Chebeague Island Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Chebeague Island

Chebeague Island Inn
Chebeague Island Inn
4 out of 5
61 South Road, Chebeague Island, ME
The price is 7.813.365 ₫ per night from 27 Jul to 28 Jul
7.813.365 ₫
10.304.916 ₫ total
27 Jul - 28 Jul
includes taxes & fees
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

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
Fully refundableReserve now, pay when you stay
The price is 4.437.455 ₫ per night from 7 Jul to 8 Jul
4.437.455 ₫
4.909.600 ₫ total
7 Jul - 8 Jul
includes taxes & fees
8.8/10 Excellent! (2,169 reviews)
"We only stayed one night; arrived late and left early, but it was a clean property, comfortable bed and good breakfast. It is away from the downtown area, and it would be difficult if you were wanting to walk back and forth, but otherwise it was a comfortable stay. I can't really comment on the area ..."

Reviewed on 25 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
Fully refundableReserve now, pay when you stay
The price is 7.019.555 ₫ per night from 29 Jun to 30 Jun
7.019.555 ₫
7.766.435 ₫ total
29 Jun - 30 Jun
includes taxes & fees
8.8/10 Excellent! (1,146 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 2,325 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.