Chebeague Island Vacations from $328

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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.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
Price was $410, price is now $328 per person
$328
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
7.8/10 Good! (1,052 reviews)
Property is good . Nice area and convenient

Reviewed on Aug 22, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,741, price is now $1,147 per person
$1,147
per person
Oct 3 - Oct 6
found 3 hours ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!

Reviewed on Aug 9, 2025

The McKernan Inn

The McKernan Inn

3 out of 5
Price was $706, price is now $537 per person
$537
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9/10 Wonderful! (47 reviews)
Quiet and peaceful with views of the Bay. Easy to access and close to downtown Portland

Reviewed on Aug 18, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Price was $1,569, price is now $1,274 per person
$1,274
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
9.6/10 Exceptional! (226 reviews)
I had a wonderful stay! The place was clean, cozy, and exactly as described. The location was perfect, which made everything smooth and easy. I’d happily stay here again and recommend it to anyone visiting Portland.

Reviewed on Aug 22, 2025

Microtel Inn & Suites by Wyndham York

Microtel Inn & Suites by Wyndham York

2 out of 5
Price was $848, price is now $699 per person
$699
per person
Sep 26 - Oct 3
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
8/10 Very Good! (1,000 reviews)
Staff were very attentive. Breakfast was well done. Pool was great. Location was excellent.

Reviewed on Aug 14, 2025

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Chebeague Island Hotel Deals

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $127 total per night from Aug 24 to Aug 25
$127 total
Aug 24 - Aug 25
Total with taxes and fees
7.8/10 Good! (1,223 reviews)
Excellent choice for single night stay
"Very convenient hotel for those flying into PWM. Quick stop on the way to Rockland. Front desk was pleasant. Got me toothpaste I forgot. Told them about stopped up sink and they noted it. (It wasn't an issue for me as I simply removed the stopper and left it on the counter to be cleaned.) Breakfast ..."

Reviewed on Aug 22, 2025

Days Inn by Wyndham Airport/Maine Mall
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $168 total per night from Aug 26 to Aug 27
$168 total
Aug 26 - Aug 27
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
"I like the room and accommodations. The front desk person was a bit brief with me though."

Reviewed on Aug 22, 2025

Clarion Hotel Portland
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $141 total per night from Sep 2 to Sep 3
$141 total
Sep 2 - Sep 3
Total with taxes and fees
7.8/10 Good! (1,043 reviews)
"The hotel was good enough for the time being (felt safe, clean, etc) but was overall just an okay property."

Reviewed on Aug 20, 2025

Ramada Plaza by Wyndham Portland
See all 2,280 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.

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Frequently asked questions

How much does a Chebeague Island vacation package cost?
You'll find cheap prices from $328 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.