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.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Price was CA $1,511, price is now CA $1,168 per person
CA $1,168
per person
Sep 24 - Sep 27
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (196 reviews)
We had a really wonderful visit at the Inn at Diamond Cove. It was a special adventure and the staff tried to work with us to help us enjoy our visit after arriving very late at night for a one night /one day stay. We knew nothing about the inn or the island's history so it was a leap of faith and well worth it.

Reviewed on Jun 29, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $1,790, price is now CA $1,252 per person
CA $1,252
per person
Aug 14 - Aug 17
found 9 hours ago
Roundtrip flight included
Ottawa (YOW) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
Everything was good!

Reviewed on Jul 2, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was CA $3,078, price is now CA $2,529 per person
CA $2,529
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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
Price was CA $2,256, price is now CA $1,874 per person
CA $1,874
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.4/10 Exceptional! (1,771 reviews)
Great room. Excellent location nice courtyard for food and drinks with firepit

Reviewed on Jul 1, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $2,858, price is now CA $2,376 per person
CA $2,376
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.6/10 Exceptional! (185 reviews)
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.

Reviewed on Jun 26, 2026

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Chebeague Island Hotel Deals

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $211 per night from Jul 5 to Jul 6
CA $211
CA $234 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (2,181 reviews)
"Nothing special !"

Reviewed on Jul 2, 2026

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $344 per night from Jul 5 to Jul 6
CA $344
CA $435 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (1,777 reviews)
"Great room. Excellent location nice courtyard for food and drinks with firepit"

Reviewed on Jul 1, 2026

Portland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $353 per night from Jul 5 to Jul 6
CA $353
CA $429 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (1,247 reviews)
"We arrived to the hotel and were greeted by friendly staff. We opted out of the $40 valet parking and found free overnight parking on the street. The rooms were very clean, updated, and spacious. The bed was very comfortable. The location was perfect for getting around. I will definitely be ..."

Reviewed on Jul 2, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,373 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 $1,168 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.