Winslow Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Winslow

Baymont by Wyndham Dale
Baymont by Wyndham Dale
2.5 out of 5
1339 N Washington St, Dale, IN
Fully refundableReserve now, pay when you stay
The price is S$170 per night from 30 Jun to 1 Jul
S$170
30 Jun - 1 Jul
includes taxes & fees
6.6/10 (1,001 reviews)
"I reserved two rooms for a family get together a trip at Holiday World it had a great location our room was clean very comfortable the staff was friendly breakfast was basic could have used a few more fresher items but overall our stay was great"

Reviewed on 15 Jun, 2025

Baymont by Wyndham Dale
Comfort Inn
Comfort Inn
2.5 out of 5
123 Scenic Hills Court, Ferdinand, IN
Fully refundableReserve now, pay when you stay
The price is S$169 per night from 6 Jul to 7 Jul
S$169
6 Jul - 7 Jul
includes taxes & fees
8.4/10 Very Good! (481 reviews)
"Easy access to Highways, close to Holiday World and cute towns around the area"

Reviewed on 16 Jun, 2025

Comfort Inn
Fairfield Inn & Suites Jasper
Fairfield Inn & Suites Jasper
2.5 out of 5
333 River Centre Landing, Jasper, IN
Fully refundableReserve now, pay when you stay
The price is S$211 per night from 10 Jul to 11 Jul
S$211
10 Jul - 11 Jul
includes taxes & fees
9.2/10 Wonderful! (345 reviews)
"Best hotel in Jasper"

Reviewed on 8 Jun, 2025

Fairfield Inn & Suites Jasper
See all 82 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 snap up a holiday package to this top destination on Expedia. However, how much your holiday to Winslow costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Winslow?
You can usually find lower prices and greater availability in January, February and November. Browse our cheap Winslow holiday packages and you could get some excellent off-season deals.
How many days is enough for Winslow?
The ideal duration for your Winslow holiday depends on what you'd like to see and do. Generally, a few days to a week will give you plenty of time to tick off all the leading attractions and discover some hidden gems along the way.
How to find the best Winslow package deals?
Use Expedia's filter tool to help you find some great Winslow package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Winslow package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your holiday package well in advance.
Is it cheaper to book a Winslow holiday as a package?
You can enjoy significant savings on your next Winslow break by booking a personalised holiday package. Check the "Package" heading, then select your destination and travel dates to see the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Winslow?
If you're considering a spontaneous Winslow trip, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Winslow?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred time of year and the activities on offer will also help you decide when to escape to Winslow.
  2. Set a budget: Factor in expenses like food, flights and transportation when calculating how much to set aside for your trip to Winslow. Then, choose a property that suits your budget, whether that's a wallet-friendly stay or a high-end retreat.
  3. Decide how long to go away for: Now that you're more familiar with Winslow, you can work out the right length of your holiday. Pull together a draft itinerary and allocate enough time to cover everything you want to do.
  4. Combine your accommodation and airfare: Once you've settled on your travel dates and duration, lock in the perfect 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.