Freeport Vacations
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Freeport Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Old Orchard Beach Inn
$739
per person
Sep 21 - Sep 26
found 15 hours ago
Roundtrip non-stop flight included
Tulsa (TUL) to Portland (PWM)
Stay at this B&B in Old Orchard Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Palace Playland and Old Orchard Beach are located nearby.
This review has been rejected several times, perhaps because it was too negative. Of the three properties I booked for this trip on different platforms, Old Orchard Beach Inn was the most disappointing. The room and bathroom needed a complete refresh. The furniture was old (not antique, poor reproductions and broken down). The bathroom was small and very dated. There was only one very small window and the room was dark. The lighting was terrible. Location was good. I only interacted with one staff person, who booked me in. The breakfast was acceptable--eggs, sausage and potatoes kept warm on a flame, and a fairly good variety of other breakfast foods. The breakfast is served two doors away, a short walk but it was pouring rain that morning. Parking was fine. This property was below my expectations for Hotels.com, compared with other properties I have booked on your platform. My rating for this property is significantly lower than the one on your website.
Reviewed on Aug 9, 2026
Portland Harbor Hotel
Downtown Portland
$1,453
per person
Sep 21 - Sep 26
found 15 hours ago
Roundtrip non-stop flight included
Tulsa (TUL) 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 Casco Bay Lines Ferry Terminal are located nearby.
We had a shower that leaked all the way out to the foyer. We called and reported it. They sent a repair person. They caulked around the edge which helped but didn’t fix the whole problem. It still leaked, just not as bad. No one followed up to see if it was fixed. They have a pantry on each floor with fruit infused water snacks, fresh fruit, cookies, canned sparkling water and ice for free. But it was mostly depleted most of the time we were there. There was a sign advertising live music at the front of the hotel. But when we asked where it was, the hotel attendant said they were not having live music after all. No one went to take the sign down. It was still there the next day. We checked out. Hope the musician showed up that night.
Reviewed on Aug 7, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
$1,675
per person
Sep 21 - Sep 26
found 15 hours ago
Roundtrip non-stop flight included
Tulsa (TUL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Casco Bay Lines Ferry Terminal and Cross Insurance Arena are located nearby.
Fantastic and always accommodating staff!
Reviewed on Aug 7, 2026
The Weldon Hotel
Downtown Portland
$2,077
per person
Sep 21 - Sep 26
found 15 hours ago
Roundtrip non-stop flight included
Tulsa (TUL) 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 Cross Insurance Arena and State Theatre are located nearby.
The rooms were clean and spacious. The location was very convenient to the Old port. Parking was right across the street. The only drawback was a mechanical noise that we believe originated from the building next door. This noise made it sometimes difficult to sleep. Having a kitchen and laundry were helpful.
Reviewed on Aug 4, 2026
The Docent's Collection at 178 Middle Street
Downtown Portland
$2,282
per person
Sep 21 - Sep 26
found 15 hours ago
Roundtrip non-stop flight included
Tulsa (TUL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Cross Insurance Arena and Casco Bay Lines Ferry Terminal are located nearby.
Evalina Hotel
Downtown Portland
$2,289
per person
Sep 21 - Sep 26
found 15 hours ago
Roundtrip non-stop flight included
Tulsa (TUL) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Maine Mall and Cross Insurance Arena are located nearby.
It was our first time visiting Portland, and the Evalina exceeded our expectations. The location is perfect, right on Commercial Street, with plenty of restaurants and shops nearby. The ferry and cruise ports are also just a 5–10 minute walk away, making it easy to visit the different islands.
The suite was comfortable and thoughtfully equipped with everything we could need, including an umbrella for rainy days, coffee and a French press, tea, a washer and dryer, and so much more. Communication was excellent throughout our stay as well.
We truly enjoyed our visit, and the next time we’re in Portland, the Evalina will be our first choice!
