Chebeague Island Vacation Packages 2026 from $965

Chebeague Island flight + hotel vacation packages

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

AWOL Kennebunkport

$965

per person

Oct 26 - Oct 30

found 21 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

This hotel features free WiFi in public areas, concierge services, and free self parking. Enjoy the free buffet breakfast each morning. Express check-out and luggage storage are also provided.

Evalina Hotel

Downtown Portland

Save 100% on your flight

$1,805

per person

Oct 19 - Oct 24

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

Save 100% on your flight

$1,939

per person

Oct 19 - Oct 24

found 1 day ago

Roundtrip 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.

Ogunquit River Inn & Suites

Moody

$1,087

per person

Sep 26 - Oct 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Inn By The Sea

Save 100% on your flight

$2,240

per person

Sep 26 - Oct 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the playground, onsite laundry facilities, and free supervised childcare. Enjoy the outdoor pool and perks like free valet parking.

Top Chebeague Island hotels deals

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME

Free Cancellation

$98 nightly

$106 total

Sep 3 - Sep 4

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

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.

Pool

Hot Tub

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Free Cancellation

$97 nightly

$105 total

Aug 10 - Aug 11

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

Portland Regency Hotel & Spa

20 Milk Street Portland ME

$293 nightly

$324 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.

Hot Tub

Spa

Fireside Inn & Suites Portland

81 Riverside St Portland ME

Free Cancellation

Reserve now, pay when you stay

$115 nightly

$127 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.

Pool

Hot Tub

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 $965. 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.