Windermere Vacation Packages

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    Save up to CA $750 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Holiday Package Deals in Windermere

Price found within the past 48 hours. Click for updated prices.
Woolwich Studio Bliss, Private Oasis by the Water

Woolwich Studio Bliss, Private Oasis by the Water

2.5 out of 5
Woolwich
Price was CA $3,142, price is now CA $2,780 per person
CA $2,780
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
8/10 Very Good! (1 review)
Live in the Heart of Surry Hills - Walk to City

Live in the Heart of Surry Hills - Walk to City

2.5 out of 5
Surry Hills
Price was CA $3,356, price is now CA $2,889 per person
CA $2,889
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
8/10 Very Good! (2 reviews)
Serene Studio With Balcony in Prime Location

Serene Studio With Balcony in Prime Location

2.5 out of 5
Wollstonecraft
Price was CA $3,277, price is now CA $2,850 per person
CA $2,850
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
No reviews
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
Price was CA $3,338, price is now CA $2,914 per person
CA $2,914
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
8.2/10 Very Good! (2,661 reviews)
The staff are very helpful specially the one who clean our room.

Reviewed on Apr 21, 2026

Coogee Bay Boutique Hotel

Coogee Bay Boutique Hotel

4 out of 5
Coogee
Price was CA $3,587, price is now CA $3,206 per person
CA $3,206
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
8.8/10 Excellent! (868 reviews)
Beautiful view of the water. Quiet location. Beautiful decor in rooms. Staff very helpful. Clean & tidy rooms & bathroom. Unfortunately no exhaust fan in bathroom & the bed was very hard (but that’s just me)! Close to Coogee shops & beach Would definitely stay again.

Reviewed on Apr 19, 2026

Where to stay in Windermere

Find the best Windermere areas and neighborhoods for the activities you enjoy most. Learn more about Windermere
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Raymond Terrace

1 out of top 10 points of interest in this area

Unique features of Raymond Terrace include the restaurants and shopping. Make a stop by Nargoon Reserve or Tilligerry State Conservation Area while you're exploring the area.

Find hotels in Raymond Terrace

Windermere Hotel Deals

Rydges Resort Hunter Valley

Rydges Resort Hunter Valley

4 out of 5
430 Wine Country Drive Lovedale NSW
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from May 7 to May 8
CA $179
CA $197 total
May 7 - May 8
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Wonderful place to stay at

Reviewed on Apr 21, 2026

Rydges Resort Hunter Valley
Harrigan's Hunter Valley

Harrigan's Hunter Valley

4 out of 5
2090 Broke Rd Pokolbin NSW
The price is CA $128 per night from May 7 to May 8
CA $128
CA $141 total
May 7 - May 8
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
Lovely huge 2 bedroom apartment. A bit dated but super roomy, private, and comfortable with full amenities and an excellent outdoor area and outlook.

Reviewed on Apr 20, 2026

Harrigan's Hunter Valley
Oaks Cypress Lakes Resort

Oaks Cypress Lakes Resort

4 out of 5
15 Thompsons Road Pokolbin NSW
The price is CA $194 per night from Apr 27 to Apr 28
CA $194
CA $194 total
Apr 27 - Apr 28
includes taxes & fees
8.4/10 Very Good! (2,263 reviews)
Cypress Lakes resort is brilliantly located. The room we were in was just a little dated and tired (especially the bathroom) but still fine and comfortable. Having two single beds put together for the bed was also just a little unexpected. But the one thing which brought the rating down to 4 rather ...

Reviewed on Apr 19, 2026

Oaks Cypress Lakes Resort
See all 844 properties in Windermere
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.
All Inclusive Vacations
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Beach Vacations
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Frequently asked questions

How much does a Windermere vacation package cost?
We make it easy to see the world, with Windermere vacation packages starting from as low as CA $2,780. You'll have the flexibility to bundle your preferred airlines, hotels and car rental. For the ultimate escape, why not add a few tours and activities to your itinerary?
How do I get a cheap travel package to Windermere?
Combine your flight and hotel bookings, add extras such as tours, and save with a Windermere vacation package. You won't just pick up superb discounts on your getaway — you'll have lots of choice at your fingertips too. When you book through Expedia, you can select from more than 550 airlines and 1,000,000 hotels throughout the world. Your affordable vacation starts right here, right now!
What are the top hotels in Windermere?
When it comes to comfy and convenient places to stay in Windermere, you can't beat Lochinvar Cottage Hunter Valley - Pet Friendly. Browse our offers and score a great price.
How far in advance should I book my Windermere vacation?
To bag discount prices, book nice and early. Airlines typically begin selling tickets, along with some of the lowest fares, around a year ahead of time. Hotels, activities and car rental should also be booked early to avoid disappointment. If you've decided on a last-minute getaway in Windermere, there are always plenty of great bargains to be had on Expedia. Book something in today!
What does an Expedia Windermere travel package include?
Flights, rental cars and hotels, or any combination of them — it's totally up to you. Whether you're venturing to Windermere with the whole family or adventuring with your friends, there's a bundle to suit every budget and style. Once you've made your booking, why not add on a few activities?
What should I know before booking a Windermere travel package?
You'll land terrific savings when you combine your hotels, flights and rental cars into a travel package. Not only that, booking everything in one spot simply makes planning easier. So why waste time or money? Whether you're putting together a ritzy city getaway or a low-cost family break, take a look at our package deals today.
Can I choose my airline with a Windermere Expedia vacation package?
With a vacation package, you're always in charge. Whether you want to fly to Windermere in coach or first class, simply choose from the available airline options. Expedia has access to more than 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Windermere vacation package?
Because we understand life can throw you a few curveballs, the answer is yes. To find out more, head to our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it without penalty. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

Things to do

Enjoy an amazing day out with friends

Hunter Valley Wine Tasting Tour from Sydney

CA $225
per adult
100% of travellers recommend
Hunter Valley Wine Tasting Tour from Sydney
Newcastle: Lake Macquarie Cruise with Lunch

Lake Macquarie: Cruise with Lunch on the Lake

CA $83
per adult
100% of travellers recommend
Lake Macquarie: Cruise with Lunch on the Lake
Picture 8 for Activity Maitland's True Crime Tour

Maitland's True Crime Tour

CA $33
per adult
100% of travellers recommend
Maitland's True Crime Tour
See all activities in Maitland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.