Deals on vacations and trips to Chebeague Island

Save when you book Chebeague Island package deals

Choose two or more items and save on your trip:

Chebeague Island flight + hotel vacation packages

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

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $607, price is now $468 per person
$468
per person
Jan 13 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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.
The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Downtown Portland
Price was $740, price is now $570 per person
$570
per person
Jan 13 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Portland (PWM)
This hotel features free WiFi in public areas, concierge services, and self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Luggage storage is also provided.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,419, price is now $1,149 per person
$1,149
per person
Dec 7 - Dec 12
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
This bed & breakfast doesn't skimp on freebies - guests receive free breakfast and free WiFi. Luggage storage and concierge services are also provided.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $1,399, price is now $1,134 per person
$1,134
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
A full-service spa, 2 restaurants, and an indoor pool 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

The Docent's Collection

3.5 out of 5
Downtown Portland
Price was $650, price is now $537 per person
$537
per person
Jan 13 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Portland (PWM)
This hotel features free WiFi in public areas, a virtual front desk, and self parking. Express check-out is provided and the front desk is staffed around-the-clock.

Top Chebeague Island hotels deals

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Free Cancellation
Reserve now, pay when you stay
$165 nightly
The price is $183 total per night
$183 total
Nov 30 - Dec 1
Total with taxes and fees
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.
Pet friendly
Free WiFi
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Free Cancellation
Reserve now, pay when you stay
$83 nightly
The price is $92 total per night
$92 total
Nov 11 - Nov 12
Total with taxes and fees
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
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road, South Portland, ME
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $88 total per night
$88 total
Nov 16 - Nov 17
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free self parking, and a free airport shuttle. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Free airport shuttle
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street, Portland, ME
$145 nightly
The price is $161 total per night
$161 total
Nov 13 - Nov 14
Total with taxes and fees
A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and a roundtrip airport shuttle. There's a gym on site, and laundry facilities and concierge services are also offered.
Hot Tub
Spa
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave, Portland, ME
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $110 total per night
$110 total
Nov 6 - Nov 7
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and a free airport shuttle. Business travelers can take advantage of the business center. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
Pool
Breakfast included
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

4 out of 5
88 Spring St, Portland, ME
Free Cancellation
$78 nightly
The price is $86 total per night
$86 total
Nov 30 - Dec 1
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free area shuttle.
Pool
Free airport shuttle
Don't see what you're looking for?
See all available properties in Chebeague Island
View all properties
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 $468. 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.

Photos of local treasures

Browse Chebeague Island vacation photos for more inspiration

Explore More Ways to Travel with Travelocity