Hillside Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Top Hillside Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Meadowmere Resort
CA $1,724
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Edmonton (YEA) to Portland (PWM)
8.6/10 Excellent! (1,005 reviews)
The lobby smelled like cigarettes additionally someone was smoking so close to our room outside that our room smelled like smoke.
Would not return.
Reviewed on Sep 5, 2026
Ready to book your vacation to Hillside?
Hillside Hotel Deals
Oxford Casino Hotel
777 Casino Way Oxford ME
Fully refundableReserve now, pay when you stay
CA $150
CA $163 total
Oct 7 - Oct 8
includes taxes & fees
The Poland Spring Resort
640 Maine Street Poland ME
CA $205
CA $224 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very good! (866 reviews)
"Our room was spacious, clean and comfortable. There was so much to do here but our stay was too short to try everything. I would come back here with my family again."
Reviewed on Sep 2, 2026
Dormir
965 Roosevelt Trail Windham ME
Fully refundableReserve now, pay when you stay
CA $260
CA $284 total
Sep 7 - Sep 8
includes taxes & fees
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 vacation package cost?
Offering great value package deals from CA $682 on Expedia, you'll be surprised at how little a vacation to Hillside costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Hillside?
You can usually find lower rates and better availability in January, February and March. Take a look at our cheap Hillside vacation packages and you could land some great off-season discounts.
How many days is enough for Hillside?
You can easily explore all the top sights in Hillside within a few days, including the must-see Steamboat Landing Mini Golf. If you're after a longer Hillside vacation, check out which kind of day trips and activities are available nearby.
How to find the best Hillside package deals?
Use Expedia's handy filters to find some tempting Hillside package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Hillside package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Hillside vacation as a package?
You can enjoy significant savings on your next Hillside break by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to browse the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Hillside?
If you're planning an impromptu Hillside 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 terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Hillside?
- Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Hillside.
- Set your budget: Factor in costs such as transportation, flights and meals when working out how much to put aside for your trip to Hillside. Then, select a property that matches your budget, whether that's a wallet-friendly option or a more upscale retreat.
- Determine how many days away: Start by listing all the sights and activities you want to get to in Hillside. Then, estimate how long you'll need for each, as well as any travel time.
- Bundle your accommodations and airfare: After you've settled on your travel dates and duration, lock in the right Hillside vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
