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Chebeague Island Vacation Packages

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Chebeague Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $852, price is now $677 per person
$677
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
Price was $1,125, price is now $838 per person
$838
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Great location and cool property. No TV though.

Reviewed on Sep 28, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Price was $1,230, price is now $920 per person
$920
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop 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 Maine Mall are located nearby.
Better than expected. This new property was in a great location. Easy to walk to restaurants and shopping. Comfortable bed, nice bathroom and a sitting area with sofa, chair and tv. I was a little concerned because we could hear music from a nearby bar, but everything stopped by 10 o’clock. Would return.

Reviewed on Sep 25, 2026

The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Price was $1,241, price is now $939 per person
$939
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $1,156, price is now $884 per person
$884
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.

The Kendall Inn

The Kendall Inn

3.5 out of 5
Price was $1,033, price is now $806 per person
$806
per person
Dec 3 - Dec 8
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Freeport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LL Bean Flagship Store and Freeport Historical Society are located nearby.
We had a wonderful stay! The innkeepers - Stephanie, Keith, and Matthew were great! Loved the breakfast choices! We enjoyed the front porch as well.

Reviewed on Sep 21, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,221, price is now $966 per person
$966
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Place was charming and quirky. Very comfortable and well located.

Reviewed on Sep 18, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,134, price is now $898 per person
$898
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop 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 breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
Staff and food were both wonderful. We would definitely stay again.

Reviewed on Sep 28, 2026

Chebeague Island Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $1,125, price is now $838 per person
$838
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was $1,230, price is now $920 per person
$920
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Downtown Portland
Price was $1,241, price is now $939 per person
$939
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
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 $1,156, price is now $884 per person
$884
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)

Chebeague Island Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Kendall Inn

The Kendall Inn

3.5 out of 5
Price was $1,108, price is now $832 per person
$832
per person
Oct 30 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $1,308, price is now $932 per person
$932
per person
Dec 3 - Dec 8
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Downtown Portland
Price was $1,428, price is now $1,039 per person
$1,039
per person
Dec 3 - Dec 8
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
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 $1,322, price is now $973 per person
$973
per person
Dec 3 - Dec 8
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Sat, Nov 7 - Sat, Nov 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$144 Roundtrip, found 2 days ago
$144
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Nov 7 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Nov 14, priced at $144 found 2 days ago
Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$187 Roundtrip, just found
$187
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $187 just found
Breeze Airways
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$203 Roundtrip, found 12 hours ago
$203
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $203 found 12 hours ago
Bargain Flight
Tue, Oct 6 - Fri, Oct 16
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$227 Roundtrip, found 18 hours ago
$227
Roundtrip
found 18 hours ago
Select Bargain Flight flight, departing Tue, Oct 6 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Fri, Oct 16, priced at $227 found 18 hours ago