Hillside Vacations from $511

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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.
InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was $656, price is now $511 per person
$511
per person
Feb 1 - Feb 7
found 2 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Portland (PWM)
9.4/10 Exceptional! (356 reviews)
Pool was fine; unfortunately sauna was not working.

Reviewed on Dec 2, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $673, price is now $531 per person
$531
per person
Feb 12 - Feb 15
found 18 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Waitress was alone and overworked, we waited a long time for coffee and silverware

Reviewed on Dec 31, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,061, price is now $840 per person
$840
per person
Feb 12 - Feb 15
found 18 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
The property is beautiful, the staff is kind, and the rooms are spacious and clean. It was great to have a safe place to park the car while having so many things to do within walking distance. Being able to grab a quick breakfast before heading out was great too! We loved our stay here!

Reviewed on Nov 23, 2025

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was $696, price is now $555 per person
$555
per person
Feb 12 - Feb 15
found 18 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Portland (PWM)
9.4/10 Exceptional! (1,512 reviews)
The hotel has that old fashioned quiet atmosphere with unobtrusive but attentive staff members. It is quietly and comfortably luxurious, perfect for exploring downtown on foot and within a short distance of most interesting restaurants

Reviewed on Dec 31, 2025

The Kennebunk Inn

The Kennebunk Inn

2.5 out of 5
Price was $676, price is now $542 per person
$542
per person
Feb 1 - Feb 7
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Portland (PWM)
7.8/10 Good! (745 reviews)
I would visit again

Reviewed on Dec 4, 2025

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Discover the most popular places to visit in Hillside

Long Beach Marina

5/5(1 review)

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
$109 nightly
The price is $119 total per night from Jan 4 to Jan 5
$119 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
Staff were great. Rooms clean and good breakfast.

Reviewed on Dec 29, 2025

Dormir
Hampton Inn Oxford

Hampton Inn Oxford

2.5 out of 5
151 Main St Oxford ME
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $100 total per night from Jan 11 to Jan 12
$100 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
Everything fine

Reviewed on Dec 26, 2025

Hampton Inn Oxford
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 Jan 4 to Jan 5
$136 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
It was

Reviewed on Dec 29, 2025

Oxford Casino Hotel
See all 1,290 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 $511 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.