Chebeague Island Vacation Packages 2026 from $478

Chebeague Island flight + hotel vacation packages

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

The Westin Portland Harborview

Downtown Portland

$478

per person

Apr 29 - May 3

found 24 hours ago

Roundtrip flight included

New York (JFK) 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 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.

The Docent’s Collection – Thompson Block

Downtown Portland

$619

per person

Apr 29 - May 3

found 24 hours ago

Roundtrip flight included

New York (JFK) 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.

Portland Harbor Hotel

Downtown Portland

$598

per person

Apr 29 - May 3

found 24 hours ago

Roundtrip flight included

New York (JFK) 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.

Blind Tiger Portland - Danforth Street.

West End

Save 100% on your flight

$935

per person

Apr 29 - May 3

found 24 hours ago

Roundtrip flight included

New York (JFK) 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

Bald Head

$1,366

per person

Apr 9 - Apr 12

found 1 day ago

Roundtrip flight included

Chicago (ORD) 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.

Top Chebeague Island hotels deals

Long Creek Hotel by IHG

171 Philbrook Ave South Portland ME

Free Cancellation

$83 nightly

$90 total

Feb 6 - Feb 7

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like on-the-go breakfast and free self parking.

Portland Harbor Hotel

468 Fore Street Portland ME

$145 nightly

$160 total

Feb 9 - Feb 10

Total with taxes and fees

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$85 total

Feb 8 - Feb 9

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.

Portland Regency Hotel & Spa

20 Milk Street Portland ME

$153 nightly

$169 total

Feb 5 - Feb 6

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.

Hyatt Place Portland Downtown - Old Port Square

433 Fore St Portland ME

Free Cancellation

Reserve now, pay when you stay

$90 nightly

$100 total

Mar 2 - Mar 3

Total with taxes and fees

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Valet parking, a coffee shop, and a snack bar/deli are also offered.

Canopy by Hilton Portland Waterfront

9 Center Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$112 nightly

$124 total

Feb 10 - Feb 11

Total with taxes and fees

This hotel features 2 restaurants and a 24-hour gym. WiFi in public areas is free. Valet parking, a lobby fireplace, and a communal living room are also offered.

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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 $478. 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.