Chebeague Island Vacations from $380

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Chebeague Island Vacation

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

The Latest Chebeague Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Dormir

Dormir

3 out of 5
Save 100% on your flight
Price was $518, price is now $380 per person
$380
per person
Oct 14 - Oct 17
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
8.8/10 Excellent! (1,003 reviews)
For the price I would have liked to have my bed made and fresh towels replaced every day. Breakfast was really good but ditch those fake eggs. Over all it was great. Would stay there again.

Reviewed on Aug 17, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,741, price is now $1,147 per person
$1,147
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!

Reviewed on Aug 9, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $760, price is now $526 per person
$526
per person
Oct 27 - Oct 30
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (226 reviews)
I had a wonderful stay! The place was clean, cozy, and exactly as described. The location was perfect, which made everything smooth and easy. I’d happily stay here again and recommend it to anyone visiting Portland.

Reviewed on Aug 22, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $2,276, price is now $1,709 per person
$1,709
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (279 reviews)
We chose Inn by the Sea because it was advertised as a “pet-friendly” property with beach access for pets, which was a key factor in our decision. Unfortunately, our experience didn’t quite align with those expectations. We arrived on a Sunday around noon and, as expected, our room wasn’t ready (check-in is at 4:00pm). However, unlike many hotels, we were not offered anything while we waited — no welcome drink, light refreshment, or even an early check-in estimate — despite having to wait the full four hours. Once we checked in, we were told our assigned room was not pet-friendly, and we would be charged for any accidents — despite booking under the premise that this was a pet-friendly stay. Additionally, the restaurant only allows pets in the outdoor seating area, and the pool area is not pet-friendly at all. So while the hotel does accommodate pets in some areas, it’s misleading to call it fully pet-friendly when the main guest amenities are off-limits. That said, the property is beautiful and most of the staff were friendly and professional, which we appreciated. But overall, if you’re traveling with a pet and hoping for a truly integrated experience, this may not be the best fit.

Reviewed on Aug 18, 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $987, price is now $744 per person
$744
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.8/10 Exceptional! (68 reviews)
nice building walkable to shopping + dining

Reviewed on Aug 22, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chebeague Island
View all trips

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
$107 nightly
The price is $117 total per night from Aug 26 to Aug 27
$117 total
Aug 26 - Aug 27
Total with taxes and 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
$152 nightly
The price is $168 total per night from Aug 27 to Aug 28
$168 total
Aug 27 - Aug 28
Total with taxes and 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
$128 nightly
The price is $141 total per night from Sep 2 to Sep 3
$141 total
Sep 2 - Sep 3
Total with taxes and 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chebeague Island vacation package cost?
You'll find cheap prices from $380 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?
If you'd like to book a cheap Chebeague Island vacation package, consider planning a trip in November, December and January. You'll typically find better prices on hotels and airfares during these months — perfect for budget-conscious travelers.
How many days is enough for Chebeague Island?
With a well-planned schedule, you can easily visit the top Chebeague Island attractions in a few days. But if you prefer to discover hidden spots or go on day trips, consider booking your Chebeague Island vacation for longer.
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.
Does Expedia offer Book Now, Pay Later Chebeague Island vacation packages?
Jet off on your dream escape to Chebeague Island with our Book Now, Pay Later vacations. There's no need to save up or wait for your next payday — we've joined forces with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to budget for your trip and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.