Hillside Holidays from AU$1,980

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The Latest Hillside Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
per person
26 Sept - 30 Sept
found 24 hours ago
Return direct flight included
Sydney (SYD) to Portland (PWM)
7.8/10 Good! (1,032 reviews)
Staff was wonderful!

Reviewed on 20 Jul. 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
per person
26 Sept - 30 Sept
found 24 hours ago
Return direct flight included
Sydney (SYD) to Portland (PWM)
9.4/10 Exceptional! (1,008 reviews)
everything very clean, wonderful place.

Reviewed on 19 Jul. 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
26 Sept - 30 Sept
found 24 hours ago
Return direct flight included
Sydney (SYD) to Portland (PWM)
9.2/10 Wonderful! (1,523 reviews)
Excellent location and walking distance to stores, restaurants and waterfront trail. We loved the courtyard where you can eat a meal. Breakfast at on-site restaurant was very good. The snack and beverage stations on every floor were great, too.

Reviewed on 20 Jul. 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
per person
26 Sept - 30 Sept
found 24 hours ago
Return direct flight included
Sydney (SYD) to Portland (PWM)
9.4/10 Exceptional! (591 reviews)
The team made the stay for us. Really nice, genuine and people. Special mention for the way breakfast is served and a shout out for the breakfast sandwiches and baked eggs! Great location for an easy walk into town and for longer walks along the coast.

Reviewed on 17 Jul. 2025

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
per person
26 Sept - 30 Sept
found 24 hours ago
Return direct flight included
Sydney (SYD) to Portland (PWM)
9.4/10 Exceptional! (1,338 reviews)
Always a nice stay here. We had a hard travel day and the staff made every effort to make us feel more comfortable. Great location and easy valet parking. Friendly staff.

Reviewed on 20 Jul. 2025

Hillside Holiday

Hillside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Sebago Lake State Park, Shawnee Peak and Deertrees Theatre and Cultural Centre

Our pick of the best Hillside Hotel Deals

Dormir

Dormir

3 out of 5
965 Roosevelt Trail, Windham, ME
Fully refundableReserve now, pay when you stay
The price is AU$387 per night from 23 July to 24 July
AU$387
23 July - 24 July
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"We were so happy that we will stay again."

Reviewed on 11 Jul. 2025

Dormir
Oxford Casino Hotel

Oxford Casino Hotel

3 out of 5
777 Casino Way, Oxford, ME
Fully refundableReserve now, pay when you stay
The price is AU$240 per night from 4 Aug to 5 Aug
AU$240
4 Aug - 5 Aug
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"I liked the staff and the affordability"

Reviewed on 19 Jul. 2025

Oxford Casino Hotel
Hampton Inn Oxford

Hampton Inn Oxford

2.5 out of 5
151 Main St, Oxford, ME
Fully refundableReserve now, pay when you stay
The price is AU$214 per night from 28 July to 29 July
AU$214
28 July - 29 July
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"This was the fourth year in a row to stay at the Hampton Inn Oxford on my vacation. The staff is always very friendly and helpful and the room is very clean and spacious. The free breakfast is great with many different choices. Most importantly the Oxford casino is right across the street. I will ..."

Reviewed on 17 Jul. 2025

Hampton Inn Oxford
See all 1,367 properties in Hillside
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 a Hillside holiday package cost?
You'll find cheap prices from AU$1,980 on Expedia for your Hillside escape. However, factors like the length of stay, the season and your choice of hotel will influence how much your holiday to Hillside costs.
What are the cheapest months to go to Hillside?
January, February and March are great times to search for cheap Hillside holiday packages. Travelling in less busy months means you can generally find reduced prices on accommodation and flights.
How many days is enough for Hillside?
Usually, a handful of days is enough to explore the top attractions during your Hillside holiday. However, if you want to have more time to rest or go on day trips, consider extending your itinerary.
How to find the best Hillside package deals?
Bagging a cheap Hillside package deal is easy with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can personalise your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most affordable Hillside package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Hillside holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still have the flexibility to create a personalised Hillside holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Hillside?
If you have your Hillside travel dates locked in, book as early as you can to bag some unbeatable deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Hillside?

  1. Choose when to get away: Check your calendar and get your bags packed. Your favourite season and the type of activities available will also help you decide when to escape to Hillside.
  2. Plan your budget wisely: As well as the price of your hotel, you'll need to factor in other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Hillside.
  3. Determine how many days away: Start by making a list of all the activities and attractions you'd like to get to in Hillside. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to pick a Hillside holiday package that brings all your bookings together.

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