Chebeague Island Vacation Packages 2026 from $657

Chebeague Island flight + hotel vacation packages

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

Ogunquit River Inn & Suites

Moody

$657

per person

Sep 11 - Sep 13

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's a seasonal outdoor pool on site, and a terrace and a garden are also provided.

Blind Tiger Portland - Danforth Street.

West End

Save 100% on your flight

$1,897

per person

Oct 3 - Oct 6

found 17 hours ago

Roundtrip non-stop flight included

Kansas City (MCI) 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.

Inn at Diamond Cove

$1,386

per person

Sep 10 - Sep 15

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

A marina, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Make the most of the gym and outdoor tennis court, and relax with drinks at one of the 3 bars/lounges.

The Meadowmere Resort

$741

per person

Sep 11 - Sep 13

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.

The Docent's Collection at 121 Middle Street

Downtown Portland

Save 100% on your flight

$2,412

per person

Sep 10 - Sep 15

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

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

Top Chebeague Island hotels deals

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME

Free Cancellation

$93 nightly

$101 total

Sep 6 - Sep 7

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.

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free Cancellation

$131 nightly

$145 total

Sep 1 - Sep 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.

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Free Cancellation

$96 nightly

$104 total

Aug 30 - Aug 31

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.

Portland Regency Hotel & Spa

20 Milk Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$296 nightly

$328 total

Aug 30 - Aug 31

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.

Fireside Inn & Suites Portland

81 Riverside St Portland ME

Free Cancellation

Reserve now, pay when you stay

$113 nightly

$125 total

Sep 1 - Sep 2

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.

Waves Oceanfront Resort

87 W Grand Ave Old Orchard Beach ME

$190 nightly

$207 total

Aug 30 - Aug 31

Total with taxes and fees

This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A coffee shop, a lobby fireplace, and a picnic area are also on offer.

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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 $657. 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.