Chebeague Island Holidays

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    Packages with flights are ATOL protected

Your Chebeague Island Holiday

Book a Chebeague Island holiday package that has only the things you need and nothing you don't. Good for festivals, markets and walking, consider staying in the neighbourhood of Parkside. If a sightseeing tour is part of the programme during your trip to Chebeague Island, check out major attractions like Eagle Island, Little John Island Preserve and Sturdivant Island. That dream Chebeague Island holiday is a couple of clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored to suit your style.

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, East End Beach and Portland Museum of Art

Top hotels in Chebeague Island

Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
Fully refundable
The price is £75 per night from 6 Sept to 7 Sept
£75
6 Sept - 7 Sept
includes taxes & fees
7.4/10 Good! (639 reviews)
"Piscine et déjeuner"

Reviewed on 5 Aug 2026

Clarion Pointe South Portland
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
The price is £110 per night from 2 Sept to 3 Sept
£110
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very good! (1,608 reviews)
"Clean, comfortable and walking distance to Thompson's Point!"

Reviewed on 6 Aug 2026

Clarion Hotel Portland Airport ME
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Fully refundable
The price is £81 per night from 10 Aug to 11 Aug
£81
10 Aug - 11 Aug
includes taxes & fees
Quality Inn & Suites South Portland
See all 2,338 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Chebeague Island travel package cost?
Explore the best of Chebeague Island from as low as . Choose from a great selection of flights, hotels and rental cars to suit every budget and style. You can score even better deals when you add a few tours or activities to your travel package.
If I'm not able to travel, can I cancel my Chebeague Island travel package?
Certainly, and we'll help you every step of the way. You may be able to cancel or change your Chebeague Island travel package at no cost if you booked in the last 24 hours. However, you may incur a fee from your airline, hotel or car rental company for older bookings. If your circumstances suddenly change, browse our Customer Service Portal for further information.
How do I get a cheap travel package to Chebeague Island?
You'll save a ton of money if you combine your flights, car rentals and hotels into a Chebeague Island travel package. Sometimes cheap means fewer choices. But not with Expedia. We offer more than 550 air carriers and 1,000,000 properties throughout the world, so you'll always have plenty of variety to choose from. Like to save even more? Add some popular activities to your package deal and unlock even bigger discounts! After all, travel is about more than simply getting to your destination.
Does Expedia offer Book Now, Pay Later Chebeague Island holidays?
Your bank balance shouldn't stop you from taking a holiday, so Expedia has worked out a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a terrific getaway without eating away at your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your trip. Consider one of these flexible payment options:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that suit all types of budgets, so you can have that well-earned holiday sooner.
  • Pay in instalments holidays: Into the idea of paying for your holiday in multiple transactions? Then go for this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: Clicking the "book now" button is much easier with this payment option. Just put down a small deposit on your escape and then start packing your bags.

How far in advance should I book my Chebeague Island holiday?
Reserving your flight early with Expedia means one less thing to have to worry about. Many air carriers advertise tickets up to 12 months prior to departure dates. This is often the cheapest time to book. If circumstances have left you booking late, last-minute deals to Chebeague Island sometimes become available just weeks before departure.
What does an Expedia Chebeague Island travel package include?
Flights, rental cars and hotels — you'll find them all here. With Expedia, you can create your Chebeague Island travel package your way. All you have to do is figure out exactly what you need. Once you've made your booking, you can add on extras like activities and tours. The more you bundle, the greater the savings!
What should I know before booking a Chebeague Island travel package?
When you book your hotels, flights and car rentals together, you'll enjoy amazing discounts. Whether you're planning a beach break in a villa or would rather stay in a ritzy city hotel, Expedia can make it happen for less.
Can I choose my airline with a Chebeague Island Expedia travel package?
Yes, you can. We have more than 550 airline partners all over the world, so choose the carrier that suits your budget needs.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.