Hillside Vacations from $919

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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.
Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
Save 100% on your flight
Price was $1,362, price is now $919 per person
$919
per person
Aug 2 - Aug 7
found 1 hour ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (341 reviews)
IT WAS CHARMING AND BEAUTIFUL. The restaurant was wonderful, all the staff was first class, would love to go back.

Reviewed on Oct 14, 2025

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
Price was $1,578, price is now $951 per person
$951
per person
Aug 2 - Aug 7
found 1 hour ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9/10 Wonderful! (1,003 reviews)
Very convenient and helpful staff.

Reviewed on May 10, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,973, price is now $1,219 per person
$1,219
per person
Jul 15 - Jul 20
just found
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
8.6/10 Excellent! (1,001 reviews)
Very well kept… great staff we had a great time

Reviewed on Apr 14, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,354, price is now $1,597 per person
$1,597
per person
Jul 5 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Lovely suite! Comfy king bed, everything spotless, Great location. Would stay here again

Reviewed on Apr 23, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,929, price is now $1,345 per person
$1,345
per person
Jul 5 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (1,753 reviews)
Best location in Portland. The free bikes were the highlight, We went everywhere with them. Very convenient! The staff was very nice.

Reviewed on May 10, 2026

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Discover the most popular places to visit in Hillside

Red boat

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
$154 nightly
The price is $167 total per night from May 12 to May 13
$167 total
May 12 - May 13
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
Dormir in Windham was perfect for my needs. The front desk agent who checked me in at 2:00 a.m. was friendly and helpful. The hotel reception area and my room were spotlessly clean. My room had a really nice configuration: one large bed (much better than the typical 2 queens for a single guest!), ...

Reviewed on May 10, 2026

Dormir
Oxford Casino Hotel

Oxford Casino Hotel

3 out of 5
777 Casino Way Oxford ME
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $123 total per night from May 20 to May 21
$123 total
May 20 - May 21
Total with taxes and fees
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
$98 nightly
The price is $107 total per night from May 18 to May 19
$107 total
May 18 - May 19
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
Our stay was pleasant. Staff was helpful. Breakfast was one of the best of all the places we've been.

Reviewed on Apr 26, 2026

Hampton Inn Oxford
See all 1,336 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 $919 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.