Wiscasset Vacations from $386

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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.

The Latest Wiscasset vacation packages

Price found within the past 48 hours. Click for updated prices.
InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (341 reviews)
Clean comfortable rooms. Nice amenities, walking distance to the beach and restaurants. Short drive or shuttle to downtown area. We would return and recommend this place.

Reviewed on Aug 16, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (1,005 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!

Reviewed on Aug 9, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
This place was awesome! Loved the pantry on our floor to get snacks

Reviewed on Aug 15, 2025

Chebeague Island Inn

Chebeague Island Inn

4 out of 5
Save 100% on your flight
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
8.8/10 Excellent! (76 reviews)
Great place to go and relax for a few days.

Reviewed on Jul 20, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
per person
Sep 26 - Sep 29
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
Great stay! The food was amazing! Cute added touch doing s’mores every night, my kids loved that! Only thing I’ll say is - the lobby area where you checkin and restaurant could use a remodel. Overall lovely experience.

Reviewed on Aug 16, 2025

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Discover the most popular places to visit in Wiscasset

Lincoln County Jail Museum

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.

Lincoln County Jail Museum

Monkey C Monkey Do

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.

Monkey C Monkey Do

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

Artisanal Maine Cheese Tasting and Class in Wiscasset

Artisanal Maine Cheese Tasting and Class in Wiscasset

$15
per adult
Artisanal Maine Cheese Tasting and Class in Wiscasset
Maine Fermented Foods Tasting and Class in Wiscasset

Maine Fermented Foods Tasting and Class in Wiscasset

$15
per adult
Maine Fermented Foods Tasting and Class in Wiscasset
Schooner Applejack Sunset Sail Tour in Boothbay Harbor

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

$60
per adult
Schooner Applejack Sunset Sail Tour in Boothbay Harbor
See all activities in Wiscasset

Wiscasset Hotel Deals

Elegant riverside retreat with breathtaking views and modern comforts

Elegant riverside retreat with breathtaking views and modern comforts

Wiscasset
Get rates
Elegant riverside retreat with breathtaking views and modern comforts
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!……
Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.

Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.

Westport
9.8/10 Exceptional! (93 reviews)
"I cannot praise this property enough. Check-in was seamless and any questions we had were answered immediately. From the moment we stepped inside, we felt at home. Everything was spotless, warm and inviting. Although we didn’t actually cook meals, the kitchen was well equipped. The house was spacious ..."

Reviewed on Aug 12, 2025

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Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.
See all 1,762 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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Frequently asked questions

How much does a Wiscasset vacation package cost?
You'll find cheap prices from $386 on Expedia for your Wiscasset getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Wiscasset costs.
What are the cheapest months to go to Wiscasset?
You're likely to find reduced prices and greater availability in January, October and December. Take a look at our cheap Wiscasset vacation packages and you could get some great off-season discounts.
How many days is enough for Wiscasset?
Generally, a handful of days is enough to explore the major attractions during your Wiscasset vacation. However, if you prefer to have some time to relax or take day trips, consider extending your trip.
How to find the best Wiscasset package deals?
Landing a cheap Wiscasset package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most economical Wiscasset package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Wiscasset vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging hotels and flights separately. Better still, you can personalize your Wiscasset getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Wiscasset?
If you're considering an impromptu Wiscasset trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Wiscasset?

  1. Choose when to get away: Check your calendar and get packing. Your preferred time of year and the available activities will also help you decide when to vacation in Wiscasset.
  2. Budget wisely: Besides the price of your hotel, you'll need to factor in other expenses too. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that may arise during your trip to Wiscasset.
  3. Discover Wiscasset using our trip planning tool: Gain insights into the leading attractions and best hotels for your trip to Wiscasset. You can also save your favorite places, collaborate with friends and family and organize your plans in one place.
  4. Decide how long to go away for: Now that you're more familiar with Wiscasset, you can work out the perfect length of your vacation. Pull together a draft itinerary and give yourself enough time for all the things you want to do.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Wiscasset vacation package.
  6. Add on experiences and excursions: Have a look at our dedicated travel guide to find some incredible things to do in Wiscasset. Book tickets or make reservations before you go to save time and skip the hassle of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Wiscasset vacation packages?
Your Wiscasset getaway is meant to be an escape from your daily routine, not a source of money worries. So to give you a bit more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.