Chebeague Island Holidays

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Your Chebeague Island Holiday

An easy way to experience this exciting city is with a custom-made Chebeague Island holiday package. Stay in the neighbourhood of Parkside, which is good for festivals, markets and walking or go someplace else — our packages are all about you. Make your trip to Chebeague Island even more fun by going sightseeing. Wolfes Neck Woods State Park, Bailey Island Bridge and Little John Island Preserve are among the major attractions you'll want to explore. No matter your travel plans or the size of your budget, organising a tailored Chebeague Island holiday is a piece of cake with Expedia.

Chebeague Island Holiday

Chebeague Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Max Temp Winter
-1.11ºC
Max Temp Summer
21ºC
Top Sights
State Theatre, Portland Museum of Art and East End Beach

Our pick of the best Chebeague Island Hotel Deals

Chebeague Island Inn
Chebeague Island Inn
4 out of 5
61 South Road, Chebeague Island, ME
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (70 reviews)
"The location is perfect with the golf course right next door and sitting up on the hill overlooking the harbor. The restaurant serves wonderful meals, one of the best lobster bisque we’ve ever had. The wrap around porch is awesome with heaters. In saying all this, the inn needs some TLC. Our room ..."

Reviewed on 20 Jun. 2025

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Chebeague Island Inn
La Quinta Inn & Suites by Wyndham Portland
La Quinta Inn & Suites by Wyndham Portland
3 out of 5
340 Park Ave, Portland, ME
The price is AU$291 per night from 30 June to 1 July
AU$291
30 June - 1 July
includes taxes & fees
8.8/10 Excellent! (2,172 reviews)
"No surprises"

Reviewed on 18 Jun. 2025

La Quinta Inn & Suites by Wyndham Portland
Hyatt Place Portland Downtown - Old Port Square
Hyatt Place Portland Downtown - Old Port Square
3 out of 5
433 Fore St, Portland, ME
The price is AU$436 per night from 30 June to 1 July
AU$436
30 June - 1 July
includes taxes & fees
8.8/10 Excellent! (1,145 reviews)
"The location is perfect for a day in the city. Close to everything. The staff was friendly. The free shuttle to the airport was easy to arrange with the service offered 24 hours. I was transported at 3:20 am to the airport saving the cost of an Uber and assured safety at the hour. The gym was under ..."

Reviewed on 23 Jun. 2025

Hyatt Place Portland Downtown - Old Port Square
See all 2,318 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

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.