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.
The Latest Chebeague Island Vacation Packages
- Portland Regency Hotel & Spa
Dec 29 - Jan 3Portland Regency Hotel & Spa + Flight
Downtown Portland5 nights3.5 star property9.4/10 - Exceptional (1,815 reviews)"Clean room"Reviewed November 8, 2026Roundtrip • Ottawa (YOW) - Portland (PWM)YOW - PWM • 1 stop PWM - YOW • 1 stopCA $1,929CA $1,713found 1 day agoper traveller - Blind Tiger Portland - Danforth Street.
Dec 29 - Jan 3Blind Tiger Portland - Danforth Street. + Flight
West End5 nights3.5 star property9.6/10 - Exceptional (206 reviews)Roundtrip • Ottawa (YOW) - Portland (PWM)YOW - PWM • 1 stop PWM - YOW • 1 stopCA $3,861CA $3,084found 1 day agoper traveller - Inn By The Sea
Dec 29 - Jan 3Inn By The Sea + Flight
Cape Elizabeth5 nights4.0 star property9.6/10 - Exceptional (346 reviews)Roundtrip • Ottawa (YOW) - Portland (PWM)YOW - PWM • 1 stop PWM - YOW • 1 stopCA $2,421CA $2,074found 1 day agoper traveller - The Docent's Collection at 121 Middle Street
Dec 29 - Jan 3The Docent's Collection at 121 Middle Street + Flight
Downtown Portland5 nights3.5 star property9.6/10 - Exceptional (429 reviews)"Pros: Room was nice and spacious. Kitchen had everything we needed. Location was awesome - very close to all the things we wanted to do. Excellent proximity to some of the best restaurants, including LB Kitchen, Fore Street, Central Provisions. Con’s: Couches could have benefited from some throw pillows - kinda weird without any. Bed wasn’t that comfortable - you sink in way too much. Parking was ok - just some weird communication before our arrival about where to park. Text messages from the..."Reviewed November 8, 2026Roundtrip • Ottawa (YOW) - Portland (PWM)YOW - PWM • 1 stop PWM - YOW • 1 stopCA $2,498CA $2,166found 1 day agoper traveller - Evalina Hotel
Dec 29 - Jan 3Evalina Hotel + Flight
Downtown Portland5 nights2.5 star property10/10 - Exceptional (19 reviews)Roundtrip • Ottawa (YOW) - Portland (PWM)YOW - PWM • 1 stop PWM - YOW • 1 stopCA $3,483CA $3,081found 1 day agoper traveller
Chebeague Island Hotel Deals
Holiday Inn Express Hotel & Suites Freeport by IHG
Holiday Inn Express Hotel & Suites Freeport by IHG"Nice place and very friendly people"
"This place was a real find. The price was very reasonable. The staff was great and the amenities were more than I expected for the price. I found the room very comfortable and clean and I enjoyed the free breakfast. I would highly recommend this place."
Hampton Inn Freeport/Brunswick
Hampton Inn Freeport/Brunswick
SpringHill Suites by Marriott Freeport Brunswick
SpringHill Suites by Marriott Freeport Brunswick"Great hotel!"
The Freeport Hotel, an Ascend Collection Hotel
The Freeport Hotel, an Ascend Collection Hotel"Pay extra to stay somewhere else"
Hilton Garden Inn Freeport Downtown
Hilton Garden Inn Freeport Downtown"Needs to widen their menu at the bar"
"Amazing view! Quiet, quaint and perfect"
Frequently Asked Questions
How much does a Chebeague Island vacation package cost?
You can grab a vacation package to this popular destination from CA $1,713 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?
- 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.
- 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.
- 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.
- 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.