Search Deals onFreeport Vacation Packages
Freeport Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Meadowmere Resort
Save 100% on your flight
Price was $982, price is now $661 per person
$661
per person
Oct 13 - Oct 17
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
The staff was wonderful and the grounds are very nice and well-maintained. The HVAC left something to be desired. The unit was loud and not particularly effective.
Reviewed on Aug 21, 2026
The Weldon Hotel
Save 100% on your flight
Price was $1,668, price is now $1,135 per person
$1,135
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 Maine Mall and Cross Insurance Arena are located nearby.
We had a wonderful stay. Highly recommend!
Reviewed on Aug 19, 2026
Ogunquit River Inn & Suites
Save 100% on your flight
Price was $1,633, price is now $1,118 per person
$1,118
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Check in was too slow even for patrons who had fully paid for their rooms.
Reviewed on Aug 21, 2026
Blind Tiger Portland - Danforth Street.
Save 100% on your flight
Price was $1,448, price is now $1,025 per person
$1,025
per person
Sep 21 - Sep 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions State Theatre and Casco Bay Lines Ferry Terminal are located nearby.
This hotel is amazing. The rooms, beds, and all the details are so incredible. I wish I could have stayed longer. Check in was a breeze as well. You can tell they take a lot of care and thought into the property. I will definitely be back
Reviewed on Jul 25, 2026
Blind Tiger Portland – Carleton Street
Save 100% on your flight
Price was $1,518, price is now $1,092 per person
$1,092
per person
Sep 21 - Sep 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions State Theatre and Cross Insurance Arena are located nearby.
Evalina Hotel
Save 100% on your flight
Price was $2,077, price is now $1,495 per person
$1,495
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Thompson's Point and Portland Head Light are located nearby.
Great location! Fun space! Comfortable and clean!
Reviewed on Aug 17, 2026
Inn By The Sea
Save 100% on your flight
Price was $1,916, price is now $1,390 per person
$1,390
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Portland Head Light and Crescent Beach State Park are located nearby.
Lovely property. Very well maintained and taken care of. The option of pool or beach is a plus. Although we didn’t utilize the activities available each day.. it seemed very family friendly. Definitely will be back but hopefully reserve a bigger room or suite. Charming outdoor seating on the huge lawn but mostly in the sun. An indoor lobby with some comfy seating would be great.
Reviewed on Aug 13, 2026
Newagen Seaside Inn
Price was $1,394, price is now $1,018 per person
$1,018
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Book a stay at this family-friendly hotel in Southport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Coastal Maine Botanical Gardens and Southport Memorial Library are located nearby.
Fabulous setting
Beautiful grounds
Clean rooms
Comfortable beds
Delicious food
Great views
Friendly and polite staff
Reviewed on Aug 14, 2026
Freeport Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Freeport 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.
Sun, Sep 6 - Fri, Sep 11
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$207 Roundtrip, found 3 days ago
$207
Roundtrip
found 3 days ago
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$209 Roundtrip, found 1 hour ago
$209
Roundtrip
found 1 hour ago
Tue, Sep 1 - Wed, Sep 2
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$214 Roundtrip, found 1 day ago
$214
Roundtrip
found 1 day ago
Mon, Sep 21 - Wed, Sep 23
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$220 Roundtrip, found 6 hours ago
$220
Roundtrip
found 6 hours ago
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