Chebeague Island Vacations from $419

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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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $722, price is now $419 per person
$419
per person
Jan 7 - Jan 13
found 1 hour ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (1,621 reviews)
Clean room, friendly staff, nice accommodations and centrally located to the downtown restaurants!

Reviewed on Oct 21, 2025

The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
Price was $888, price is now $542 per person
$542
per person
Jan 7 - Jan 13
found 1 hour ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (69 reviews)
Picturesque and quiet location! Laundry facilities! Staff was more than accommodating and a lovely ocean view with a delicious breakfast made for a memorable stay!

Reviewed on Oct 21, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,753, price is now $1,151 per person
$1,151
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
9.4/10 Exceptional! (1,016 reviews)
Absoltely incredible views- the cliffs were the perfect place to catch the sunrise. The restaurant was wonderful and the staff were super friendly and helpful. Extremely comfortable room and the hot tub and indoor pool were fantastic.

Reviewed on Oct 20, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $920, price is now $647 per person
$647
per person
Jan 7 - Jan 13
found 1 hour ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.6/10 Exceptional! (239 reviews)
Beautiful space. We will be back.

Reviewed on Oct 21, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $1,058, price is now $765 per person
$765
per person
Jan 7 - Jan 13
found 1 hour ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.6/10 Exceptional! (155 reviews)
Beautiful historic building. The common areas and our room were stunning! Breakfast in the morning was great. Make sure to go to the widow’s walk in the evening for a view.

Reviewed on Oct 16, 2025

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Chebeague Island Hotel Deals

Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $92 total per night from Nov 11 to Nov 12
$92 total
Nov 11 - Nov 12
Total with taxes and fees
7.8/10 Good! (1,168 reviews)
"The free shuttle was right on time. We stayed here to catch a super early bus to NYC. We have stayed here before. The staff is friendly. The room is very comfortable and it's a great place to stay when you're catching a bus."

Reviewed on Oct 20, 2025

Clarion Hotel Portland
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
$170 nightly
The price is $188 total per night from Nov 16 to Nov 17
$188 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (1,632 reviews)
"It was a very nice and comfortable hotel. Walkable to everything. I would stay here agaiin."

Reviewed on Oct 19, 2025

Portland Harbor Hotel
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $103 total per night from Oct 26 to Oct 27
$103 total
Oct 26 - Oct 27
Total with taxes and fees
7.8/10 Good! (1,035 reviews)
"Clean room. Friendly staff."

Reviewed on Oct 20, 2025

Fireside Inn & Suites Portland
See all 2,245 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 $419 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.