Oak Hill Holidays from AU$2,249

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Your Oak Hill Holiday

Take away the hard part of organising your next epic adventure with an Oak Hill holiday package. Whether you're lured here by its history, food or other highlights, there's an inexhaustible array of experiences to be had. If some sightseeing is on your list of things to do during your trip to Oak Hill, stop by major attractions such as Palmyra Beach. Expedia is here to help you escape your routine. Tailor your holiday to Oak Hill to suit your style of travel, whatever that may be.

The Latest Oak Hill Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.8/10 Excellent! (2,250 reviews)
Great stay, shuttle to the airport was timely

Reviewed on 9 Aug. 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.2/10 Very Good! (2,084 reviews)
The room was comfortable and very quiet despite the proximity to the airport. I would have preferred a queen size bed, but the only available option was a double.

Reviewed on 9 Aug. 2025

Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
O'Hare
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.6/10 Excellent! (1,537 reviews)
Sonesta was lovely. Easy check in. Nice room. Pillows not so great. Shuttle service was excellent as was all the staff!

Reviewed on 8 Aug. 2025

DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
7.4/10 Good! (1,009 reviews)
Very very quiet slept so good Needed pool and gym and cooking for myself

Reviewed on 7 Aug. 2025

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.8/10 Excellent! (1,001 reviews)
Clean and quiet. Great location and close to ORD

Reviewed on 6 Aug. 2025

Oak Hill Holiday

Oak Hill Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
-3.89ºC
Max Temp Summer
24ºC

Our pick of the best Oak Hill Hotel Deals

The Ingleside Hotel

The Ingleside Hotel

4 out of 5
2810 Golf Road, Pewaukee, WI
Fully refundableReserve now, pay when you stay
The price is AU$167 per night from 24 Aug to 25 Aug
AU$167
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (671 reviews)
"Very nice staff and clean rooms. Comfortable beds!"

Reviewed on 31 Jul. 2025

The Ingleside Hotel
Best Western Waukesha Grand

Best Western Waukesha Grand

2.5 out of 5
2840 N Grandview Boulevard, Pewaukee, WI
Fully refundableReserve now, pay when you stay
The price is AU$133 per night from 17 Aug to 18 Aug
AU$133
17 Aug - 18 Aug
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"The property was well maintained, the breakfast buffet was excellent! And the staff was wonderful."

Reviewed on 3 Aug. 2025

Best Western Waukesha Grand
AmericInn by Wyndham Delafield-Waukesha-Milwaukee

AmericInn by Wyndham Delafield-Waukesha-Milwaukee

2.5 out of 5
2412 Milwaukee St, Delafield, WI
Fully refundableReserve now, pay when you stay
The price is AU$154 per night from 11 Aug to 12 Aug
AU$154
11 Aug - 12 Aug
includes taxes & fees
8/10 Very Good! (647 reviews)
"Good value for the price, seems like a safe area"

Reviewed on 6 Aug. 2025

AmericInn by Wyndham Delafield-Waukesha-Milwaukee
See all 235 properties in Oak Hill
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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does an Oak Hill holiday package cost?
You can snap up a holiday package to this popular destination from AU$2,249 on Expedia. However, how much your holiday to Oak Hill costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Oak Hill?
If you're hoping to snag a cheap Oak Hill holiday package, consider visiting in January, February and November. You'll generally find lower prices on hotels and airfares during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Oak Hill?
With a well-organised schedule, you can easily visit the most popular Oak Hill attractions in a handful of days. But if you want to explore off the beaten track or go on day trips, think about booking your Oak Hill holiday for longer.
How to find the best Oak Hill package deals?
Landing a cheap Oak Hill package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most affordable Oak Hill package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Oak Hill holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking hotels and flights separately. Better still, you can personalise your Oak Hill trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Oak Hill?
If you're planning a spur-of-the-moment Oak Hill adventure, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Oak Hill?

  1. Pick your dates: What you want to do in Oak Hill and your favourite season can help you decide when to go.
  2. Figure out your budget: Ensure you have enough money to pay for everything from dining out and transportation to flights and experiences. Your hotel will probably be the largest expense during your trip to Oak Hill.
  3. Decide your trip length: Think about how much time you'd like to spend discovering Oak Hill. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalised Oak Hill holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.