Chebeague Island Vacations from $629

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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.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
per person
Nov 4 - Nov 7
found 21 hours ago
Roundtrip non-stop flight included
Richmond (RIC) to Portland (PWM)
9.6/10 Exceptional! (121 reviews)
This was such a fun and cool place to stay! We really enjoyed this location and would definitely recommend it to anyone staying in the area. Be sure to check out the super cool basement pool room!

Reviewed on Sep 21, 2024

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.2/10 Wonderful! (1,319 reviews)
Beautiful hotel, spacious rooms, within walking distance to shops and restaurants. Friendly and helpful staff

Reviewed on Sep 22, 2024

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (172 reviews)
Great spot for downtown Portland

Reviewed on Sep 11, 2024

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
per person
Nov 4 - Nov 7
found 21 hours ago
Roundtrip non-stop flight included
Richmond (RIC) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Love staying in old B&B houses that have been tastefully modernized inside. Staff was very helpful with accommodations.

Reviewed on Sep 16, 2024

Inn By The Sea

Inn By The Sea

4 out of 5
per person
Nov 4 - Nov 8
found 23 hours ago
Roundtrip non-stop flight included
Richmond (RIC) to Portland (PWM)
9.6/10 Exceptional! (234 reviews)
Lovely property with beautiful views. We enjoyed our stay very much!!

Reviewed on Sep 14, 2024

Chebeague Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Max Temp Winter
30ºF
Max Temp Summer
70ºF
Top Sights
State Theatre, East End Beach and Portland Museum of Art

Ready to book your vacation to Chebeague Island?

 

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Chebeague Island Hotel Deals

Casco Bay Hotel, Ascend Hotel Collection
Casco Bay Hotel, Ascend Hotel Collection
3.5 out of 5
80 John Roberts Rd., South Portland, ME
Fully refundableReserve now, pay when you stay
The price is $86 per night from Oct 20 to Oct 21
$86
includes taxes & fees
$79 per night
Oct 20 - Oct 21
8.4/10 Very Good! (2,108 reviews)
"A"

Reviewed on Sep 21, 2024

Casco Bay Hotel, Ascend Hotel Collection
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 $124 per night from Oct 21 to Oct 22
$124
includes taxes & fees
$112 per night
Oct 21 - Oct 22
7.6/10 Good! (1,029 reviews)
"The staff was very friendly and courtesy"

Reviewed on Sep 21, 2024

Ramada Plaza 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 $279 per night from Sep 29 to Sep 30
$279
includes taxes & fees
$253 per night
Sep 29 - Sep 30
8.6/10 Excellent! (1,003 reviews)
"Centrally located."

Reviewed on Sep 19, 2024

The Westin Portland Harborview
See all 2,063 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.

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Frequently asked questions

How much does a Chebeague Island vacation package cost?
You’ll find cheap prices from $629 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 filter tool to find some of the best Chebeague Island package deals. When you begin your search, just set your maximum budget and then sort the results by “Price: low to high.” If you’re looking to save, plan your adventure for midweek, or look for Chebeague Island package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it’s typically best to lock in 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?
Score amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Chebeague Island trip.
How to plan a trip to Chebeague Island?

  1. Choose your dates: The things you’d like to do in Chebeague Island and your preferred season can help you decide when to get away.
  2. Set a budget: Factor in costs such as flights, meals and transportation when calculating how much to set aside for your trip to Chebeague Island. Then, pick a property that works with your budget, whether that’s a low-cost option or a lavish retreat.
  3. Use Expedia’s trip planning tool to explore Chebeague Island: Research every part of your trip to Chebeague Island with this comprehensive planner. Invite family or friends to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Set the duration of your trip: Start by compiling a list of the activities and sights you want to experience in Chebeague Island. Then, estimate how long you’ll need at each, along with any travel time.
  5. Bundle your accommodations and airfare: Once you’ve nailed down your travel dates and duration, book the ideal Chebeague Island vacation package for you.
  6. Add on experiences and excursions: Have a look at our travel guide to find some exciting things to do in Chebeague Island. Book tickets or make reservations in advance to save time and avoid the hassle of looking for activities when you arrive.

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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.