Chebeague Island Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Chebeague Island Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Best Western Freeport Inn
Price was $791, price is now $636 per person
$636
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Stay at this hotel in Freeport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LL Bean Flagship Store and Eartha are located nearby.
The room was fine, but we hadn’t expected to have to walk up stairs to get to our room in a three floor facility. Although it was only a half flight, it was inconvenient. Also, breakfast was not included in the price. There was a good breakfast available near by.
Reviewed on Jun 29, 2026
Saco Bay Hotel
Save 100% on your flight
Price was $1,153, price is now $842 per person
$842
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Book a stay at this business-friendly hotel in Saco. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Orchard Beach and Saco Museum are located nearby.
Clean and well maintained
Reviewed on Jul 1, 2026
Hampton Inn Portland Downtown - Waterfront
Downtown Portland
Save 100% on your flight
Price was $1,694, price is now $1,387 per person
$1,387
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Casco Bay Lines Ferry Terminal and State Theatre are located nearby.
Well maintained. But not easy parking. $40 per night.
Reviewed on Jul 2, 2026
Clarion Hotel Portland Airport ME
Price was $820, price is now $697 per person
$697
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and State Theatre are located nearby.
My family and I were in Maine for a long weekend. We have stayed here before and had good luck. Our room and bathroom were clean and the water was hot for showers. The only thing we didn’t like was that we were put at the end of the hallway right across from the elevator so we heard the elevator all night. The second thing that we didn’t like is that there was a concert going on and the concert goers were parking in the hotel lot. Once we got back from dinner and the beach there was no parking for hotel guests. We did end up finding one spot after driving in circles for a bit. The pool and work out room were cleaned and everyone seemed to be enjoying it.
Reviewed on Jun 28, 2026
Inn at St John Portland In-Town
Valley Street
Price was $1,238, price is now $1,073 per person
$1,073
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and State Theatre are located nearby.
Very cool stay!
Reviewed on Jun 30, 2026
Dormir
Price was $1,022, price is now $886 per person
$886
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Book a stay at this business-friendly hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sebago Lake and Seacoast Adventure are located nearby.
Convenient to the lake
Reviewed on Jun 28, 2026
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See all available trips from Columbus to Chebeague Island
View all tripsChebeague Island Vacation Packages
Trying to plan a way to bundle your Chebeague Island flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® can help you get everything you need, while saving you both money and some time. We're here to book everything you'll need to make your Chebeague Island trip one to remember. Our Travel Center is a one-stop shop where you can put together the best Chebeague Island vacation package for you and your family. AARP Travel Center has a huge selection of flights and hotels, as well as local activities to select from.
Hotels in Chebeague Island
Our listings include accommodations that are close to all the Chebeague Island points of interest, and others that are just outside the city center for a more restful retreat.
We have fantastic rates on everything from all-inclusive resorts that meet all the vacation must-haves to inexpensive hotels perfect for those on wanting to save a little money. You can look through all the options and select the accommodation that is perfect for you. With AARP Travel Center's Chebeague Island hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.
Things to do in Chebeague Island
Chebeague Island is the perfect spot when you need to a break from it all. With only around 349 people here, this cozy town is just right for a quite vacation. If you want to take walk through the past, then you are in luck as Chebeague Island has a fascinating historic district.
Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.
Book Together and Save
With so much to see and do in Chebeague Island, you'll be wanting to plan your itinerary, not spending time to finding the hotel with the lowest rate. AARP Travel Center allows you to easily reserve everything you need, and save some cash at the same time. You can plan your entire holiday, including things to do in Chebeague Island from only one site. The hardest packing you'll have to do is for your suitcase. Book today and save!
Top Hotel Deals
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave Portland ME
16.97 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Portland Harbor Hotel
468 Fore Street Portland ME
15.28 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff ...
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
14.45 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
20.91 km from city center
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's ...
Comfort Inn South Portland Airport
90 Maine Mall Rd South Portland ME
21.19 km from city center
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
Portland Regency Hotel & Spa
20 Milk Street Portland ME
15 km from city center
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Quality Inn & Suites South Portland
738 Main Street South Portland ME
21.16 km from city center
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
21.73 km from city center
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
15.73 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
The Westin Portland Harborview
157 High St Portland ME
15.88 km from city center
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Waves Oceanfront Resort
87 W Grand Ave Old Orchard Beach ME
33.79 km from city center
Book a stay at this beach hotel in Old Orchard Beach. Enjoy free parking, an outdoor pool, and a beach locale. Our guests praise the helpful staff and the clean ...
Hampton Inn Portland Downtown - Waterfront
209 Fore St Portland ME
14.72 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Grand Beach Inn
198 East Grand Avenue Old Orchard Beach ME
30.86 km from city center
Stay at this hotel in Old Orchard Beach. Enjoy free WiFi, free parking, and room service. Our guests praise the restaurant and the helpful staff in our reviews. ...
Don't see what you're looking for?
See all available properties in Chebeague Island
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Jul 28 - Thu, Aug 6
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$157 Roundtrip, found 17 hours ago
$157
Roundtrip
found 17 hours ago
Tue, Sep 8 - Fri, Sep 11
LGA
LaGuardia
PWM
Portland Intl. Jetport
$168 Roundtrip, found 5 days ago
$168
Roundtrip
found 5 days ago
Tue, Sep 8 - Fri, Sep 11
LGA
LaGuardia
PWM
Portland Intl. Jetport
$185 Roundtrip, found 5 days ago
$185
Roundtrip
found 5 days ago
Thu, Sep 17 - Sat, Sep 26
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$193 Roundtrip, found 6 days ago
$193
Roundtrip
found 6 days ago
Wed, Oct 7 - Wed, Oct 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$194 Roundtrip, found 20 hours ago
$194
Roundtrip
found 20 hours ago