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.
River View Resort
Price was CA $1,655, price is now CA $1,119 per person
CA $1,119
per person
Jun 28 - Jul 4
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (323 reviews)
Clean room. Space for everyone, pool was nice, staff was friendly. Perfect for our last minute ski trip.
Reviewed on Apr 12, 2026
Kennebunkport Captains Collection
Price was CA $2,888, price is now CA $2,140 per person
CA $2,140
per person
Jun 28 - Jul 4
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (692 reviews)
Historic, cozy, and charming mansions and rooms...our stay was amazing.
Reviewed on Mar 15, 2026
Port Inn & Suites Kennebunk, an Ascend Collection Hotel
Price was CA $1,662, price is now CA $1,332 per person
CA $1,332
per person
Jun 28 - Jul 4
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (1,003 reviews)
Was a bad continental breakfast as cheap as you can get, bedding was thin and bed not that comfortable. Shower was meh. Staff was very nice and still a cute cozy place to stay. Very simple
Reviewed on Apr 17, 2026
Chebeague Island Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Apr 23 to Apr 24
CA $203
CA $225 total
Apr 23 - Apr 24
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Desk staff was very friendly and helpful, and we were pleasantly surprised to get a corner room with stunning views. Will definitely be back!
Reviewed on Apr 21, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
The price is CA $166 per night from Apr 26 to Apr 27
CA $166
CA $236 total
Apr 26 - Apr 27
includes taxes & fees
9.2/10 Wonderful! (1,760 reviews)
Close to Becky’s Diner !
Reviewed on Apr 19, 2026
HomeAwhile
205 Southborough Drive Scarborough ME
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Apr 23 to Apr 24
CA $162
CA $177 total
Apr 23 - Apr 24
includes taxes & fees
9.6/10 Exceptional! (24 reviews)
Super nice place!!
Reviewed on Apr 19, 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.
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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.
