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.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (177 reviews)
We had an amazing stay! What a gem of an experience - all of the staff was wonderful - Antonio at the lobby cafe was so kind and friendly and Kayla at concierge always went above and beyond!!

Reviewed on Jul. 20, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,008 reviews)
The oceanview was breathtaking, the morning sun was stunning

Reviewed on Jul. 22, 2025

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,338 reviews)
Charming and very welcoming staff. We were able to walk everywhere easily. Great location!

Reviewed on Jul. 23, 2025

Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
Downtown Portland
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Portland (PWM)
8.8/10 Excellent! (1,153 reviews)
Great location and wonderful customer service! Really quiet in the room so you can hear quite a bit outside, shower pressure wasn't great but bed was comfortable and room was clean. There was some construction going on that we weren't aware of but it wasn't a deal breaker. Love that they offer airport shuttle!

Reviewed on Jul. 22, 2025

Chebeague Island Inn

Chebeague Island Inn

4 out of 5
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (72 reviews)
Great place to go and relax for a few days.

Reviewed on Jul. 20, 2025

Ready to book your vacation to Wiscasset?

 

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Wiscasset Hotel Deals

WATERFRONT Retreat venue for up to 60 guests!… Weddings, Reunions, Meetings!……

WATERFRONT Retreat venue for up to 60 guests!… Weddings, Reunions, Meetings!……

Westport Island
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WATERFRONT Retreat venue for up to 60 guests!… Weddings, Reunions, Meetings!……
Elegant riverside retreat with breathtaking views and modern comforts

Elegant riverside retreat with breathtaking views and modern comforts

Wiscasset
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Elegant riverside retreat with breathtaking views and modern comforts
Unique oceanfront home with a deck, tons of natural light, & amazing views

Unique oceanfront home with a deck, tons of natural light, & amazing views

Wiscasset
8.4/10 Very Good! (37 reviews)
Great House
"We loved this property and had a great time staying here. It was clean and check in/check out were a breeze. Nothing better than a cup of coffee on the porch watching the wildlife on the water in the morning!"

Reviewed on Jun. 5, 2025

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Unique oceanfront home with a deck, tons of natural light, & amazing views
See all 1,779 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

Discover the most popular places to visit in Wiscasset

Castle Tucker

You can spend an afternoon exploring the galleries in Castle Tucker in Wiscasset. While you're in the area, stroll along the waterfront.

Castle Tucker

What to do in Wiscasset

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

CA $82
per adult
Schooner Applejack Sunset Sail Tour in Boothbay Harbor
Boothbay Harbor: Schooner Apple Jack Sunset Sailing Cruise

Boothbay Harbor: Schooner Apple Jack Sunset Sailing Cruise

CA $82
per adult
100% of travellers recommend
Boothbay Harbor: Schooner Apple Jack Sunset Sailing Cruise
Boothbay: Lighthouses & Islands Harbor Cruise

Boothbay: Lighthouses & Islands Harbor Cruise

CA $56
per adult
94% of travellers recommend
Boothbay: Lighthouses & Islands Harbor Cruise
See all activities in Wiscasset

Frequently asked questions

How much does a Wiscasset vacation package cost?
Offering excellent value package deals from CA $858 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.