Chebeague Island Vacation Packages 2026 from $589

Chebeague Island flight + hotel vacation packages

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

Admiral Peary Inn

$589

per person

Nov 5 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Portland (PWM)

This bed & breakfast doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A coffee shop, a garden, and a snack bar/deli are also on offer.

Evalina Hotel

Downtown Portland

$1,147

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Portland (PWM)

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

Inn By The Sea

Save 100% on your flight

$1,191

per person

Dec 15 - Dec 22

found 9 hours ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

The Docent's Collection at 178 Middle Street

Downtown Portland

$983

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) 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.

84 Main

$867

per person

Nov 20 - Nov 25

found 19 hours ago

Roundtrip flight included

Denver (DEN) to Portland (PWM)

This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. Luggage storage and laundry facilities are also provided.

Top Chebeague Island hotels deals

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free Cancellation

Reserve now, pay when you stay

$71 nightly

$78 total

Nov 1 - Nov 2

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

The Westin Portland Harborview

157 High St Portland ME

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$149 total

Nov 1 - Nov 2

Total with taxes and fees

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

Fireside Inn & Suites Portland

81 Riverside St Portland ME

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$96 total

Oct 29 - Oct 30

Total with taxes and fees

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

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Free Cancellation

$65 nightly

$71 total

Nov 5 - Nov 6

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

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME

Free Cancellation

$51 nightly

$56 total

Nov 5 - Nov 6

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

Inn at St John Portland In-Town

939 Congress St Portland ME

$93 nightly

$101 total

Oct 20 - Oct 21

Total with taxes and fees

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A lobby fireplace, a computer station, and luggage storage are also on offer.

Breakfast included

Pet friendly

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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 $589. 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.