Chebeague Island Vacations

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Find the Best Chebeague Island Vacation Packages

Chebeague Island Hotel Deals

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 ₩148,181 per night from Aug 26 to Aug 27
₩148,181
₩161,518 total
Aug 26 - Aug 27
includes taxes & fees
7.8/10 Good! (1,223 reviews)
Excellent choice for single night stay
"Very convenient hotel for those flying into PWM. Quick stop on the way to Rockland. Front desk was pleasant. Got me toothpaste I forgot. Told them about stopped up sink and they noted it. (It wasn't an issue for me as I simply removed the stopper and left it on the counter to be cleaned.) Breakfast ..."

Reviewed on Aug 22, 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 ₩210,512 per night from Aug 27 to Aug 28
₩210,512
₩232,909 total
Aug 27 - Aug 28
includes taxes & fees
7.8/10 Good! (1,004 reviews)
"I like the room and accommodations. The front desk person was a bit brief with me though."

Reviewed on Aug 22, 2025

Clarion Hotel Portland
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is ₩176,406 per night from Sep 2 to Sep 3
₩176,406
₩195,167 total
Sep 2 - Sep 3
includes taxes & fees
7.8/10 Good! (1,045 reviews)
"Property is good . Nice area and convenient"

Reviewed on Aug 22, 2025

Ramada Plaza by Wyndham Portland
See all 2,280 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 vacation 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 vacation 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 vacation 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 vacation. 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 vacation package as soon as possible.
Is it cheaper to book a Chebeague Island vacation as a package?
Expedia vacation 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 customized Chebeague Island vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation 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 vacation 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 vacation 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.