Chebeague Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $775 when you book a flight and hotel together*
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    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.
River View Resort

River View Resort

2.5 out of 5
per person
Jul. 13 - Jul. 16
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (256 reviews)
This property was very clean with modern updates. The staff was kind and helpful, pool and hot tub were amazing. Highly recommend River View.

Reviewed on Mar. 11, 2024

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Jul. 13 - Jul. 16
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (900 reviews)
the hotel is very beautiful, I really fell in love with the design and all the hotel's amenities and facilities, I intend to return soon

Reviewed on May 22, 2024

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Aug. 1 - Aug. 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (1,191 reviews)
The hotel was very comfortable and the staff was friendly and helpful.

Reviewed on May 23, 2024

Ramada by Wyndham Saco/Old Orchard Beach Area

Ramada by Wyndham Saco/Old Orchard Beach Area

2.5 out of 5
per person
Aug. 1 - Aug. 8
found 18 hours ago
Roundtrip flight included
Yellowknife (YZF) to Portland (PWM)
6.8/10 (1,000 reviews)
Great experience very friendly

Reviewed on May 16, 2024

Hidden Pond

Hidden Pond

4 out of 5
Save 100% on your flight
per person
Aug. 1 - Aug. 8
found 18 hours ago
Roundtrip flight included
Yellowknife (YZF) to Portland (PWM)
8/10 Very Good! (6 reviews)

Chebeague Island Hotel Deals

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 $313 per night from May 27 to May 28
CA $313
CA $394 total
includes taxes & fees
May 27 - May 28
9/10 Wonderful! (1,194 reviews)
"The hotel was very comfortable and the staff was friendly and helpful."

Reviewed on May 23, 2024

Portland Harbor Hotel
Casco Bay Hotel, Ascend Hotel Collection
Casco Bay Hotel, Ascend Hotel Collection
3.5 out of 5
80 John Roberts Rd., South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Jun. 9 to Jun. 10
CA $121
CA $132 total
includes taxes & fees
Jun 9 - Jun 10
8.6/10 Excellent! (1,495 reviews)
"All good"

Reviewed on May 22, 2024

Casco Bay Hotel, Ascend Hotel Collection
Canopy by Hilton Portland Waterfront
Canopy by Hilton Portland Waterfront
4 out of 5
9 Center Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $313 per night from May 27 to May 28
CA $313
CA $346 total
includes taxes & fees
May 27 - May 28
9.2/10 Wonderful! (648 reviews)
"Great hotel in a good location along the waterfront. The rooms were lovely, and the rooftop bar is great."

Reviewed on May 21, 2024

Canopy by Hilton Portland Waterfront
See all 2,069 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

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chebeague Island vacation package cost?
Less than you might think — from only CA $694, actually! By bundling flights, hotels and car rentals into your own tailor-made package, your trip to Chebeague Island is only clicks away.
How do I get a cheap travel package to Chebeague Island?
Secure flights that fit your schedule, add a hotel room to your booking and watch the savings stack up with a Chebeague Island vacation package. It’s as easy as that! From hotels and flights to rental cars and tours, Expedia makes traveling on the cheap easy. And with more than 550 air carriers and 1,000,000 hotels around the globe to choose from, you won’t be short of choice.
How far in advance should I book my Chebeague Island vacation?
Savvy travelers will likely want to book as early as possible. You can usually look up international fares on Expedia up to 12 months before your flight. If you’ve left things to the last minute, don’t despair. Cheap prices sometimes occur just weeks prior to departure.
What does an Expedia Chebeague Island travel package include?
From hotels and airfares to car rentals, Expedia can help you create a Chebeague Island package that fits you. Heading away for a while? Give some thought to a flight, rental car and hotel bundle. If you’re taking a quick break, a hotel and flight deal could suit you better. Experiences can also be added once you’ve made your booking. Our vacation packages make it a breeze to plan and save.
What should I know before booking a Chebeague Island travel package?
When you book your hotels, flights and car rentals together, you’ll pick up fantastic discounts. Whether you’re planning a beach escape in a villa or want to stay in a ritzy city hotel, Expedia can help make it happen.
Can I choose my airline with a Chebeague Island Expedia vacation package?
You can. Expedia has access to more than 550 partner airlines globally, so fly with the carrier that best fits your travel needs.
If I'm not able to travel, can I cancel my Chebeague Island vacation package?
Don’t stress if you’re rethinking your Chebeague Island vacation package — you can cancel or amend your booking. And if you’ve booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We know life can occasionally throw a spanner in the travel works, so make your way to our Customer Service Portal if that happens. When you’re ready to make changes, we’ll be here to help.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.