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

La Quinta Inn & Suites by Wyndham Portland
La Quinta Inn & Suites by Wyndham Portland
3 out of 5
340 Park Ave, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$292 per night from 30 June to 1 July
AU$292
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
The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$458 per night from 13 July to 14 July
AU$458
13 July - 14 July
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Super nice and clean. Loved the rooftop bar!"

Reviewed on 20 Jun. 2025

The Westin Portland Harborview
Hyatt Place Portland Downtown - Old Port Square
Hyatt Place Portland Downtown - Old Port Square
3 out of 5
433 Fore St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$388 per night from 30 June to 1 July
AU$388
30 June - 1 July
includes taxes & fees
8.8/10 Excellent! (1,142 reviews)
"Very clean and looks new. New modern style furniture, nice setting and comfortable. New bathroom. Beautiful. Quiet, esp. since this hotel allows pets - no sound to hear from the neighbors. We didn’t hear any barking, meowing or other sounds."

Reviewed on 18 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.