Chebeague Island Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Ogunquit River Inn & Suites
Moody
Price was CA $2,048, price is now CA $1,532 per person
CA $1,532
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,005 reviews)
No curb appeal from the road at all...yet..once behind property..everything changes!.Great bed..better pillows!
None of the bedside lights or plugs were functioning...and upon entering room...no air conditioning on...and the room was over 90 degrees...took over 2 hours for it to cool down..
Views are superb...pool was relaxing!
Reviewed on Jun 11, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was CA $4,545, price is now CA $3,300 per person
CA $3,300
per person
Jul 19 - Jul 24
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.6/10 Exceptional! (184 reviews)
Looks better on photos than in real life. Basically a nice B&B with dated amenities and utilities. Also a bit out of the way. But its charming.
Reviewed on Jun 12, 2026
Portland Regency Hotel & Spa
Downtown Portland
Price was CA $2,437, price is now CA $1,872 per person
CA $1,872
per person
Jul 19 - Jul 24
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (1,679 reviews)
We loved the hotel. The location is great and convenient to the best parts of Portland. The room was perfect with a comfortable bed a great bathroom. Staff was friendly and helpful. We would happily stay again at your hotel.
Reviewed on Jun 13, 2026
Portland Harbor Hotel
Downtown Portland
Price was CA $2,254, price is now CA $1,825 per person
CA $1,825
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,781 reviews)
We had a great stay! Everyone was so nice, helpful, and efficient! We loved the location. Portland is an amazing city! Wasn’t aware of the $35 a day charges but it worked out!
Reviewed on Jun 12, 2026
The Francis
Parkside
Price was CA $3,277, price is now CA $2,671 per person
CA $2,671
per person
Jul 19 - Jul 24
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (391 reviews)
Great location, comfortable bed, charming property, friendly and helpful staff.
Reviewed on May 1, 2026
Chebeague Island Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
The price is CA $194 per night from Jun 16 to Jun 17
CA $194
CA $215 total
Jun 16 - Jun 17
includes taxes & fees
8/10 Very Good! (1,496 reviews)
"One elevator was out of order. The other elevator did not stop at my floor. Carpet is threadbare. There were stains in the sink and tub."
Reviewed on Jun 13, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $395 per night from Jul 5 to Jul 6
CA $395
CA $491 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (1,785 reviews)
"We had a great stay! Everyone was so nice, helpful, and efficient! We loved the location. Portland is an amazing city! Wasn’t aware of the $35 a day charges but it worked out!"
Reviewed on Jun 12, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $389 per night from Jun 21 to Jun 22
CA $389
CA $468 total
Jun 21 - Jun 22
includes taxes & fees
9.4/10 Exceptional! (1,250 reviews)
"Great area, very walkable, the staff was excellent! Would definitely stay again."
Reviewed on Jun 13, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
