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.
River View Resort

River View Resort

2.5 out of 5
Save 100% on your flight
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
This motel features an indoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. Enjoy the sauna and conveniences like a terrace and barbecue grills.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A garden, luggage storage, and concierge services are also on offer.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
This hotel doesn't skimp on freebies - guests receive 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.
Chebeague Island Inn

Chebeague Island Inn

4 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) 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.

Top Chebeague Island hotels deals

Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $168 total per night
$168 total
Aug 11 - Aug 12
Total includes 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
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $120 total per night
$120 total
Aug 24 - Aug 25
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Comfort Inn Airport

Comfort Inn Airport

2.5 out of 5
90 Maine Mall Rd, South Portland, ME
Free Cancellation
Reserve now, pay when you stay
$134 nightly
The price is $146 total per night
$146 total
Aug 5 - Aug 6
Total includes 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
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $145 total per night
$145 total
Sep 1 - Sep 2
Total includes taxes and fees
2 hot tubs, an indoor pool, and a gym are all featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the a restaurant and perks like free self parking.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Free Cancellation
Reserve now, pay when you stay
$340 nightly
The price is $376 total per night
$376 total
Sep 1 - Sep 2
Total includes 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.
Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

3.5 out of 5
80 John Roberts Rd., South Portland, ME
Free Cancellation
Reserve now, pay when you stay
$159 nightly
The price is $173 total per night
$173 total
Aug 4 - Aug 5
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Business travelers can take advantage of the free WiFi in public areas. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.
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 $738. 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.

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