Chebeague Island Vacation Packages 2026 from $562

Chebeague Island flight + hotel vacation packages

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

Portland Harbor Hotel

Downtown Portland

$562

per person

Jan 25 - Jan 29

found 20 hours ago

Roundtrip non-stop flight included

Houston (HOU) to Portland (PWM)

This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.

Cliff House Maine

Bald Head

$945

per person

Jan 21 - Jan 24

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Portland (PWM)

A full-service spa, 2 restaurants, and a 24-hour gym are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center, laundry service, and valet parking. Relax with a drink at one of the 2 poolside bars and enjoy perks like free self parking.

The Docent's Collection at 121 Middle Street

Downtown Portland

$786

per person

Jan 25 - Jan 29

found 20 hours ago

Roundtrip non-stop flight included

Houston (HOU) to Portland (PWM)

This hotel features free WiFi in public areas, a virtual front desk, and self parking. Express check-out is also provided.

Inn By The Sea

$636

per person

Jan 21 - Jan 24

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Portland (PWM)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, laundry service, and free valet parking. Enjoy the outdoor pool and unwind at the bar/lounge and poolside bar.

Blind Tiger Portland - Danforth Street.

West End

$782

per person

Jan 25 - Jan 29

found 20 hours ago

Roundtrip non-stop flight included

Houston (HOU) to Portland (PWM)

This bed & breakfast features free WiFi in public areas, concierge services, and self parking. Enjoy the free self-serve breakfast each morning. Luggage storage is also provided.

Top Chebeague Island hotels deals

The Westin Portland Harborview

157 High St Portland ME

Free Cancellation

Reserve now, pay when you stay

$112 total

per night

Dec 6 - Dec 7

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

Spa

Pet friendly

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free Cancellation

$89 total

per night

Nov 12 - Nov 13

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and perks like free self parking and a free cruise terminal shuttle.

Pool

Hot Tub

Fireside Inn & Suites Portland

81 Riverside St Portland ME

Free Cancellation

Reserve now, pay when you stay

$97 total

per night

Nov 9 - Nov 10

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.

Pool

Hot Tub

Portland Harbor Hotel

468 Fore Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$180 total

per night

Nov 22 - Nov 23

Pet friendly

Free WiFi

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Free Cancellation

$66 total

per night

Nov 12 - Nov 13

This hotel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.

Breakfast included

Pet friendly

Ramada Plaza by Wyndham Portland

155 Riverside St Portland ME

Free Cancellation

Reserve now, pay when you stay

$86 total

per night

Nov 11 - Nov 12

This hotel features 2 restaurants, 2 hot tubs, and an indoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Hot Tub

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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 are vacation packages to Chebeague Island?

Travelocity offers flight and hotel vacation packages from just $562. With these kinds of deals, you'll be saying hello to Chebeague Island in a flash.

Where can I get the best vacation package deals for Chebeague Island?

Travelocity will be able to help you snag an awesome Chebeague Island package deal. With as many as 400 airlines and 1,000,000 properties across the globe, you're bound to be able to craft the perfect itinerary.

Why should I purchase my Chebeague Island vacation package via Travelocity?

Savings, support and a stress-free booking are just the tip of the iceberg. Enjoy a fulfilling travel experience knowing you have access to our team of customer support experts around-the-clock. With the Travelocity Price Match Guarantee, you can rest easy knowing you're getting the best deal available.

Can I save on my Chebeague Island car rental if I combine it with my hotel or flight?

You can with our Chebeague Island vacation packages. With one of these, there are lots of ways to make your vacation budget go further. Bundle any two or more car, hotel, flight and tour bookings and see the savings pile up. With your own ride, all the popular sights around Chebeague Island are a fun road trip away.