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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.
Nautical Mile

Nautical Mile

2.5 out of 5
Price was $744, price is now $616 per person
$616
per person
Dec 18 - Dec 21
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this aparthotel in Wells. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Wells Beach and Moody Beach are located nearby.
I've stayed at the Nautical Mile many times! The rooms are perfect for a get-away! The pool is always ready to cool off in and the people, both working at the Nautical Mile and guests are very friendly.

Reviewed on Sep 8, 2026

84 Main

84 Main

4 out of 5
Price was $1,122, price is now $915 per person
$915
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this condo in Kennebunk. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Dock Square and Wells Beach are located nearby.
The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.

Reviewed on Jul 17, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $831, price is now $682 per person
$682
per person
Dec 18 - Dec 21
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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 Marginal Way and Ogunquit Beach are located nearby.

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $1,011, price is now $842 per person
$842
per person
Nov 23 - Nov 28
found 11 hours ago
Roundtrip 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.
Excellent, well-situated hotel. Front desk personnel were helpful and courteous. Sean and Simone were so kind in finding us the perfect room to suit our needs. Olivia at the bar in the evening was professional; we enjoyed our conversations with her. Great coffee-nook with perfect additions for a continental breakfast. Thanks to all who helped make our stay so enjoyable.

Reviewed on Oct 20, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $1,561, price is now $1,314 per person
$1,314
per person
Nov 23 - Nov 28
found 11 hours ago
Roundtrip 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.

Cape Arundel Inn and Resort

Cape Arundel Inn and Resort

3 out of 5
Price was $1,356, price is now $1,147 per person
$1,147
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this guesthouse in Kennebunkport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Dock Square and Wells Beach are located nearby.
Ocean view was amazing and check in was painless and very nice with a glass Of Prosecco given to Us!

Reviewed on Oct 19, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $2,416, price is now $2,074 per person
$2,074
per person
Nov 23 - Nov 28
just found
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 breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,199, price is now $1,045 per person
$1,045
per person
Nov 23 - Nov 28
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dock Square and Wells Beach are located nearby.
The staff was very friendly and helpful. The room was clean and nice, while still maintaining an old charm. The location was great.

Reviewed on Oct 19, 2026

Chebeague Island Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Nautical Mile

Nautical Mile

2.5 out of 5
Price was $744, price is now $616 per person
$616
per person
Dec 18 - Dec 21
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $831, price is now $682 per person
$682
per person
Dec 18 - Dec 21
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,072, price is now $902 per person
$902
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
Cape Arundel Inn and Resort

Cape Arundel Inn and Resort

3 out of 5
Price was $1,356, price is now $1,147 per person
$1,147
per person
Dec 24 - Dec 27
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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $1,011, price is now $842 per person
$842
per person
Nov 23 - Nov 28
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
84 Main

84 Main

4 out of 5
Price was $1,122, price is now $915 per person
$915
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,940, price is now $1,610 per person
$1,610
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,742, price is now $1,447 per person
$1,447
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip 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
Thu, Nov 12 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$185 Roundtrip, found 1 day ago
$185
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Nov 12 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at $185 found 1 day ago
Breeze Airways
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$192 Roundtrip, found 4 hours ago
$192
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $192 found 4 hours ago
Delta
Sat, Dec 5 - Tue, Dec 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$207 Roundtrip, found 1 hour ago
$207
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Dec 5 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Tue, Dec 8, priced at $207 found 1 hour ago
Delta
Tue, Nov 10 - Wed, Nov 18
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$207 Roundtrip, found 1 hour ago
$207
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Nov 10 from Tampa Intl. to Portland Intl. Jetport, returning Wed, Nov 18, priced at $207 found 1 hour ago