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.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Save 100% on your flight
Price was $1,407, price is now $899 per person
$899
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $2,223, price is now $1,395 per person
$1,395
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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 $2,174, price is now $1,388 per person
$1,388
per person
Sep 22 - Sep 26
found 13 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
Free WiFi in public areas is available at this aparthotel. Take advantage of the self parking.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Save 100% on your flight
Price was $1,929, price is now $1,312 per person
$1,312
per person
Aug 15 - Aug 21
found 6 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,520, price is now $1,038 per person
$1,038
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free Cancellation
$144 nightly
The price is $159 total per night
$159 total
Jul 26 - Jul 27
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
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
$297 nightly
The price is $328 total per night
$328 total
Jul 26 - Jul 27
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A safe deposit box is provided and the front desk is staffed around-the-clock.
Pet friendly
Free WiFi
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
$433 nightly
The price is $480 total per night
$480 total
Jul 26 - Jul 27
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
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
$359 nightly
The price is $397 total per night
$397 total
Aug 9 - Aug 10
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
Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
Free Cancellation
$90 nightly
The price is $98 total per night
$98 total
Jul 26 - Jul 27
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

Comfort Inn South Portland Airport

2.5 out of 5
90 Maine Mall Rd South Portland ME
Free Cancellation
Reserve now, pay when you stay
$148 nightly
The price is $161 total per night
$161 total
Jul 19 - Jul 20
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
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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 $899. 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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