Reviewed on Aug 8, 2026
Freeport Vacation Packages
Hoping to save both time and money on your next trip to Freeport? The AARP Travel Center Powered by Expedia® can help you do both. We're here to book everything you'll need to make your Freeport trip one to remember. Our Travel Center is a one-stop shop where you can put together the best Freeport vacation package for you. AARP Travel Center has an incredible selection of accommodations and flight, as well as Freeport endeavors to choose from.
Hotels in Freeport
You can choose from around 1932 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Freeport hot spots, we have plenty of options available.
From Freeport hotels with multiple pools and on-site restaurants, to boutique accommodations that add all the thoughtful amenities, you'll get a hotel here that will make your trip one to remember. With AARP Travel Center's Freeport hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.
Things to do in Freeport
Freeport is the perfect spot when you need to get away from it all. With only around 8,316 people living here year-round, this cozy town is good for a quite vacation. If you want to take walk through the past, then you are in luck as Freeport has a rich historic district.
The AARP Travel Center "Things to Do" page has more great activities that you can book.
Book Together and Save
With so much to see and do in Freeport, you'll be wanting to plan your outings, not spending time to finding the cheapest hotel. The AARP Travel Center Powered by Expedia® allows you to quickly reserve all you want, and save money doing it. You can coordinate your entire holiday, including things to do in Freeport from just one site. The hardest packing you'll have to do is for your suitcase. Bundle now and save!
Top Hotel Deals
The Freeport Hotel, an Ascend Collection Hotel
506 Us Route 1 Freeport ME
Book a stay at this business-friendly motel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Holiday Inn Express Hotel & Suites Freeport by IHG
450 U.S. Route 1 Freeport ME
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
Best Western Freeport Inn
31 US Route 1 Freeport ME
Stay at this hotel in Freeport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
The Harraseeket Inn & Event House Freeport Downtown
162 Main St Freeport ME
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Econo Lodge Freeport - Brunswick Area
537 Route 1 South Freeport ME
Book a stay at this business-friendly motel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
SpringHill Suites by Marriott Freeport Brunswick
500 US-1 Freeport ME
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Hilton Garden Inn Freeport Downtown
5 Park St Freeport ME
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 ...
Hampton Inn Freeport/Brunswick
194 Lower Main St Freeport ME
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Orchard House: Inn & Cafe
1 Grey Barn Way Freeport ME
Stay at this B&B in Freeport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LL Bean Flagship Store and Mast Landing Sanctuary are located ...
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's ...
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Portland Regency Hotel & Spa
20 Milk Street Portland ME
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 ...
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
Comfort Inn South Portland Airport
90 Maine Mall Rd South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Aug 31 - Tue, Sep 1
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$202
Roundtrip
found 21 hours ago
Thu, Oct 8 - Fri, Oct 16
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$237
Roundtrip
found 6 days ago
Wed, Aug 26 - Wed, Sep 9
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$247
Roundtrip
found 1 day ago
Mon, Aug 31 - Tue, Sep 1
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$248
Roundtrip
found 21 hours ago
Mon, Aug 31 - Tue, Sep 1
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$267
Roundtrip
found 21 hours ago
Best points of interest in Freeport
- LL Bean Flagship Store Vacations
- Desert of Maine Vacations
- Wolfe's Neck Woods State Park Vacations
- Winslow Memorial Park Vacations
- Wolfe's Neck Farm Vacations
- Harrington House Vacations
- Freeport Historical Society Vacations
- Bradbury Mountain State Park Vacations
- Mast Landing Sanctuary Vacations
- Wilbur's of Maine Chocolate Confections Vacations
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All accommodation types in Freeport
More Types of Hotels
- Hotels with Air Conditioning in Freeport
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- Smoke Free Hotels in Freeport
- Hotels with a Pool in Freeport
- Cheap Hotels in Freeport
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- Hotel with a Concierge in Freeport
- Hotels with Hot Tubs in Freeport
- Resorts & Hotels with Spas in Freeport
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- Pet-friendly Hotels in Freeport
- Hotels with Balconies in Freeport
- Hotels with Fireplaces in Freeport
- Hotels with smoking rooms in Freeport
- Hotels with Tennis Courts in Freeport
- Hotels with Early Check-in in Freeport