Search Deals onSouth Portland Vacation Packages
South Portland Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites
Price was $780, price is now $551 per person
$551
per person
May 7 - May 11
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
The Cove at Yarmouth by Westgate Resorts
Save 100% on your flight
Price was $979, price is now $592 per person
$592
per person
May 29 - Jun 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this spa aparthotel in West Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Hyannis Harbor and Mayflower Beach are located nearby.
Red Roof Inn PLUS+ Boston - Woburn/ Burlington
Save 100% on your flight
Price was $864, price is now $577 per person
$577
per person
Jun 9 - Jun 13
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Woburn. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Burlington Mall and MarketStreet Lynnfield are located nearby.
The Langham, Boston
Save 100% on your flight
Price was $1,461, price is now $1,015 per person
$1,015
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions New England Aquarium and Boston Common are located nearby.
Portland Harbor Hotel
Save 100% on your flight
Price was $1,643, price is now $1,163 per person
$1,163
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip flight included
Nashville (BNA) 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 Maine Mall and Cross Insurance Arena are located nearby.
The Inn at Hastings Park, Relais & Chateaux - Boston
Price was $1,291, price is now $914 per person
$914
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
Book a stay at this luxury hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Lexington Battle Green and Burlington Mall are located nearby.
Boston Harbor Hotel
Save 100% on your flight
Price was $3,411, price is now $2,450 per person
$2,450
per person
Jun 9 - Jun 13
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this 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.
Luxury 2BR near Cambridge
Save 100% on your flight
Price was $2,395, price is now $1,725 per person
$1,725
per person
Jun 11 - Jun 15
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
Stay at this apartment in Somerville. Enjoy free WiFi and air conditioning. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
South Portland Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
South Portland Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Aug 22 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$178 Roundtrip, found 3 hours ago
$178
Roundtrip
found 3 hours ago
Sat, May 23 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$195 Roundtrip, found 20 hours ago
$195
Roundtrip
found 20 hours ago
Wed, Apr 15 - Mon, Apr 27
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$230 Roundtrip, found 7 hours ago
$230
Roundtrip
found 7 hours ago
Tue, Jun 16 - Wed, Jun 17
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$262 Roundtrip, found 1 day ago
$262
Roundtrip
found 1 day ago
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