Hillside Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Hillside Holiday
Our pick of the best Hillside Hotel Deals
Oxford Casino Hotel
777 Casino Way Oxford ME
Fully refundableReserve now, pay when you stay
NZ$218
23 Aug - 24 Aug
includes taxes & fees
The Poland Spring Resort
640 Maine Street Poland ME
NZ$274
16 Aug - 17 Aug
includes taxes & fees
8/10 Very good! (856 reviews)
"Loved the cottage! Everything was there including everything for the lake."
Reviewed on 13 Aug 2026
Dormir
965 Roosevelt Trail Windham ME
Fully refundableReserve now, pay when you stay
NZ$384
27 Aug - 28 Aug
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"overall for anyone needing a quick overnight in the area close to lake sebago it works well. They have limited amenities, tv in the room is basic cable only not a smart tv and most of the channels are sports channels. They don’t refresh towels or clean rooms unless you ask. lighting in the room is ..."
Reviewed on 14 Aug 2026
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.
Stay near popular Hillside attractions
Wards Cove
8.0/10 (1 review)
Commune with nature and explore the great outdoors at Wards Cove during your travels in Hillside.
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?
- 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.
- 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.
- 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.
- 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.
