Search Deals onChebeague Island Vacation Packages
Chebeague Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites
Price was $1,148, price is now $821 per person
$821
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Moody Beach are located nearby.
Evalina Hotel
Save 100% on your flight
Price was $2,735, price is now $1,747 per person
$1,747
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Cross Insurance Arena and Casco Bay Lines Ferry Terminal are located nearby.
The accommodations were perfect for a family of 4. The 2 bedroom/2 bath was very spacious, very well laid out and in an excellent location. We really enjoyed our stay!
Reviewed on Jul 28, 2026
The Meadowmere Resort
Save 100% on your flight
Price was $1,481, price is now $979 per person
$979
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
Chebeague Island Inn
Save 100% on your flight
Price was $1,287, price is now $869 per person
$869
per person
Sep 1 - Sep 5
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Book a stay at this beach hotel in Chebeague Island. Enjoy free WiFi, breakfast (surcharge), and a free ferry terminal shuttle. Popular attractions Little John Island Preserve and Winslow Memorial Park are located nearby.
Blind Tiger Portland - Danforth Street.
Save 100% on your flight
Price was $2,783, price is now $1,908 per person
$1,908
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions State Theatre and Cross Insurance Arena are located nearby.
This hotel is amazing. The rooms, beds, and all the details are so incredible. I wish I could have stayed longer. Check in was a breeze as well. You can tell they take a lot of care and thought into the property. I will definitely be back
Reviewed on Jul 25, 2026
Inn at Diamond Cove
Price was $1,309, price is now $944 per person
$944
per person
Sep 12 - Sep 16
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, 2 restaurants, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Casco Bay Lines Ferry Terminal and Cross Insurance Arena are located nearby.
Inn By The Sea
Save 100% on your flight
Price was $2,241, price is now $1,675 per person
$1,675
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Higgins Beach and Portland Head Light are located nearby.
Ocean Gate Inn
Save 100% on your flight
Price was $1,471, price is now $1,107 per person
$1,107
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Portland (PWM)
Stay at this hotel in Southport. Enjoy free breakfast, an outdoor pool, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular attractions Coastal Maine Botanical Gardens and Juniper Point are located nearby.
Chebeague Island Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chebeague Island Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Aug 26 - Sat, Sep 5
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$170 Roundtrip, found 4 days ago
$170
Roundtrip
found 4 days ago
Mon, Aug 17 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$198 Roundtrip, found 4 days ago
$198
Roundtrip
found 4 days ago
Tue, Sep 8 - Sat, Sep 12
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$204 Roundtrip, found 4 days ago
$204
Roundtrip
found 4 days ago
Tue, Aug 25 - Wed, Sep 9
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$216 Roundtrip, found 4 days ago
$216
Roundtrip
found 4 days ago
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