Search Deals on
Bailey Island Vacation Packages

Build your package with 2 more options

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 $682, price is now $483 per person
$483
per person
Feb 18 - Feb 21
found 12 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Hilton Garden Inn Freeport Downtown

Hilton Garden Inn Freeport Downtown

3 out of 5
Price was $736, price is now $547 per person
$547
per person
Feb 18 - Feb 21
found 12 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this business-friendly hotel in Freeport. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions LL Bean Flagship Store and Freeport Historical Society are located nearby.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,558, price is now $1,165 per person
$1,165
per person
Jan 29 - Feb 2
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this luxury resort in Cape Neddick. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Perkins Cove and Marginal Way are located nearby.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Price was $789, price is now $609 per person
$609
per person
Jan 29 - Feb 2
found 24 hours 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.
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
Price was $717, price is now $571 per person
$571
per person
Feb 18 - Feb 21
found 12 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hadlock Field and Home of the Maine Celtics are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $733, price is now $592 per person
$592
per person
Jan 29 - Feb 2
found 24 hours 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.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $782, price is now $644 per person
$644
per person
Jan 29 - Feb 2
found 24 hours 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.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $921, price is now $759 per person
$759
per person
Jan 29 - Feb 2
found 24 hours 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.

Bailey Island Vacation Packages 3-4 Night Stays

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

Casco Bay Inn

2 out of 5
Price was $682, price is now $483 per person
$483
per person
Feb 18 - Feb 21
found 12 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Hilton Garden Inn Freeport Downtown

Hilton Garden Inn Freeport Downtown

3 out of 5
Price was $736, price is now $547 per person
$547
per person
Feb 18 - Feb 21
found 12 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $1,558, price is now $1,165 per person
$1,165
per person
Jan 29 - Feb 2
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $789, price is now $609 per person
$609
per person
Jan 29 - Feb 2
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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
Price was $579, price is now $430 per person
$430
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $705, price is now $477 per person
$477
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was $631, price is now $471 per person
$471
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $900, price is now $690 per person
$690
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)

Top Flight Deals

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

Breeze Airways
Mon, Jan 5 - Fri, Jan 9
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$170 Roundtrip, found 2 days ago
$170
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Mon, Jan 5 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Fri, Jan 9, priced at $170 found 2 days ago
Breeze Airways
Mon, Dec 29 - Wed, Jan 7
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Dec 29 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Jan 7, priced at $173 found 1 day ago
Bargain Flight
Tue, Jan 20 - Sat, Jan 24
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$184 Roundtrip, found 2 days ago
$184
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Tue, Jan 20 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sat, Jan 24, priced at $184 found 2 days ago
Breeze Airways
Fri, Feb 6 - Sun, Feb 8
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$251 Roundtrip, found 1 day ago
$251
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Feb 6 from Tampa Intl. to Portland Intl. Jetport, returning Sun, Feb 8, priced at $251 found 1 day ago