Chebeague Island Vacations from $304
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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.
The Latest Chebeague Island vacation packages
Price found within the past 48 hours. Click for updated prices.
Kennebunkport Captains Collection
Price was $381, price is now $304 per person
$304
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
18.8/10 Exceptional! (649 reviews)
Room was so comfortable and clean. Fireplace was a nice amenity. Great shower. Staff was so friendly and kind. Delicious breakfast. Wonderful location, fantastic stay.
Reviewed on Nov 19, 2025
The Press Hotel, Marriott Autograph Collection
Downtown Portland
Price was $597, price is now $459 per person
$459
per person
Jan 8 - Jan 12
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
18.8/10 Exceptional! (1,000 reviews)
Beautiful hotel, good & convenient restaurant and very short walk to Merrill Auditorium
Reviewed on Nov 6, 2025
AWOL Kennebunkport
Price was $601, price is now $467 per person
$467
per person
Jan 15 - Jan 18
found 11 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
18.8/10 Exceptional! (225 reviews)
Great staff and facilities. Loved the room and the hotel as a whole. Walking distance into the town.
Would highly recommend this place, one of my favourite hotel experiences in recent years.
Reviewed on Nov 4, 2025
Blind Tiger Portland – Carleton Street
West End
Price was $651, price is now $517 per person
$517
per person
Dec 26 - Dec 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
19.2/10 Exceptional! (119 reviews)
Adorable spot in Portland, great location, really cool concept. Felt like an upgraded vacation rental. You don’t have the whole place to yourself but it basically feels like it. Check in and everything was seamless. The local recommendations, games, and snacks were a nice touch. We loved plays scrabble and drinking wine in the parlor. We do wish some items were a bit nicer given the cost. The bathroom could've had nicer facilities (cheap toilet seat, low water pressure) our bed was a rickety. The breakfast delivered was a nice touch but the contents itself kinda fell flat, not as curated as the website made it seem. Overall we still enjoyed our stay and the concept, but the website may have upsold it a bit.
Reviewed on Nov 11, 2025
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Chebeague Island Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $92 total per night from Nov 30 to Dec 1
$92 total
Nov 30 - Dec 1
Total with taxes and fees
7.8/10 Good! (1,231 reviews)
Room was clean.everything worked . Staff was helpful and friendly.
Reviewed on Nov 11, 2025
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $108 total per night from Dec 7 to Dec 8
$108 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Clean room. Staff corrected a booking issue promptly.
Reviewed on Nov 9, 2025
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $157 total per night from Nov 23 to Nov 24
$157 total
Nov 23 - Nov 24
Total with taxes and fees
9.2/10 Wonderful! (1,676 reviews)
Excellent location, helpful front desk, quiet, clean, well-appointed room.
Reviewed on Nov 18, 2025
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.
Find the Best Chebeague Island Vacation Packages
Chebeague Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
Max Temp Winter | 30ºF |
Max Temp Summer | 70ºF |
Top Sights | State Theatre, East End Beach and Portland Museum of Art |
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