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 $1,100, price is now $679 per person
$679
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) 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.
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,748, price is now $1,050 per person
$1,050
per person
Sep 21 - Sep 25
found 13 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Portland (PWM)
Free WiFi in public areas is available at this aparthotel. Take advantage of the self parking.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $1,500, price is now $948 per person
$948
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) 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

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was $1,447, price is now $972 per person
$972
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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 – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Save 100% on your flight
Price was $1,348, price is now $906 per person
$906
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) to Portland (PWM)
Free WiFi in public areas, a terrace, and a garden are available at this bed & breakfast. Enjoy the free on-the-go breakfast each morning. Concierge services are provided for your convenience.

Top Chebeague Island hotels deals

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $165 total per night
$165 total
Jul 5 - Jul 6
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the free on-the-go breakfast each morning.
Pool
Breakfast included
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$333 nightly
The price is $369 total per night
$369 total
Jul 5 - Jul 6
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
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Free Cancellation
Reserve now, pay when you stay
$270 nightly
The price is $299 total per night
$299 total
Jul 12 - Jul 13
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
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 12 - Jul 13
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
$129 nightly
The price is $141 total per night
$141 total
Jul 5 - Jul 6
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
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
$208 nightly
The price is $230 total per night
$230 total
Jul 6 - Jul 7
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 $679. 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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