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
Save 100% on your flight
Price was $1,166, price is now $730 per person
$730
per person
Jul 12 - Jul 16
found 22 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Meadowmere Resort

Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,412, price is now $917 per person
$917
per person
Jul 12 - Jul 16
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
This smoke-free hotel features 2 hot tubs, an indoor pool, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.
Saco Bay Hotel

Saco Bay Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,440, price is now $986 per person
$986
per person
Jul 18 - Jul 24
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the business center and WiFi in public areas. Enjoy the outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,941, price is now $2,058 per person
$2,058
per person
Jul 18 - Jul 24
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
This hotel features free WiFi in public areas, a virtual front desk, and self parking. Express check-out is also provided.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $2,499, price is now $1,753 per person
$1,753
per person
Jul 12 - Jul 16
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center, laundry service, and valet parking. Relax with a drink at one of the 2 poolside bars and enjoy perks like free self parking.

Top Chebeague Island hotels deals

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
$221 nightly
The price is $244 total per night
$244 total
May 10 - May 11
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
Free Cancellation
Reserve now, pay when you stay
$161 nightly
The price is $178 total per night
$178 total
May 26 - May 27
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
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
$169 nightly
The price is $187 total per night
$187 total
May 26 - May 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 and free WiFi in public areas. Self parking and a safe deposit box are also offered on site.
Pet friendly
Free WiFi
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free Cancellation
$88 nightly
The price is $98 total per night
$98 total
May 12 - May 13
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
HomeAwhile

HomeAwhile

4 out of 5
205 Southborough Drive Scarborough ME
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $127 total per night
$127 total
May 7 - May 8
Total with taxes and fees
This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Pet friendly
Parking included
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

4 out of 5
88 Spring St Portland ME
Free Cancellation
$118 nightly
The price is $131 total per night
$131 total
May 10 - May 11
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free area shuttle.
Pool
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 $730. 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

Early morning harbor in Maine
Early morning harbor in Maine
Tranquil golf course landscape featuring a stunning sunset. Chebeague Island, Maine, USA.

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