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Bailey Island Vacation Packages

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Bailey Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Casco Bay Inn

Casco Bay Inn

2 out of 5
Price was $571, price is now $474 per person
$474
per person
Feb 24 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LL Bean Flagship Store and Eartha are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $1,059, price is now $740 per person
$740
per person
Apr 14 - Apr 19
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 Fore Street Gallery are located nearby.
84 Main

84 Main

4 out of 5
Save 100% on your flight
Price was $848, price is now $600 per person
$600
per person
Feb 24 - Mar 3
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 Kennebunk Free Library are located nearby.
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $1,055, price is now $800 per person
$800
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Fort Preble and Portland Harbor Museum are located nearby.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Price was $1,164, price is now $886 per person
$886
per person
Apr 14 - Apr 19
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 Maine Sports Hall of Fame and Cathedral of the Immaculate Conception are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,413, price is now $1,150 per person
$1,150
per person
Apr 14 - Apr 19
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 a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,245, price is now $1,030 per person
$1,030
per person
Apr 14 - Apr 19
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 concierge services. Popular attractions Victoria Mansion and Portland Club are located nearby.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $959, price is now $798 per person
$798
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions N.W. Barrett Gallery and Fore Street Gallery are located nearby.

Bailey Island Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
84 Main

84 Main

4 out of 5
Price was $617, price is now $517 per person
$517
per person
Mar 7 - Mar 10
just found
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $922, price is now $706 per person
$706
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $1,078, price is now $917 per person
$917
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Price was $1,394, price is now $1,202 per person
$1,202
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)

Bailey 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
Save 100% on your flight
Price was $941, price is now $563 per person
$563
per person
Mar 4 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
Price was $1,025, price is now $656 per person
$656
per person
Mar 4 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $958, price is now $664 per person
$664
per person
Mar 4 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
84 Main

84 Main

4 out of 5
Save 100% on your flight
Price was $848, price is now $600 per person
$600
per person
Feb 24 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)

Top Flight Deals

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

American Airlines
Wed, May 27 - Thu, May 28
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$205 Roundtrip, found 1 day ago
$205
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Thu, May 28, priced at $205 found 1 day ago
JetBlue Airways
Wed, May 27 - Wed, Jun 3
ATL
Hartsfield-Jackson Atlanta Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, May 27 from Hartsfield-Jackson Atlanta Intl. to Portland Intl. Jetport, returning Wed, Jun 3, priced at $217 found 1 day ago
JetBlue Airways
Mon, May 18 - Wed, May 27
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$220 Roundtrip, found 2 days ago
$220
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Mon, May 18 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, May 27, priced at $220 found 2 days ago
Delta
Thu, Apr 9 - Mon, Apr 13
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$237 Roundtrip, found 12 hours ago
$237
Roundtrip
found 12 hours ago
Select Delta flight, departing Thu, Apr 9 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Mon, Apr 13, priced at $237 found 12 hours ago