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Casco Bay Islands Vacation Packages

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Casco Bay Islands Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
Price was $798, price is now $571 per person
$571
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Maine Jewish Museum and Maine Narrow Gauge Railroad Company and Museum are located nearby.
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,346, price is now $872 per person
$872
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Victoria Mansion and Charles Q. Clapp House are located nearby.
The Docent's Collection - Boyd Block

The Docent's Collection - Boyd Block

2 out of 5
Save 100% on your flight
Price was $1,311, price is now $870 per person
$870
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Popular attractions Fore Street Gallery and Maine Sports Hall of Fame are located nearby.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Save 100% on your flight
Price was $1,081, price is now $717 per person
$717
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $1,445, price is now $988 per person
$988
per person
Dec 22 - Dec 27
found 4 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Save 100% on your flight
Price was $901, price is now $631 per person
$631
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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
Save 100% on your flight
Price was $919, price is now $659 per person
$659
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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.
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,302, price is now $954 per person
$954
per person
Feb 8 - Feb 15
found 1 day ago
Roundtrip flight included
New York (JFK) 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.

Casco Bay Islands Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3 out of 5
Downtown Portland
Price was $621, price is now $498 per person
$498
per person
Jan 15 - Jan 18
found 9 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $1,128, price is now $874 per person
$874
per person
Dec 26 - Dec 29
found 21 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Admiral Peary Inn

Admiral Peary Inn

3 out of 5
Price was $1,031, price is now $829 per person
$829
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $1,116, price is now $946 per person
$946
per person
Dec 26 - Dec 29
found 21 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)

Casco Bay Islands Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
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 $1,081, price is now $717 per person
$717
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,346, price is now $872 per person
$872
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
The Docent's Collection - Boyd Block

The Docent's Collection - Boyd Block

2 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,311, price is now $870 per person
$870
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $1,445, price is now $988 per person
$988
per person
Dec 22 - Dec 27
found 4 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)

Top Flight Deals

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

United
Mon, Dec 15 - Mon, Dec 15
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$171 Roundtrip, found 2 days ago
$171
Roundtrip
found 2 days ago
Select United flight, departing Mon, Dec 15 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Mon, Dec 15, priced at $171 found 2 days ago
Breeze Airways
Mon, Dec 22 - Wed, Dec 31
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$178 Roundtrip, found 2 days ago
$178
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Mon, Dec 22 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 31, priced at $178 found 2 days ago
Bargain Flight
Mon, Jan 12 - Wed, Jan 21
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 Mon, Jan 12 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Jan 21, priced at $184 found 2 days ago
Breeze Airways
Fri, Jan 2 - Tue, Jan 6
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$192 Roundtrip, found 4 days ago
$192
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jan 2 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Tue, Jan 6, priced at $192 found 4 days ago