Hillside Vacations from $968

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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.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,440, price is now $968 per person
$968
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Had a great stay. Kind and helpful staff. Will be back!

Reviewed on Jul 11, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,885, price is now $1,270 per person
$1,270
per person
Sep 21 - Sep 25
found 16 hours ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
10/10 Exceptional! (5 reviews)
It was a spacious, clean, well thought out space with all the expected amenities. The location is ideal, and the hotel is truly a treasure.

Reviewed on Jun 28, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,561, price is now $1,083 per person
$1,083
per person
Sep 21 - Sep 25
found 16 hours ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Spacious with plenty of room for my family of four. Excellent kitchen, washer and dryer and stellar location close to Waterfront district.

Reviewed on Jul 5, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $2,289, price is now $1,675 per person
$1,675
per person
Sep 21 - Sep 25
found 16 hours ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
9.6/10 Exceptional! (188 reviews)
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.

Reviewed on Jun 26, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,371, price is now $1,021 per person
$1,021
per person
Aug 26 - Aug 30
found 16 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (1,682 reviews)
Some amenities were not available at the time of my stay.

Reviewed on Jul 11, 2026

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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.
See properties

Hillside Hotel Deals

Oxford Casino Hotel

Oxford Casino Hotel

3 out of 5
777 Casino Way Oxford ME
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $133 total per night from Aug 10 to Aug 11
$133 total
Aug 10 - Aug 11
Total with taxes and fees
8.6/10 Excellent! (1,010 reviews)
"n"

Reviewed on Jul 11, 2026

Oxford Casino Hotel
Dormir

Dormir

3 out of 5
965 Roosevelt Trail Windham ME
Fully refundableReserve now, pay when you stay
$231 nightly
The price is $252 total per night from Jul 22 to Jul 23
$252 total
Jul 22 - Jul 23
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
"The property was clean and well maintained. The room was also clean and organized. I would recommend this property if you’re looking for a comfortable bed and a clean property."

Reviewed on Jul 7, 2026

Dormir
Hampton Inn Oxford

Hampton Inn Oxford

2.5 out of 5
151 Main St Oxford ME
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $124 total per night from Jul 20 to Jul 21
$124 total
Jul 20 - Jul 21
Total with taxes and fees
9/10 Wonderful! (1,010 reviews)
"Good breakfast, nice rooms. Site was a bit noisy, even near McCarran airport. We arrived"

Reviewed on Jul 12, 2026

Hampton Inn Oxford
See all 1,388 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 $968 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.