Wiscasset Vacations
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Wiscasset 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 1 day 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 1 day 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.
The Docent's Collection at 121 Middle Street
Downtown Portland
$1,675
per person
Sep 21 - Sep 26
found 1 day 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.
Unexpectedly found The Docent's Collection on my trip wanting to spend an extra night. I was generously accommodated before my 4 pm check in time as I was already in the area. It is a beautiful loft style apartment/room that is spacious and very clean. Also within walking distance of a lot of the places I wanted to visit. I loved it so much and I would definitely be back soon.
Reviewed on Aug 9, 2026
The Weldon Hotel
Downtown Portland
$2,077
per person
Sep 21 - Sep 26
found 1 day 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 1 day 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 1 day 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
Wiscasset Vacation Packages
Trying to figure out a way to package your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® Wiscasset vacation packages can help. We're here to book everything you'll need to make your Wiscasset trip one to remember. With just a few clicks, you can choose the best Wiscasset vacation package for you. AARP Travel Center has a huge list of flights and hotels, as well as local activities to pick from.
Wiscasset Hotels
Our listings include lodgings that are close to all the Wiscasset points of interest, and others that are just outside the city center for a peaceful retreat.
From Wiscasset hotels with swimming pools and on-site restaurants, to boutique accommodations that add all the thoughtful amenities, you'll find a hotel here that will make your trip amazing. With AARP Travel Center's Wiscasset hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.
Things to do in Wiscasset
Wiscasset is the ideal town when you need to a break from it all. With only around 3,652 people living here year-round, this cozy town is great for a quite vacation.
If you are looking for more, then head over to our "Things to Do" page for more inspiration or to reserve an activity in Wiscasset.
Book Together and Save
With so much happening in Wiscasset, you'll be wanting to focus on your outings, not spending time to searching for the hotel with the lowest rate. AARP Travel Center allows you to quickly book everything you wish for, and save a little money doing it. You can coordinate your whole trip, including activities in Wiscasset from only one site. So what are you waiting for? Bundle now and save!
Top Hotel Deals
Flagship Inn and Suites
200 Townsend Avenue Boothbay Harbor ME
Stay at this hotel in Boothbay Harbor. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the pool in our reviews. Popular ...
Maine Evergreen Hotel, an Ascend Collection Hotel
65 Whitten Rd Augusta ME
Book a stay at this family-friendly hotel in Augusta. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Senator Inn & Spa
284 Western Ave Augusta ME
Book a stay at this spa hotel in Augusta. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. ...
Travelers Inn
130 Pleasant St Brunswick ME
Book a stay at this business-friendly motel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
The Brunswick Hotel
4 Noble St Brunswick ME
Book a stay at this business-friendly hotel in Brunswick. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
Best Western Plus Brunswick Bath
71 Gurnet Road Brunswick ME
Book a stay at this family-friendly hotel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Days Inn by Wyndham Brunswick Bath Area
224 Bath Rd Brunswick ME
Book a stay at this business-friendly motel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Moonlight Inn
215 Pleasant St Brunswick ME
Stay at this motel in Brunswick. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Spark by Hilton Brunswick
199 Pleasant St Brunswick ME
Book a stay at this business-friendly hotel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Oceanfront Studio w/ Private Dock in Harpswell!
Harpswell ME
Stay at this apartment in Harpswell. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Mitchell Field and Bailey Island Bridge ...
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 ...
Residence Inn Bath Brunswick Area
139 Richardson St. Bath ME
Book a stay at this business-friendly hotel in Bath. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the property ...
Topside Inn
60 McKown St Boothbay Harbor ME
Stay at this hotel in Boothbay Harbor. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Coastal Maine Botanical Gardens and Burnt Island ...
Ocean Gate Inn
70 Ocean Gate Rd Southport ME
Stay at this hotel in Southport. Enjoy free breakfast, an outdoor pool, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Days Inn by Wyndham Augusta
18 Edison Dr. Augusta ME
Stay at this motel in Augusta. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
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 1 day ago
Wed, Aug 26 - Wed, Sep 9
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$247
Roundtrip
found 2 days ago
Sun, Oct 4 - Fri, Oct 9
EWR
Newark Liberty Intl. Airport
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 1 day ago
Mon, Aug 31 - Tue, Sep 1
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$267
Roundtrip
found 1 day ago
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All accommodation types in Wiscasset
More Types of Hotels
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