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.
84 Main
Price was CA $1,391, price is now CA $1,171 per person
CA $1,171
per person
May 2 - May 5
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Portland (PWM)
9.8/10 Exceptional! (56 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.
Reviewed on Dec 29, 2025
Kennebunkport Captains Collection
Price was CA $1,446, price is now CA $1,255 per person
CA $1,255
per person
May 26 - May 29
found 11 hours ago
Roundtrip flight included
Edmonton (YEG) to Portland (PWM)
9.4/10 Exceptional! (686 reviews)
Historic, cozy, and charming mansions and rooms...our stay was amazing.
Reviewed on Mar 15, 2026
Blind Tiger Portland – Carleton Street
West End
Price was CA $2,180, price is now CA $1,903 per person
CA $1,903
per person
May 16 - May 21
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (121 reviews)
Given there's no staff onsite, questions and communication are all remote, leading to delay in response. Rooms were cold and heating was hard to adjust.
Reviewed on Mar 6, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was CA $1,988, price is now CA $1,739 per person
CA $1,739
per person
May 2 - May 5
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Portland (PWM)
9.6/10 Exceptional! (175 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!
Reviewed on Mar 10, 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 $135 per night from Apr 13 to Apr 14
CA $135
CA $149 total
Apr 13 - Apr 14
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
The staff was very helpful. Breakfast was included. Full service, not continental. Really good food. Parking was validated. No surprises on put bill. Definitely recommended.
Reviewed on Mar 22, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
The price is CA $106 per night from Apr 13 to Apr 14
CA $106
CA $117 total
Apr 13 - Apr 14
includes taxes & fees
8/10 Very Good! (1,404 reviews)
Clean room , nice pool area and quiet ,will say that the beds are kinda uncomfortable but if you’re there for a night it’s not too bad ! I’d come back again.
Reviewed on Mar 22, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,773 reviews)
A very nice and unique hotel in a great location. Would definitely stay again.
Reviewed on Mar 21, 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.
