Wiscasset Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $1,381, price is now CA $1,155 per person
CA $1,155
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,851 reviews)
Great location and spacious rooms. We brought our dog too! Loved grabbing a pre dinner drink and sitting by the cozy fireplace.

Reviewed on Nov 4, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was CA $2,111, price is now CA $1,578 per person
CA $1,578
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (419 reviews)

Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $1,762, price is now CA $1,475 per person
CA $1,475
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (342 reviews)

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $2,207, price is now CA $1,934 per person
CA $1,934
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (199 reviews)

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was CA $1,353, price is now CA $1,188 per person
CA $1,188
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,780 reviews)
Staff at the reception was not very warm and friendly at both check in and check out. However the valet staff and lounge staff were very kind and hospitable.

Reviewed on Nov 4, 2026

Ready to book your vacation to Wiscasset?

 

Choose your dates

Wiscasset Hotel Deals

Waterfront Retreat on Westport Island | Sunrooms, Fire pit & Water Views

Waterfront Retreat on Westport Island | Sunrooms, Fire pit & Water Views

Wiscasset ME
10/10 Exceptional! (1 review)
"Very comfortable and well outfitted place. More updated than many Maine properties. Well provisioned especially with coffee and coffee related stuff. Nice views, especially from the two water-view sunrooms. Even though the weather was chilly, there were space heaters that made those rooms comfortable ..."

Reviewed on Oct 26, 2026

Get rates
Waterfront Retreat on Westport Island | Sunrooms, Fire pit & Water Views
The Brunswick Hotel

The Brunswick Hotel

3 out of 5
4 Noble St Brunswick ME
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Nov 16 to Nov 17
CA $168
CA $183 total
Nov 16 - Nov 17
includes taxes & fees
The Brunswick Hotel
Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

2.5 out of 5
65 Whitten Rd Augusta ME
Fully refundable
The price is CA $188 per night from Nov 29 to Nov 30
CA $188
CA $204 total
Nov 29 - Nov 30
includes taxes & fees
Maine Evergreen Hotel, an Ascend Collection Hotel
See all 1,850 properties in Wiscasset
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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.
See properties

What to do in Wiscasset

Boothbay Harbor: Boos and Brews Walking Ghost Tour

Boothbay Harbor: Boos and Brews Walking Ghost Tour

CA $47
per adult
Boothbay Harbor: Boos and Brews Walking Ghost Tour
Portland Underground Railroad Self Guided Audio Walking Tour

Portland Underground Railroad Self Guided Audio Walking Tour

CA $14
per adult
Portland Underground Railroad Self Guided Audio Walking Tour
Have a brew with your boo at the Footbridge Brewery!

Boos and Brews Walking Ghost Tour of Boothbay Harbor

CA $47
per adult
100% of travellers recommend
Boos and Brews Walking Ghost Tour of Boothbay Harbor
See all activities in Wiscasset

Frequently asked questions

How much does a Wiscasset vacation package cost?
Offering excellent value package deals from CA $1,155 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?

  1. Pick your travel dates: The things you'd like to do in Wiscasset and your preferred season will help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.