Hillside 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 Hillside

Dormir

Dormir

3 out of 5
965 Roosevelt Trail, Windham, ME
Fully refundableReserve now, pay when you stay
The price is S$324 per night from 13 Aug to 14 Aug
S$324
13 Aug - 14 Aug
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"I like the cleanliness. I do wish that for the price, room cleaning/replenishing towels, was available. Currently have to bring dirty towels down, in order to get clean ones."

Reviewed on 5 Aug, 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 S$200 per night from 1 Sept to 2 Sept
S$200
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Very professional staff and easy, plentiful free parking. Room was very spacious, clean and had all the amenities needed."

Reviewed on 28 Jul, 2025

Oxford Casino Hotel
The Poland Spring Resort

The Poland Spring Resort

3.5 out of 5
640 Maine Street, Poland, ME
The price is S$180 per night from 13 Aug to 14 Aug
S$180
13 Aug - 14 Aug
includes taxes & fees
7.8/10 Good! (774 reviews)
"Everything was lovely. I loved staying here"

Reviewed on 2 Aug, 2025

The Poland Spring Resort
See all 1,346 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. 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.