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
Price was CA $1,443, price is now CA $1,031 per person
CA $1,031
per person
Jul 22 - Jul 25
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,003 reviews)
Great experience all around. Will definitely visit again if in the area.
Reviewed on May 25, 2026
The Weldon Hotel
Downtown Portland
Price was CA $2,422, price is now CA $1,927 per person
CA $1,927
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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
Saco Bay Hotel
Price was CA $1,554, price is now CA $1,272 per person
CA $1,272
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
7.6/10 Good! (1,054 reviews)
Rooms were clean. It’s a no frills hotel, but perfectly fine for a one night stop on the way to somewhere else.
Reviewed on May 24, 2026
Portland Harbor Hotel
Downtown Portland
Price was CA $2,293, price is now CA $1,901 per person
CA $1,901
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,774 reviews)
An attractive city hotel with contemporary rooms and a lux feeling lobby area. Ed and pillow were very good; a/c was robust. Downside: The one working elevator to the guest rooms made transit up and downstairs slow.
Reviewed on May 25, 2026
Casco Bay Inn
Price was CA $2,072, price is now CA $1,735 per person
CA $1,735
per person
Aug 9 - Aug 16
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
8/10 Very Good! (1,005 reviews)
No coffee, no keurig, no continental breakfast amenities, and no warning that the place was under massive renovations.
Reviewed on May 18, 2026
Chebeague Island Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
The price is CA $295 per night from May 31 to Jun 1
CA $295
CA $380 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,768 reviews)
"An attractive city hotel with contemporary rooms and a lux feeling lobby area. Ed and pillow were very good; a/c was robust. Downside: The one working elevator to the guest rooms made transit up and downstairs slow."
Reviewed on May 25, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
The price is CA $255 per night from May 28 to May 29
CA $255
CA $282 total
May 28 - May 29
includes taxes & fees
9.4/10 Exceptional! (1,650 reviews)
"Just okay, guest services staff a bit aloof. Can’t beat the location in the heart of the old port. Comfortable bed. Room service closed too early. Nothing in the minibar fridge. Walls are surprisingly thin. I expected more from the Regency."
Reviewed on May 25, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $247 per night from May 31 to Jun 1
CA $247
CA $311 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,220 reviews)
"Updated rooms"
Reviewed on May 26, 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.
