Windermere Holidays

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Price found within the past 48 hours. Click for updated prices.
Novotel Sydney Darling Square

Novotel Sydney Darling Square

4.5 out of 5
Sydney Central Business District
per person
20 Aug - 24 Aug
found 7 hours ago
Return flight included
Singapore (SIN) to Sydney (SYD)
8.8/10 Excellent! (1,008 reviews)
Thank you for such a memorable stay. The team arranged for my daughter and I to stay in an accessible room due to her leg injury and the use of a wheelchair without me having to request it. We loved our 2 night stay and will definitely be back. Reception staff also arranged for a lovely birthday card to be left in the room for my daughter, which was such a thoughtful touch. Staff were able to give great recommendations for things to do and places to eat nearby. We will definitely back for our next staycation!

Reviewed on 12 Jul, 2025

Rydges Sydney Central

Rydges Sydney Central

4.5 out of 5
Surry Hills
per person
20 Aug - 24 Aug
found 7 hours ago
Return flight included
Singapore (SIN) to Sydney (SYD)
8.6/10 Excellent! (1,006 reviews)
It was a perfect place to stay. Thank you.

Reviewed on 18 Jul, 2025

InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
per person
20 Aug - 24 Aug
found 7 hours ago
Return flight included
Singapore (SIN) to Sydney (SYD)
9/10 Wonderful! (570 reviews)
wonderful get away, five star experience. Breakfast is a must!

Reviewed on 24 Jun, 2025

The Ultimo

The Ultimo

4 out of 5
Haymarket
per person
20 Aug - 24 Aug
found 7 hours ago
Return flight included
Singapore (SIN) to Sydney (SYD)
8.8/10 Excellent! (1,000 reviews)
Staff were excellent. Room faced onto very noisy street at night ( car racing) & unfortunately hotel undergoing renovations ( jack hammers, builders noise). We were advised of this AFTER our booking was made

Reviewed on 2 Jun, 2025

Hotel Woolstore 1888, Sydney - Handwritten Collection

Hotel Woolstore 1888, Sydney - Handwritten Collection

4 out of 5
Pyrmont
per person
20 Aug - 24 Aug
found 7 hours ago
Return flight included
Singapore (SIN) to Sydney (SYD)
9.2/10 Wonderful! (1,001 reviews)
Quirky place inside but great staff and good rooms. Very well located with parking right across the road. Easy walk to Barangaroo and there is a metro station really close as well. Been there before and will return for any city stays.

Reviewed on 3 Jul, 2025

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
The price is S$191 per night from 27 Jul to 28 Jul
S$191
27 Jul - 28 Jul
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Very kind staff"

Reviewed on 17 Jul, 2025

Rydges Resort Hunter Valley
Chateau Elan At The Vintage

Chateau Elan At The Vintage

5 out of 5
Vintage Drive, Hunter Valley, Pokolbin, NSW
Fully refundableReserve now, pay when you stay
The price is S$175 per night from 21 Jul to 22 Jul
S$175
21 Jul - 22 Jul
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Beautifully presented hotel and grounds. Good golf course. Very friendly and helpful staff. Good buffet breakfast. Bathrooms in rooms badly need updating with cracked basins and tiles and shower doors that won't close. Also the TV's need updating as it is almost impossible to connect personal streaming ..."

Reviewed on 16 Jul, 2025

Chateau Elan At The Vintage
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$158 per night from 23 Jul to 24 Jul
S$158
23 Jul - 24 Jul
includes taxes & fees
8.4/10 Very Good! (2,161 reviews)
"Great location but the rooms (in particular the bathroom) was tired looking."

Reviewed on 13 Jul, 2025

Oaks Cypress Lakes Resort
See all 898 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$841. 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

Wine Tasting Fun

Hunter Valley Small Group Luxury Wine Tasting Tour from Sydney

S$195
per adult
Hunter Valley Small Group Luxury Wine Tasting Tour from Sydney
Maitland's True Crime Tour

Maitland's True Crime Tour

S$29
per adult
Maitland's True Crime Tour
Country towns: River & farm tour. Departing Newcastle.

Country towns: River & farm tour. Departing Newcastle.

S$206
per adult
Country towns: River & farm tour. Departing Newcastle.
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.