Chebeague Island Vacations from $841
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The Latest Chebeague Island Vacation Packages
- Ogunquit River Inn & Suites
Oct 19 - Oct 24Ogunquit River Inn & Suites + Flight
Moody5 nights3.0 star property9.0/10 - Wonderful (1,010 reviews)"The overall property was good. There were some definite problems with the handicap room we requested. 1. There was no where to hang clothes. 2. I had to request a luggage stand or use the floor for my bag. 3. The shower was walk in but the shower head was not hand held. 4. Definitely not an ADA approved room."Reviewed August 1, 2026Roundtrip • Atlanta (ATL) - Portland (PWM)ATL - PWM • Nonstop PWM - ATL • Nonstop$1,168$841found 1 day agoper traveler - Evalina Hotel
Oct 19 - Oct 24Evalina Hotel + Flight
Downtown Portland5 nights2.5 star property10/10 - Exceptional (7 reviews)"The accommodations were perfect for a family of 4. The 2 bedroom/2 bath was very spacious, very well laid out and in an excellent location. We really enjoyed our stay!"Reviewed July 28, 2026Roundtrip • Atlanta (ATL) - Portland (PWM)ATL - PWM • Nonstop PWM - ATL • Nonstop - The Meadowmere Resort
Oct 2 - Oct 8The Meadowmere Resort + Flight
Ogunquit6 nights2.5 star property8.6/10 - Excellent (1,005 reviews)"Was a nice place to stay. Would stay there again."Reviewed July 31, 2026Roundtrip • Atlanta (ATL) - Portland (PWM)ATL - BOS • Nonstop BOS - ATL • Nonstop - Blind Tiger Portland - Danforth Street.
Oct 19 - Oct 24Blind Tiger Portland - Danforth Street. + Flight
West End5 nights3.5 star property9.6/10 - Exceptional (189 reviews)"This hotel is amazing. The rooms, beds, and all the details are so incredible. I wish I could have stayed longer. Check in was a breeze as well. You can tell they take a lot of care and thought into the property. I will definitely be back"Reviewed July 25, 2026Roundtrip • Atlanta (ATL) - Portland (PWM)ATL - PWM • Nonstop PWM - ATL • Nonstop - Blind Tiger Portland – Carleton Street
Oct 19 - Oct 24Blind Tiger Portland – Carleton Street + Flight
West End5 nights3.5 star property9.6/10 - Exceptional (128 reviews)Roundtrip • Atlanta (ATL) - Portland (PWM)ATL - PWM • Nonstop PWM - ATL • Nonstop
Chebeague Island Hotel Deals
Holiday Inn Express Hotel & Suites Freeport by IHG
Holiday Inn Express Hotel & Suites Freeport by IHG
The Freeport Hotel, an Ascend Collection Hotel
The Freeport Hotel, an Ascend Collection Hotel
Econo Lodge Freeport - Brunswick Area
Econo Lodge Freeport - Brunswick Area
SpringHill Suites by Marriott Freeport Brunswick
SpringHill Suites by Marriott Freeport Brunswick
Frequently Asked Questions
How much does a Chebeague Island vacation package cost?
You'll find cheap prices from $841 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.