Chebeague Island Holidays

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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

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Chebeague Island Inn
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 S$194 per night from 14 Jul to 15 Jul
S$194
14 Jul - 15 Jul
includes taxes & fees
7.8/10 Good! (1,017 reviews)
"This property was a pleasure to stay at when I couldn’t get a hotel at Old Orchard Beach. Fernando at the front desk made everything so much better at check-in and also when I wanted to extend my stay. He really is the best, right along with the rest of the staff. The amenities were great as well ..."

Reviewed on 11 Jul, 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
The price is S$216 per night from 20 Jul to 21 Jul
S$216
20 Jul - 21 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
See all 2,348 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.