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South Portland Vacation Packages

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South Portland Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Garrison Hotel & Suites Dover-Portsmouth, Ascend Hotel Collection

Garrison Hotel & Suites Dover-Portsmouth, Ascend Hotel Collection

2.5 out of 5
per person
Apr 13 - Apr 19
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Book a stay at this business-friendly hotel in Dover. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodman Institute and The Children's Museum of New Hampshire are located nearby.
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Save 100% on your flight
per person
Apr 13 - Apr 19
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Boston. Enjoy 2 bars/lounges, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Flynn Cruiseport Boston and New England Aquarium are located nearby.
The Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
per person
Apr 13 - Apr 19
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Portsmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Market Square and Rundlet-May House are located nearby.
Guest House Suites

Guest House Suites

2 out of 5
per person
Apr 13 - Apr 19
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Stay at this hotel in Salisbury. Enjoy free WiFi, free parking, and an in-room coffeemaker. Popular attractions Seabrook Beach and Parker River National Wildlife Refuge are located nearby.
TownePlace Suites Boston Logan Airport/Chelsea

TownePlace Suites Boston Logan Airport/Chelsea

3 out of 5
per person
Apr 13 - Apr 19
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Chelsea. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

3 out of 5
per person
Apr 13 - Apr 19
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Stay at this 3-star boutique hotel in Boston. Enjoy free bicycles on site, a 24-hour front desk, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Sheraton Boston, a Marriott Hotel

Sheraton Boston, a Marriott Hotel

4 out of 5
per person
Apr 13 - Apr 19
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Book a stay at this eco-certified hotel in Boston. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
per person
May 2 - May 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Boston Common are located nearby.

South Portland Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
River View Resort

River View Resort

2.5 out of 5
Save 100% on your flight
per person
May 4 - May 7
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
The Wolfeboro Inn

The Wolfeboro Inn

3.5 out of 5
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
The Cove At Salem

The Cove At Salem

3 out of 5
Save 100% on your flight
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)

South Portland Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Boston - Woburn, an IHG Hotel

Crowne Plaza Boston - Woburn, an IHG Hotel

3.5 out of 5
per person
Apr 13 - Apr 19
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
per person
Apr 13 - Apr 19
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Hyatt Place Boston/Medford

Hyatt Place Boston/Medford

3 out of 5
per person
Apr 13 - Apr 19
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Seaport District
Save 100% on your flight
per person
Apr 13 - Apr 19
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)

Top Flight Deals

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

Frontier Airlines
Wed, Mar 12 - Wed, Mar 26
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$89 Roundtrip, found 6 days ago
$89
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Mar 12 from Tampa Intl. to Portland Intl. Jetport, returning Wed, Mar 26, priced at $89 found 6 days ago
Breeze Airways
Fri, Apr 4 - Mon, Apr 7
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$108 Roundtrip, found 6 days ago
$108
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Apr 4 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Apr 7, priced at $108 found 6 days ago
Frontier Airlines
Sat, Apr 19 - Mon, Apr 28
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$108 Roundtrip, found 5 days ago
$108
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Apr 19 from Orlando Intl. to Portland Intl. Jetport, returning Mon, Apr 28, priced at $108 found 5 days ago
JetBlue Airways
Mon, Mar 31 - Tue, Apr 1
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Mar 31 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Tue, Apr 1, priced at $127 found 1 day ago