Chebeague Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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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.
The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
per person
Sep 22 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (25 reviews)
Excellent and highly recommend!

Reviewed on Jun. 27, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Aug 21 - Aug 25
found 2 hours ago
Roundtrip flight included
Halifax (YHZ) to Portland (PWM)
9.2/10 Wonderful! (1,533 reviews)
Lovely hotel in a perfect location - some elements of the room hadn’t been cleaned that well but made up for by the complimentary coffee and cookie station.

Reviewed on Jul. 3, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
per person
Sep 22 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (209 reviews)
Great place! Super convenient

Reviewed on Jul. 4, 2025

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
per person
Aug 21 - Aug 25
found 2 hours ago
Roundtrip flight included
Halifax (YHZ) to Portland (PWM)
9.4/10 Exceptional! (1,318 reviews)
Absolutely lovely and convenient hotel. Only complaint was about the air conditioning. Even though it wasn’t that hot a night (in the 60s) and day (80). The cooling struggled to keep up. We wanted the temperature to be 68 but we couldn’t get it cooler than 73.

Reviewed on Jul. 5, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
per person
Aug 21 - Aug 25
found 2 hours ago
Roundtrip flight included
Halifax (YHZ) to Portland (PWM)
9.6/10 Exceptional! (147 reviews)
Everything was wonderful, we highly recommend staying here to anyone considering it.

Reviewed on Jun. 13, 2025

Ready to book your vacation to Chebeague Island?

 

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Chebeague Island Hotel Deals

Chebeague Island Inn
Chebeague Island Inn
4 out of 5
61 South Road, Chebeague Island, ME
The price is CA $407 per night from Jul 7 to Jul 8
CA $407
CA $537 total
Jul 7 - Jul 8
includes taxes & fees
8.6/10 Excellent! (72 reviews)
Nice place but rooms could use a major update
"2 nights as a couple while the kids are away. The location and hotel surroundings are nice, but the rooms are old and not well maintained. There is however a great porch with ocean views"

Reviewed on Jul. 4, 2025

Chebeague Island Inn
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 $207 per night from Jul 8 to Jul 9
CA $207
CA $229 total
Jul 8 - Jul 9
includes taxes & fees
7.8/10 Good! (1,005 reviews)
"Everything is good. Coffee and tea in lobby ."

Reviewed on Jul. 5, 2025

Clarion Hotel Portland
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
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Jul 7 to Jul 8
CA $158
CA $172 total
Jul 7 - Jul 8
includes taxes & fees
7.8/10 Good! (1,007 reviews)
"Perfect"

Reviewed on Jul. 4, 2025

Days Inn by Wyndham Airport/Maine Mall
See all 2,347 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.

All Inclusive Vacations

All Inclusive Vacations

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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 $1,093 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.