Deals on vacations and trips to Chebeague Island

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Chebeague Island flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was $1,156, price is now $823 per person
$823
per person
Oct 19 - Oct 24
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.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $3,222, price is now $1,998 per person
$1,998
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.
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,545, price is now $1,682 per person
$1,682
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.
Chebeague Island Inn

Chebeague Island Inn

4 out of 5
Save 100% on your flight
Price was $1,533, price is now $1,059 per person
$1,059
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate perks like free WiFi and a free ferry terminal shuttle. A garden, a lobby fireplace, and a picnic area are also on offer.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,569, price is now $1,126 per person
$1,126
per person
Oct 10 - Oct 15
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.

Top Chebeague Island hotels deals

Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
Free Cancellation
$77 nightly
The price is $83 total per night
$83 total
Sep 1 - Sep 2
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

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free Cancellation
$131 nightly
The price is $145 total per night
$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

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Free Cancellation
$94 nightly
The price is $102 total per night
$102 total
Sep 8 - Sep 9
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
Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

2.5 out of 5
90 Maine Mall Rd South Portland ME
Free Cancellation
$120 nightly
The price is $130 total per night
$130 total
Sep 7 - Sep 8
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
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $108 total per night
$108 total
Sep 9 - Sep 10
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
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$314 nightly
The price is $348 total per night
$348 total
Sep 8 - Sep 9
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
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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 $823. 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.

Photos of local treasures

Browse Chebeague Island vacation photos for more inspiration

A wooden pier leading to a marina with boats docked.
A calm harbor with several sailboats anchored in the water.
A sunset over a calm lake with boats, a pier, and a grassy field.

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