Hillside Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Save up to NZ$616 when you book a flight and hotel together*
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    Plan, book, and manage your trip all in one place

Hillside Holiday

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 NZ$419 per night from 14 July to 15 July
NZ$419
14 July - 15 July
includes taxes & fees
8.8/10 Excellent! (1,004 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 NZ$249 per night from 14 July to 15 July
NZ$249
14 July - 15 July
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Great staff is amazing!"

Reviewed on 23 Jun. 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 NZ$231 per night from 27 July to 28 July
NZ$231
27 July - 28 July
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Very clean, friendly staff, and awesome breakfast."

Reviewed on 11 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.

Frequently asked questions

How much does a Hillside holiday package cost?
You'll find cheap prices 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.