Chebeague Island Vacation Packages 2026 from $664

Chebeague Island flight + hotel vacation packages

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

The Meadowmere Resort

$664

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

2 hot tubs, an indoor pool, and a gym are all featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. There's a restaurant and a bar/lounge for dining and drinks, and also a sauna on site.

Blind Tiger Portland – Carleton Street

West End

$959

per person

Dec 5 - Dec 10

found 8 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

Free WiFi in public areas, a terrace, and a garden are available at this bed & breakfast. Enjoy the free on-the-go breakfast each morning. Concierge services are provided for your convenience.

Evalina Hotel

Downtown Portland

$1,102

per person

Nov 21 - Nov 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

Free WiFi in public areas is available at this aparthotel. Take advantage of the self parking.

Blind Tiger Portland - Danforth Street.

West End

$1,106

per person

Dec 5 - Dec 10

found 8 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) 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.

The Docent's Collection at 178 Middle Street

Downtown Portland

$959

per person

Nov 21 - Nov 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

This hotel features free WiFi in public areas, concierge services, and self parking. Express check-in and luggage storage are also provided.

Top Chebeague Island hotels deals

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Free Cancellation

$87 nightly

$95 total

Oct 18 - Oct 19

Total with taxes and fees

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

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

80 John Roberts Rd. South Portland ME

Free Cancellation

$110 nightly

$120 total

Oct 18 - Oct 19

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Business travelers can take advantage of the free WiFi in public areas. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.

Breakfast included

Free airport shuttle

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$119 total

Oct 18 - Oct 19

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

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME

Free Cancellation

$51 nightly

$56 total

Oct 20 - Oct 21

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and WiFi in public areas. Enjoy the indoor pool and free perks like continental breakfast and free self parking.

Pool

Breakfast included

Comfort Inn South Portland Airport

90 Maine Mall Rd South Portland ME

Free Cancellation

$109 nightly

$119 total

Oct 18 - Oct 19

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and a free airport shuttle. Traveling on business? Take advantage of the express check-out, laundry service, and free train station pick-up. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Free airport shuttle

Portland Harbor Hotel

468 Fore Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$453 nightly

$502 total

Oct 18 - Oct 19

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

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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 $664. 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.