Windermere Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 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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    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
Save 100% on your flight
Price was S$2,062, price is now S$1,298 per person
S$1,298
per person
20 Feb - 25 Feb
found 15 hours ago
Return flight included
Singapore (SIN) to Sydney (SYD)
8.2/10 Very Good! (2,388 reviews)
Clean place and receptionist are very helpful and very accessible to everything.

Reviewed on 29 Dec, 2025

InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
Save 100% on your flight
Price was S$3,573, price is now S$2,304 per person
S$2,304
per person
19 Feb - 26 Feb
found 15 hours ago
Return flight included
Singapore (SIN) to Sydney (SYD)
9/10 Wonderful! (596 reviews)
Initial room was sub standard with mol

Reviewed on 13 Dec, 2025

Rydges World Square

Rydges World Square

4.5 out of 5
Sydney Central Business District
Save 100% on your flight
Price was S$2,315, price is now S$1,644 per person
S$1,644
per person
19 Feb - 26 Feb
found 15 hours ago
Return flight included
Singapore (SIN) to Sydney (SYD)
8.8/10 Excellent! (1,257 reviews)
Staff were friendly. No room for early check in until 2pm. Noisy on the Pitts St side with motorcycles and hot rod engine noises. Great locations for restaurants and shopping. There are flying bugs from the ground drain in the bathroom. Our room did not get a refresh on one day.

Reviewed on 23 Dec, 2025

Stylish 2-bed Apartment With BBQ Patio Near Beach

Stylish 2-bed Apartment With BBQ Patio Near Beach

2.5 out of 5
Coogee
Price was S$2,073, price is now S$1,523 per person
S$1,523
per person
20 Feb - 25 Feb
found 15 hours ago
Return flight included
Singapore (SIN) to Sydney (SYD)
No reviews
Central 2-bed With Parking & Stunning Views

Central 2-bed With Parking & Stunning Views

2.5 out of 5
Parramatta
Price was S$1,980, price is now S$1,466 per person
S$1,466
per person
20 Feb - 25 Feb
found 15 hours ago
Return flight included
Singapore (SIN) to Sydney (SYD)
No reviews

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

Top hotels in Windermere

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 S$177 per night from 18 Jan to 19 Jan
S$177
18 Jan - 19 Jan, 2026
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
One of our pillows is mouldy. We only realise the morning we woke up and we saw the end of the pillow. The body wash in the shower is empty. My 5yr old daughter burn her ankle in the baby jumping castle when she did her first slide. So she did not get to enjoy much as she had pain on her foot. We ...

Reviewed on 24 Dec, 2025

Rydges Resort Hunter Valley
Harrigan's Hunter Valley

Harrigan's Hunter Valley

4 out of 5
2090 Broke Rd Pokolbin NSW
The price is S$163 per night from 5 Jan to 6 Jan
S$163
5 Jan - 6 Jan, 2026
includes taxes & fees
8.2/10 Very Good! (995 reviews)
Room was comfortable and clean. Easy parking and very convenient location to the gardens

Reviewed on 25 Dec, 2025

Harrigan's Hunter Valley
Oaks Cypress Lakes Resort

Oaks Cypress Lakes Resort

4 out of 5
15 Thompsons Road Pokolbin NSW
Fully refundableReserve now, pay when you stay
The price is S$188 per night from 12 Jan to 13 Jan
S$188
12 Jan - 13 Jan, 2026
includes taxes & fees
8.4/10 Very Good! (2,219 reviews)
The room was great. Very roomy. The resort was nice and quiet. The pools were great. We'll be back

Reviewed on 23 Dec, 2025

Oaks Cypress Lakes Resort
See all 872 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.

Frequently asked questions

How much does a Windermere holiday package cost?
We make it easy to see the world, with Windermere holiday packages starting from as low as S$1,298. 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 holiday 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 holiday 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 holiday?
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 holiday package?
With a holiday 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 holiday 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

Newcastle: Lake Macquarie Cruise with Lunch

Newcastle: Lake Macquarie Cruise with Lunch

S$60
per adult
Newcastle: Lake Macquarie Cruise with Lunch
Hunter Valley - Awaken your senses with chocolate, cheese & wine

Sydney: Hunter Valley Wines, 2 Course Lunch, Cheese & Choc Tour

S$190
per adult
Sydney: Hunter Valley Wines, 2 Course Lunch, Cheese & Choc Tour
Cheeses of the World Masterclass

Cheeses of the World Masterclass

S$34
per adult
100% of travellers recommend
Cheeses of the World Masterclass
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.