Wiscasset Vacation Packages
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Your Wiscasset Vacation
Reserve a Wiscasset vacation package and you can prioritize what matters — having some fun. There's no more planning headaches, just a lot more free time to experience the delights of this fascinating city, such as its rich history and coastal scenery. A trip to Wiscasset is a wonderful opportunity to sightsee. Check out renowned attractions like Lincoln County Jail Museum, Wiscasset, Waterville and Farmington Railway Museum and Little Point. Your perfect Wiscasset vacation is clicks away. Browse hotels, flights and more on Expedia for a trip that's tailored just for you.
Top Wiscasset Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 121 Middle Street
Downtown Portland
CA $1,619
per person
Nov 27 - Nov 30
found 22 hours ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
9.6/10 Exceptional! (400 reviews)
We loved staying at the Docent's Collection at 121 Middle Street. Great staff, great location and great studio. Bed was excellent and the bathroom was large with very nice shower. Loved staying there.
Reviewed on Oct 24, 2026
Inn By The Sea
CA $2,402
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
9.6/10 Exceptional! (342 reviews)
Great pet friendly resort that allowed the dog to remain in the room while dining in the restaurant. Pet was allowed in the lounge area where they offered the same dining room menu, if you wanted to bring you pet along
. Pet treats and food and water dishes already in place in the room.
Reviewed on Oct 22, 2026
Pond And Pine
CA $2,571
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
10/10 Exceptional! (5 reviews)
This glamping cabin was everything we hoped for and more! Cozy, romantic, and clean. The outdoor kitchen had all the essentials, the private hot tub was amazing, and watching the sunrise and sunset from the deck felt magical. We roasted marshmallows by the fire pit overlooking the water and felt totally tucked away from the world yet the grocery store and casino were just minutes away. The perfect mix of peace, fun, and luxury. Can’t wait to come back!
Reviewed on Oct 27, 2025
Ready to book your vacation to Wiscasset?
Wiscasset Hotel Deals
Waterfront Retreat on Westport Island | Sunrooms, Fire pit & Water Views
Wiscasset ME
The Brunswick Hotel
4 Noble St Brunswick ME
Fully refundableReserve now, pay when you stay
CA $169
CA $184 total
Nov 9 - Nov 10
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"All was amazing looking forward to staying again"
Reviewed on Oct 21, 2026
Maine Evergreen Hotel, an Ascend Collection Hotel
65 Whitten Rd Augusta ME
Fully refundable
CA $182
CA $198 total
Nov 22 - Nov 23
includes taxes & fees
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.
Stay near popular Wiscasset attractions
Brooks Point
10.0/10 (2 reviews)
Commune with nature and explore the great outdoors at Brooks Point during your travels in Westport.
Wiscasset Historic District
You can learn about the history of Wiscasset when you stop by Wiscasset Historic District. Wander the forest and waterfront while you're in the area.
Castle Tucker
10.0/10 (2 reviews)
You can spend an afternoon exploring the galleries in Castle Tucker in Wiscasset. While you're in the area, stroll along the waterfront.
Monkey C Monkey Do
6.0/10 (2 reviews)
Enjoy a trip to Monkey C Monkey Do and popular activities like boating in Wiscasset. While you're in the area, stroll along the waterfront.
Lincoln County Jail Museum
8.8/10 (3 reviews)
You can spend an afternoon browsing the exhibits at Lincoln County Jail Museum during your travels in Wiscasset. While you're in the area, stroll along the waterfront.
What to do in Wiscasset
Boothbay Harbor: Boos and Brews Walking Ghost Tour
CA $47
per adult
Spooks and Spirits Walking Ghost Tour of Boothbay Harbor
CA $47
per adult
90-Minute Ghost Walking Tour in Boothbay Harbor
CA $42
per adult
100% of travellers recommend
Frequently asked questions
How much does a Wiscasset vacation package cost?
Offering excellent value package deals from CA $1,619 on Expedia, you'll be pleasantly surprised at how much a vacation to Wiscasset costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Wiscasset?
To score cheap Wiscasset vacation packages, organize your trip outside of peak periods such as school holidays. You'll typically find lower prices and better availability when it's less busy.
How many days is enough for Wiscasset?
Typically, a handful of days is enough to tick off the top attractions during your Wiscasset vacation. However, if you prefer to have some time to relax or take day tours, think about extending your trip.
How to find the best Wiscasset package deals?
Begin your search for a Wiscasset package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Wiscasset package deal straight away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Wiscasset escape underway.
Is it cheaper to book a Wiscasset vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Wiscasset vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Wiscasset?
Score incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Wiscasset adventure.
How to plan a trip to Wiscasset?
- Pick your travel dates: The things you'd like to do in Wiscasset and your preferred season will help you decide when to travel.
- Set your budget: Factor in costs like flights, transportation and food when calculating how much to set aside for your trip to Wiscasset. Then, select a property that matches your budget, whether that's an affordable option or a swankier getaway.
- Determine how many days away: Start by compiling a list of the activities and attractions you'd like to get to in Wiscasset. Then, estimate how long you'll need for each, including any travel time.
- Combine your accommodations and airfare: After you've settled on your trip dates and duration, lock in the perfect Wiscasset vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
