Hillside Vacation Packages

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Top Hillside Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (177 reviews)
We had an amazing stay! What a gem of an experience - all of the staff was wonderful - Antonio at the lobby cafe was so kind and friendly and Kayla at concierge always went above and beyond!!

Reviewed on Jul. 20, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,008 reviews)
The oceanview was breathtaking, the morning sun was stunning

Reviewed on Jul. 22, 2025

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,338 reviews)
Charming and very welcoming staff. We were able to walk everywhere easily. Great location!

Reviewed on Jul. 23, 2025

Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
Downtown Portland
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Portland (PWM)
8.8/10 Excellent! (1,153 reviews)
Great location and wonderful customer service! Really quiet in the room so you can hear quite a bit outside, shower pressure wasn't great but bed was comfortable and room was clean. There was some construction going on that we weren't aware of but it wasn't a deal breaker. Love that they offer airport shuttle!

Reviewed on Jul. 22, 2025

Chebeague Island Inn

Chebeague Island Inn

4 out of 5
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (72 reviews)
Great place to go and relax for a few days.

Reviewed on Jul. 20, 2025

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Hillside Hotel Deals

Dormir

Dormir

3 out of 5
965 Roosevelt Trail, Windham, ME
Fully refundableReserve now, pay when you stay
The price is CA $316 per night from Jul 28 to Jul 29
CA $316
CA $345 total
Jul 28 - Jul 29
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"I liked it! Thanks for a good stay"

Reviewed on Jul. 20, 2025

Dormir
Oxford Casino Hotel

Oxford Casino Hotel

3 out of 5
777 Casino Way, Oxford, ME
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Jul 28 to Jul 29
CA $171
CA $187 total
Jul 28 - Jul 29
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"The property is nice. The room was huge and clean. We arrived early and I asked the lady at the desk about an early check in. We checked in on a Monday so I thought we might be able to get in early. She informed us that if we wanted earlier check in we would have to pay an extra $30 plus tax. I’ve ..."

Reviewed on Jul. 20, 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
The price is CA $208 per night from Jul 28 to Jul 29
CA $208
CA $226 total
Jul 28 - Jul 29
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"This was the fourth year in a row to stay at the Hampton Inn Oxford on my vacation. The staff is always very friendly and helpful and the room is very clean and spacious. The free breakfast is great with many different choices. Most importantly the Oxford casino is right across the street. I will ..."

Reviewed on Jul. 17, 2025

Hampton Inn Oxford
See all 1,356 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.
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Frequently asked questions

How much does a Hillside vacation package cost?
Offering great value package deals from CA $858 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.