Chebeague Island Vacations from $669

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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.
84 Main

84 Main

4 out of 5
Save 100% on your flight
Price was $956, price is now $669 per person
$669
per person
Apr 13 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
10/10 Exceptional! (52 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

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $2,205, price is now $1,513 per person
$1,513
per person
Apr 20 - Apr 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
Went for our honeymoon and fell in love with this place! Will definitely go back!

Reviewed on Feb 26, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $928, price is now $716 per person
$716
per person
May 9 - May 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Portland (PWM)
9.8/10 Exceptional! (86 reviews)
Location is excellent. Short walking distance to every good restaurant and shop. The property was very nice and clean. The kitchen is very well equipped. The gym is very good sized for the size of the apartment building with 13 units in it. The management’s communication was prompt and friendly and responded to all of our wishes. However, the place is advertised as a hotel, but don’t expect services as in a hotel. It resembles more a short term rental home - no cleaning service and no lobby. Otherwise everything was very nice in the apartment and we had a great time.

Reviewed on Jan 3, 2026

The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $1,043, price is now $811 per person
$811
per person
May 9 - May 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
Check-in and check-out are a breeze, easy access to a city parking lot on the block (needed as there was a snow ban on parking when I visited!). In terms of the space itself - clean, well appointed, spacious. Honestly a treat to stay here!

Reviewed on Feb 23, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,134, price is now $891 per person
$891
per person
May 9 - May 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
The whole was cozy! Well curated style and knowledgeable staff.

Reviewed on Jan 5, 2026

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Chebeague Island Hotel Deals

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $108 total per night from Mar 15 to Mar 16
$108 total
Mar 15 - Mar 16
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
Location, clean rooms, pleasant staff

Reviewed on Feb 23, 2026

The Westin Portland Harborview
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $85 total per night from Mar 5 to Mar 6
$85 total
Mar 5 - Mar 6
Total with taxes and fees
8/10 Very Good! (1,384 reviews)
The room was very clean, and the staff was very friendly. The only thing that was disappointing was that when we got ready, and went to use the hot tub it was cold.

Reviewed on Feb 26, 2026

Clarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $173 total per night from Mar 1 to Mar 2
$173 total
Mar 1 - Mar 2
Total with taxes and fees
9.2/10 Wonderful! (1,777 reviews)
Location was great, staff was friendly (especially adam at the front desk) but the bed was very uncomfortable, pillows were cheap and deflated, and the whole "resort fee" was very offputting. I would rather just be told a real rate when I book over getting an extra few hundred in charges. The 35$ ...

Reviewed on Feb 23, 2026

Portland Harbor Hotel
See all 2,194 properties in Chebeague Island
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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Frequently asked questions

How much does a Chebeague Island vacation package cost?
You'll find cheap prices from $669 on Expedia for your Chebeague Island getaway. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Chebeague Island costs.
What are the cheapest months to go to Chebeague Island?
If you'd like to book a cheap Chebeague Island vacation package, consider planning a trip in November, December and January. You'll typically find better prices on hotels and airfares during these months — perfect for budget-conscious travelers.
How many days is enough for Chebeague Island?
With a well-planned schedule, you can easily visit the top Chebeague Island attractions in a few days. But if you prefer to discover hidden spots or go on day trips, consider booking your Chebeague Island vacation for longer.
How to find the best Chebeague Island package deals?
Use Expedia's handy filters to help you find some tempting Chebeague Island package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Chebeague Island package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Chebeague Island vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still get the freedom to create a customized Chebeague Island vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Chebeague Island?
If you have your Chebeague Island travel dates locked in, book as soon as you can to snap up some fantastic deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for setting off on a whim.
Does Expedia offer Book Now, Pay Later Chebeague Island vacation packages?
Jet off on your dream escape to Chebeague Island with our Book Now, Pay Later vacations. There's no need to save up or wait for your next payday — we've joined forces with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to budget for your trip and snap up bargains before they disappear.

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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.