Winslow Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

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

    Plan, book, and manage your trip all in one place

Winslow Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Gladstone Grand Hotel

Gladstone Grand Hotel

2 out of 5
per person
20 Sept - 23 Sept
found 1 day ago
Return direct flight included
Singapore (SIN) to Timaru (TIU)
4.8/10 (9 reviews)
A beautiful old building in poor repair, could be really special. Dining area dingy and drab. Lack of information generally.

Reviewed on 29 Apr, 2025

Pinewood Motels

Pinewood Motels

3 out of 5
per person
20 Sept - 23 Sept
found 1 day ago
Return direct flight included
Singapore (SIN) to Timaru (TIU)
8.6/10 Excellent! (443 reviews)
Good. We just had to pay late check out

Reviewed on 29 Jun, 2025

Burkes Pass Country Motel

Burkes Pass Country Motel

2.5 out of 5
per person
20 Sept - 23 Sept
found 1 day ago
Return direct flight included
Singapore (SIN) to Timaru (TIU)
9.2/10 Wonderful! (193 reviews)
Loved this property. It was a short drive to Lake Tekapo for night sky viewing and cute pubs nearby for dinner. The property is great and the hosts are so lovely!

Reviewed on 27 Apr, 2025

Alpine Views Burkes Pass

Alpine Views Burkes Pass

3.5 out of 5
per person
20 Sept - 23 Sept
found 1 day ago
Return direct flight included
Singapore (SIN) to Timaru (TIU)
9.8/10 Exceptional! (55 reviews)
Lovely, warm, very clean accommodation.

Reviewed on 30 Jun, 2025

Top hotels in Winslow

Hotel Ashburton
Hotel Ashburton
3 out of 5
11 Racecourse Road, Ashburton
Fully refundableReserve now, pay when you stay
8/10 Very Good! (461 reviews)
"Very good and tidy"

Reviewed on 6 Jul, 2025

Get rates
Hotel Ashburton
Taylors Motel
Taylors Motel
3.5 out of 5
770 East Street, Ashburton
Fully refundableReserve now, pay when you stay
The price is S$126 per night from 28 Jul to 29 Jul
S$126
28 Jul - 29 Jul
includes taxes & fees
9.6/10 Exceptional! (352 reviews)
"All the things above. Room was on the smaller side"

Reviewed on 8 Jul, 2025

Taylors Motel
Academy Lodge Motel
Academy Lodge Motel
2 out of 5
782 East St, Ashburton, Canterbury
The price is S$89 per night from 15 Jul to 16 Jul
S$89
15 Jul - 16 Jul
includes taxes & fees
8.8/10 Excellent! (16 reviews)
"Cold on arrival.All services there."

Reviewed on 9 Jul, 2025

Academy Lodge Motel
See all 29 properties in Winslow
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 Winslow holiday package cost?
You can pick up a holiday package to this popular destination from S$1,570 on Expedia. However, how much your holiday to Winslow costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Winslow?
You can generally find reduced prices and greater availability in May, June and July. Take a look at our cheap Winslow holiday packages and you could get some great off-season discounts.
How many days is enough for Winslow?
With a well-planned itinerary, you can easily tick off the most popular Winslow attractions in a handful of days. But if you want to discover lesser-known spots or go on day trips, consider booking your Winslow holiday for longer.
How to find the best Winslow package deals?
Finding a cheap Winslow package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Winslow package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Winslow holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still get the flexibility to create a personalised Winslow holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Winslow?
If you're planning an impromptu Winslow holiday, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Winslow?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Winslow.
  2. Set your budget: Consider expenses such as flights, food and transportation when working out how much to set aside for your trip to Winslow. Then, choose a hotel that works with your budget, whether that's a wallet-friendly option or a high-end getaway.
  3. Decide how long to go away for: Now that you're up to speed on Winslow, you can figure out the perfect length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Combine your airfare and accommodation: Once you've nailed down your travel dates and duration, book the right Winslow holiday package for you.

* 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.