Hillside Vacations from $327

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Your Hillside Vacation

With everything organized before you head off, our Hillside vacation packages mean you can simply focus on having a good time! One neighborhood to consider staying in this fascinating city is North Sebago, which is great for camping and views. If seeing the sights is on your list of things to do during your trip to Hillside, find your way to major attractions like Wards Cove. No matter your travel plans or budget, organizing a tailored Hillside vacation is easy with Expedia.

The Latest Hillside vacation packages

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $570, price is now $327 per person
$327
per person
Jan 15 - Jan 19
found 3 hours ago
Roundtrip flight included
Miami (MIA) to Portland (PWM)
9.2/10 Wonderful! (1,621 reviews)
Beautiful hotel in Old Port area! Great location for shopping, restaurants and walking around. Staff was amazing.

Reviewed on Nov 10, 2025

The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Downtown Portland
Save 100% on your flight
Price was $765, price is now $476 per person
$476
per person
Jan 15 - Jan 19
found 3 hours ago
Roundtrip flight included
Miami (MIA) to Portland (PWM)
No reviews
Really nice and clean new hotel!

Reviewed on Oct 27, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $648, price is now $470 per person
$470
per person
Jan 15 - Jan 19
found 3 hours ago
Roundtrip flight included
Miami (MIA) to Portland (PWM)
9.6/10 Exceptional! (239 reviews)
Cleanliness, staff in lobby were helpful.

Reviewed on Oct 28, 2025

The Wolfeboro Inn

The Wolfeboro Inn

3.5 out of 5
Price was $1,439, price is now $1,090 per person
$1,090
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
8.2/10 Very Good! (538 reviews)
Hotel is located in a great spot, easy to walk to town. Room was nice and clean. It looked like the property needed overall maintenance. Lots of flaking paint and wood rot.

Reviewed on Oct 22, 2025

Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3 out of 5
Downtown Portland
Save 100% on your flight
Price was $520, price is now $396 per person
$396
per person
Jan 15 - Jan 19
found 3 hours ago
Roundtrip flight included
Miami (MIA) to Portland (PWM)
9.2/10 Wonderful! (1,016 reviews)
Pleasant staff. Very clean. Hot tub did not work. Parking is an added extra. Worth it but know that it's not included.

Reviewed on Nov 10, 2025

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Discover the most popular places to visit in Hillside

Long Beach Marina

Explore the waterfront in Sebago with a trip to Long Beach Marina. Wander the lakeside in this family-friendly area.

Long Beach Marina

Hillside Hotel Deals

Dormir

Dormir

3 out of 5
965 Roosevelt Trail, Windham, ME
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $101 total per night from Nov 12 to Nov 13
$101 total
Nov 12 - Nov 13
Total with taxes and fees
8.8/10 Excellent! (1,015 reviews)
Great hotel, I am glad I picked them. The room was comfortable and updated. Rooms do include a refrigerator and microwave.

Reviewed on Nov 5, 2025

Dormir
Oxford Casino Hotel

Oxford Casino Hotel

3 out of 5
777 Casino Way, Oxford, ME
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $136 total per night from Nov 12 to Nov 13
$136 total
Nov 12 - Nov 13
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Clean and decent room. Comfortable bed and pillows.

Reviewed on Oct 29, 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
$87 nightly
The price is $95 total per night from Nov 19 to Nov 20
$95 total
Nov 19 - Nov 20
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
Everything. Awesome staff. clean room, great breakfast food.

Reviewed on Nov 9, 2025

Hampton Inn Oxford
See all 1,277 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.

Find the Best Hillside Vacation Packages

Hillside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Top Sights
Long Beach Marina and Wards Cove

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Frequently asked questions

How much does a Hillside vacation package cost?
You'll find cheap prices from $327 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 vacation to Hillside costs.
What are the cheapest months to go to Hillside?
You're likely to find lower rates and greater availability in November, December and January. Take a look at our cheap Hillside vacation packages and you could score some great off-season discounts.
How many days is enough for Hillside?
The ideal length of your Hillside vacation depends on what you'd like to see. Usually, a few days to a week will give you time to check out all the main attractions and explore some hidden spots along the way.
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 personalize your search by "Amenities," "Property type," "Traveler 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 vacation as a package?
Expedia vacation 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 personalized Hillside vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Hillside vacation packages?
Your Hillside getaway should be a relaxing escape from your busy life, not a reason for money-related stress. So to give you that extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.