center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$153
Average price / night
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The Bunker - Malniri Park tranquil cabin accomodation
The Bunker - Malniri Park tranquil cabin accomodation
Cabin
Freemans Reach, 2756, Australia
4.9k from Windsor center

AC, No Smoking

1 Bedroom2 Guests
New to Booking
$256
Average price / night
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MaraylyaBox hillGables Specious 5Br Sweet House
MaraylyaBox hillGables Specious 5Br Sweet House
Villa
Australia
8.0k from Windsor center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Self-catering

5 Bedrooms10 Guests
8.0

Good

5 reviews

$227
Average price / night
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Come enjoy a farmstay at the historical Reibycroft Estate in Freemans Reach NSW.
Come enjoy a farmstay at the historical Reibycroft Estate in Freemans Reach NSW.
Cottage
Freemans Reach, 2756, Australia
5.0k from Windsor center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, Pool, Washer

2 Bedrooms4 Guests
New to Booking
$787
Average price / night
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Gables Box Hil Maraylya 2Br granny flat near parks
Gables Box Hil Maraylya 2Br granny flat near parks
House
Australia
8.0k from Windsor center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family, Self-catering

2 Bedrooms4 Guests
8.5

Very Good

2 reviews

$140
Average price / night
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High View Accommodation #6
High View Accommodation #6
Cottage
Freemans Reach, 2756, Australia
5.6k from Windsor center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$110
Average price / night
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High View Accommodations # 3
High View Accommodations # 3
Cottage
Freemans Reach, 2756, Australia
5.6k from Windsor center

AC, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$100
Average price / night
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High View Accommodation #1
High View Accommodation #1
Cottage
Freemans Reach, 2756, Australia
5.7k from Windsor center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
9.0

Fabulous

12 reviews

$100
Average price / night
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High View Accommodation #4
High View Accommodation #4
Cottage
Freemans Reach, 2756, Australia
5.7k from Windsor center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
9.2

Superb

22 reviews

$100
Average price / night
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High View Accommodation #2
High View Accommodation #2
Cottage
Freemans Reach, 2756, Australia
5.7k from Windsor center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
9.4

Superb

11 reviews

$100
Average price / night
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High View Accommodation #5
High View Accommodation #5
Cottage
Freemans Reach, 2756, Australia
5.7k from Windsor center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$121
Average price / night
Check Availability

Other accommodation types in Windsor:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Windsor.

Windsor Vacation Rentals on the Map

Frequently Asked Questions

You can explore 55 verified vacation rentals in Windsor. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Windsor vary depending on the season, property size, and location. Rates typically start from around $45 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Windsor include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Windsor welcome pets. Currently, 15 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Windsor often include amenities such as Fireplace/Heating, Laundry, and Balcony/Terrace. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.