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.
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was $1,058, price is now $792 per person
$792
per person
Jun 8 - Jun 11
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
This hotel features free WiFi in public areas, a virtual front desk, and self parking. Express check-out is also provided.
Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
Save 100% on your flight
Price was $1,299, price is now $821 per person
$821
per person
Jun 28 - Jul 3
found 1 hour ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
This hotel features 2 outdoor tennis courts, an outdoor pool, and a restaurant. There's fun for all ages with a bowling alley and a playground, and families will appreciate the picnic area. Enjoy the gym and perks like free self parking and free WiFi.
Ramada by Wyndham Saco/Old Orchard Beach Area

Ramada by Wyndham Saco/Old Orchard Beach Area

2.5 out of 5
Price was $1,282, price is now $933 per person
$933
per person
Jul 7 - Jul 12
found 3 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $1,410, price is now $1,035 per person
$1,035
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
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.
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,811, price is now $1,351 per person
$1,351
per person
Jun 8 - Jun 11
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the playground, onsite laundry facilities, and free supervised childcare. Enjoy the outdoor pool and perks like free valet parking.

Top Chebeague Island hotels deals

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $135 total per night
$135 total
Apr 19 - Apr 20
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.
Spa
Pet friendly
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
$134 nightly
The price is $149 total per night
$149 total
Apr 21 - Apr 22
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
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $165 total per night
$165 total
Apr 26 - Apr 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
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
$93 nightly
The price is $103 total per night
$103 total
Apr 20 - Apr 21
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
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
$122 nightly
The price is $135 total per night
$135 total
Apr 22 - Apr 23
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
Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
433 Fore St Portland ME
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $119 total per night
$119 total
Apr 21 - Apr 22
Total with taxes and fees
This hotel features 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 free airport shuttle. Valet parking, a coffee shop, and a snack bar/deli are also offered.
Free airport shuttle
Pet friendly
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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 $792. 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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