Chebeague Island Vacation Packages

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Your Chebeague Island Vacation

Book a Chebeague Island vacation package that has only the things you need and nothing you don't. Good for festivals, markets and walking, consider staying in the neighborhood of Parkside. If a sightseeing tour is part of the program during your trip to Chebeague Island, check out major attractions like Eagle Island, Little John Island Preserve and Sturdivant Island. That dream Chebeague Island vacation is a couple of clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored to suit your style.

Top Chebeague Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Comfort Inn Airport

Comfort Inn Airport

2.5 out of 5
Price was CA $824, price is now CA $716 per person
CA $716
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.4/10 Very Good! (1,488 reviews)
Bathroom door was very hard to close. Needs repair. Scraped on the floor. Find dinner somewhere before you go if you’re without a car. Bed okay. Would call it a 3-star hotel. Very close to the airport. Convenient van ride to the airport.

Reviewed on Aug. 21, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was CA $1,788, price is now CA $1,328 per person
CA $1,328
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!

Reviewed on Aug. 9, 2025

Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3 out of 5
Downtown Portland
Price was CA $1,351, price is now CA $1,125 per person
CA $1,125
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,003 reviews)
It was great. breakfast was great!

Reviewed on Aug. 18, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Price was CA $1,964, price is now CA $1,662 per person
CA $1,662
per person
Oct 16 - Oct 18
found 11 hours ago
Roundtrip flight included
Québec (YQB) to Portland (PWM)
9.6/10 Exceptional! (219 reviews)
This property was beyond expectation. As long as you are comfortable using the app, check in was super easy and so was getting into our suite. The kitchen had everything we could have possibly needed, and having a living space was a great lift from a normal hotel room.

Reviewed on Aug. 16, 2025

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Downtown Portland
Price was CA $1,822, price is now CA $1,600 per person
CA $1,600
per person
Oct 16 - Oct 18
found 11 hours ago
Roundtrip flight included
Québec (YQB) to Portland (PWM)
8.8/10 Excellent! (1,005 reviews)
Clean hotel. Friendly staff.

Reviewed on Aug. 21, 2025

Ready to book your vacation to Chebeague Island?

 

Choose your dates

Chebeague Island Hotel Deals

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
The price is CA $161 per night from Aug 27 to Aug 28
CA $161
CA $176 total
Aug 27 - Aug 28
includes taxes & fees
7.8/10 Good! (1,214 reviews)
"."

Reviewed on Aug. 21, 2025

Days Inn by Wyndham Airport/Maine Mall
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $211 per night from Aug 27 to Aug 28
CA $211
CA $234 total
Aug 27 - Aug 28
includes taxes & fees
7.8/10 Good! (1,018 reviews)
"The hotel definitely needs a facelift but it was fine for a brief one night stay. The bed was comfortable. When the elevator got stuck on the 5th floor while we waited in the lobby, the front desk clerk was quick to walk up the 5 flights to address the situation."

Reviewed on Aug. 17, 2025

Clarion Hotel Portland
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Sep 2 to Sep 3
CA $176
CA $195 total
Sep 2 - Sep 3
includes taxes & fees
7.8/10 Good! (1,043 reviews)
"The hotel was good enough for the time being (felt safe, clean, etc) but was overall just an okay property."

Reviewed on Aug. 20, 2025

Ramada Plaza by Wyndham Portland
See all 2,280 properties in Chebeague Island
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 Chebeague Island vacation package cost?
You can grab a vacation package to this popular destination from CA $716 on Expedia. However, how much your vacation to Chebeague Island costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Chebeague Island?
To score cheap Chebeague Island vacation packages, organize your trip outside of busy periods like public holidays and major festivals. You'll generally find lower prices and better availability when it's less busy.
How many days is enough for Chebeague Island?
With around 2 days, you'll have enough time to visit popular neighbourhoods like Cousins Island and Town Landing during your Chebeague Island vacation. Be sure to also add Eagle Island and Winslow Memorial Park to your must-see list. In the mood for more adventures? Consider exploring outside of Chebeague Island on tours and day trips.
How to find the best Chebeague Island package deals?
Start your search for a Chebeague Island package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Chebeague Island package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chebeague Island getaway off to a flying start.
Is it cheaper to book a Chebeague Island vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and hotels separately. Better still, you can customize your Chebeague Island trip to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Chebeague Island?
If you have your Chebeague Island travel dates confirmed, book as early as you can to score some awesome deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Chebeague Island?

  1. Pick your travel dates: The things you want to do in Chebeague Island and your favourite season will help you decide when to get away.
  2. Set a budget: Factor in expenses such as flights, transportation and food when working out how much to save for your trip to Chebeague Island. Then, pick a property that matches your budget, whether that's an economical stay or a high-end retreat.
  3. Determine how many days away: Start by listing all the activities and sights you'd like to get to in Chebeague Island. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the right Chebeague Island 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.