Chebeague Island Holidays

    deals illustration

    Better together

    Save up to €185 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Chebeague Island

Chebeague Island Inn
Chebeague Island Inn
4 out of 5
61 South Road, Chebeague Island, ME
8.6/10 Excellent! (72 reviews)
Nice place but rooms could use a major update
"2 nights as a couple while the kids are away. The location and hotel surroundings are nice, but the rooms are old and not well maintained. There is however a great porch with ocean views"

Reviewed on 4 Jul 2025

Get rates
Chebeague Island Inn
Clarion Hotel Portland
Clarion Hotel Portland
2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is €144 per night from 13 Jul to 14 Jul
€144
13 Jul - 14 Jul
includes taxes & fees
7.8/10 Good! (1,013 reviews)
"Nice hotel close to the airport with shuttle service"

Reviewed on 7 Jul 2025

Clarion Hotel Portland
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
The price is €120 per night from 13 Jul to 14 Jul
€120
13 Jul - 14 Jul
includes taxes & fees
7.8/10 Good! (1,024 reviews)
Great hotel, right across from the mall and close
"I stayed at this hotel with a number of years ago and then it was closed for a few years I think or repurposed. They have redone the place and it really looks nice. It’s clean and friendly. Breakfast was delicious. I will stay here again soon."

Reviewed on 6 Jul 2025

Days Inn by Wyndham Airport/Maine Mall
See all 2,345 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.

Frequently asked questions

How much does a Chebeague Island holiday package cost?
You'll find cheap prices 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 holiday to Chebeague Island costs.
What are the cheapest months to go to Chebeague Island?
The off-season is the best time to visit Chebeague Island if you're trying to save. Another tip for finding cheap Chebeague Island holiday packages? Try to avoid visiting during public holidays and any major events or festivals.
How many days is enough for Chebeague Island?
Generally, a handful of days is enough to go to the main attractions during your Chebeague Island holiday. But if you'd like to have some time to kick back or go on day trips, consider extending your trip.
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 holiday package as soon as possible.
Is it cheaper to book a Chebeague Island holiday as a package?
Expedia holiday 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 customised Chebeague Island holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday 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.
How to plan a trip to Chebeague Island?

  1. Choose when to go: Check your calendar and get packing. Your preferred time of year and the type of activities available will also help you decide when to holiday in Chebeague Island.
  2. Budget wisely: In addition to the cost of your hotel, you'll need to factor in other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Chebeague Island.
  3. Decide your trip length: Consider how long you want to spend discovering Chebeague Island. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to pick a Chebeague Island holiday package that brings all your bookings together.