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 Cornish Inn

The Cornish Inn

3 out of 5
Price was CA $1,251, price is now CA $1,091 per person
CA $1,091
per person
Aug 5 - Aug 12
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
9.2/10 Wonderful! (59 reviews)
comfortable beds, clean room, nice having bar & restaurant in same building, would be helpful to have grab bar in the shower

Reviewed on Jun 10, 2026

USA Inn

USA Inn

2.5 out of 5
Price was CA $1,581, price is now CA $1,268 per person
CA $1,268
per person
Aug 5 - Aug 12
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
8/10 Very good! (797 reviews)
Everything was good room was nice but just didnt like the bathroom it was small. Cleaning staff keeped it clean & front desk was very nice..

Reviewed on Jul 1, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was CA $1,852, price is now CA $1,615 per person
CA $1,615
per person
Aug 27 - Aug 30
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,682 reviews)

The Majestic Regency Resort

The Majestic Regency Resort

2.5 out of 5
Moody
Price was CA $1,506, price is now CA $1,315 per person
CA $1,315
per person
Aug 5 - Aug 12
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
7/10 Good! (1,010 reviews)
Not the newest place but it served exactlywhat we needed

Reviewed on Jul 4, 2026

The Bethel Resort & Suites

The Bethel Resort & Suites

3 out of 5
Price was CA $1,415, price is now CA $1,244 per person
CA $1,244
per person
Aug 5 - Aug 12
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
7.8/10 Good! (400 reviews)
Staff was very pleasant and helpful. Property was nice but a bit tired……could use some upkeep. Gym was dirty and outdoor pool wasn’t really heated. For the price, I would have expected better.

Reviewed on Jun 22, 2026

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Wiscasset Hotel Deals

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

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

Westport ME
8.6/10 Excellent! (62 reviews)
"Everything was as expected. Would have been nice to be able to see out all the windows, as many of them have broken seals and are foggy. The view is spectacular, but couldn"t enjoy it from everywhere in the house. The location was perfect for us, as we like being secluded."

Reviewed on Oct 12, 2025

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

Ocean Gate Inn

3 out of 5
70 Ocean Gate Rd Southport ME
The price is CA $361 per night from Jul 6 to Jul 7
CA $361
CA $413 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Great location. Staff was very friendly and helpful. Breakfast was good! Very clean and nice size room."

Reviewed on Jul 4, 2026

Ocean Gate Inn
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue Boothbay Harbor ME
Fully refundableReserve now, pay when you stay
The price is CA $216 per night from Jul 6 to Jul 7
CA $216
CA $294 total
Jul 6 - Jul 7
includes taxes & fees
8/10 Very good! (1,002 reviews)
"The property was nice, the room was spacious and accommodating. The breakfast was good for a free continental breakfast wit crispy bacon each morning. The location was very convenient for Captain Fish’s cruises and Boothbay dining & shopping."

Reviewed on Jul 3, 2026

Flagship Inn and Suites
See all 1,922 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.
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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: Lighthouses & Islands Harbor Cruise

Boothbay: Lighthouses & Islands Harbor Cruise

CA $56
per adult
94% of travellers recommend
Boothbay: Lighthouses & Islands Harbor Cruise
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 Daytime Sailing Cruise

Boothbay Harbor: Schooner Apple Jack Daytime Sailing Cruise

CA $76
per adult
Boothbay Harbor: Schooner Apple Jack Daytime Sailing Cruise
See all activities in Wiscasset

Frequently asked questions

How much does a Wiscasset vacation package cost?
Offering excellent value package deals from CA $1,091 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.