Title: Wiscasset Vacation Packages & Trips 2025/2026 from CA $711 | Expedia.ca [Hotels in Wiscasset](https://expedia.ca/Wiscasset-Hotels.d183305.Travel-Guide-Hotels)[Vacation Rentals in Wiscasset](https://expedia.ca/Wiscasset-Vacation-Rentals.d183305.Travel-Guide-VacationRentals)[Things to do in Wiscasset](https://expedia.ca/Things-To-Do-In-Wiscasset.d183305.Travel-Guide-Activities)[Wiscasset Car Rentals](https://expedia.ca/Car-Rentals-In-Wiscasset.d183305.Car-Rental-Guide) ![](https://images.trvl-media.com/place/183305/b3e620e7-81ed-45ee-8985-a08e7980a57e.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Wiscasset Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Debbie Hall - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 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](https://www.expedia.ca/Lincoln-County-Jail-Museum-Wiscasset.d553248621533117438.Vacation-Attraction), [Wiscasset, Waterville and Farmington Railway Museum](https://www.expedia.ca/Wiscasset-Alna.d676705134567596032.Vacation-Attraction) and [Little Point](https://www.expedia.ca/Little-Point-Boothbay-Harbor.d553248635975748328.Vacation-Attraction). 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 Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/c8a0ec33_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Regency Hotel & Spa Downtown Portland CA $711 per person Oct 27 - Oct 30 found 1 day ago Roundtrip flight included Toronto (YYZ) to Portland (PWM) 9.4/10 Exceptional! (1,424 reviews) We were a 3-10 minute from almost everything. Reviewed on Sep 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-27/2025-10-30/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=920050&paandie=true&dealMarker=jRLnAqJiSJIRWGU50-AhCQG3cHc97I6v0SEm1qNKDEf6rmMX3ZfxxKvpm7eo_cbL) ![Cliff House Maine](https://images.trvl-media.com/lodging/4000000/3990000/3981200/3981160/eb122fc0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cliff House Maine CA $1,855 per person Oct 27 - Oct 30 found 1 day ago Roundtrip flight included Toronto (YYZ) to Portland (PWM) 9.4/10 Exceptional! (1,007 reviews) The property and staff were excellent. There was an issue with the restaurant Tiller as there was not enough staff to serve the guests. Reviewed on Sep 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-27/2025-10-30/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=3981160&paandie=true&dealMarker=jRLnAqJiSJIRWGU50-AhCQG3cHc97I6v0SEm1qNKDEcIyyw29lAoGuqr6PdXYhGH) ![The Weldon Hotel](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/38875013_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Weldon Hotel Downtown Portland CA $964 per person Oct 27 - Oct 30 found 1 day ago Roundtrip flight included Toronto (YYZ) to Portland (PWM) 9.8/10 Exceptional! (79 reviews) The property was extreme clean. Staff was extremely helpful and responded quickly to requests. Very safe location. Loved that there was a washer and dryer and also a small kitchen area in the property. Reviewed on Sep 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-27/2025-10-30/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=107321604&paandie=true&dealMarker=RNUtusT_53FWpfHsM_TBG5PvxSfvuZFi7A5Ao2Kv0MtZDX9rYfVG-QOQMiyNWsq8) ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Harbor Hotel Downtown Portland CA $726 per person Oct 27 - Oct 30 found 1 day ago Roundtrip flight included Toronto (YYZ) to Portland (PWM) 9.2/10 Wonderful! (1,581 reviews) The sitting area was beautiful. Lawn size games and fire pits in every area like a private camp fire. Reviewed on Sep 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-27/2025-10-30/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=898621&paandie=true&dealMarker=jRLnAqJiSJIRWGU50-AhCQG3cHc97I6v0SEm1qNKDEcOMXDytmc5QEA_rEenapvJ) ![Kennebunkport Captains Collection](https://images.trvl-media.com/lodging/14000000/13280000/13279300/13279259/285f2526_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kennebunkport Captains Collection CA $1,019 per person Oct 27 - Oct 30 found 1 day ago Roundtrip flight included Toronto (YYZ) to Portland (PWM) 9.4/10 Exceptional! (622 reviews) Very nice spot close to everything Reviewed on Sep 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-27/2025-10-30/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=13279259&paandie=true&dealMarker=jRLnAqJiSJIRWGU50-AhCQG3cHc97I6v0SEm1qNKDEdoloLVGEStIyAOJfTA6-v2) ## Ready to book your vacation to Wiscasset? Choose your dates ## Wiscasset Hotel Deals ![Make Shimmering River Retreat your Maine Coastal getaway!](https://images.trvl-media.com/lodging/68000000/67460000/67450900/67450866/95405adf_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Make Shimmering River Retreat your Maine Coastal getaway! Westport Island 9.6/10 Exceptional! (38 reviews) "Check in was easy. The kitchen was extremely well stocked down to a lobster pot to our delight.The setting is beautiful and we very much enjoyed the two level deck. There is a bit of a hike to get to the river. All and all a very peaceful relaxing location. We had 9 adults and 4 children and were ..." Reviewed on Aug 9, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=04%2F10%2F2025&endDate=05%2F10%2F2025&selected=67450866&PinnedHotelID=67450866&HadPinnedHotel=true®ionId=183305) [](https://expedia.ca/Hotel-Search?startDate=04%2F10%2F2025&endDate=05%2F10%2F2025&selected=67450866&PinnedHotelID=67450866&HadPinnedHotel=true®ionId=183305) ![Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.](https://images.trvl-media.com/lodging/65000000/64610000/64605100/64605061/5353cccc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast. Westport 9.8/10 Exceptional! (95 reviews) "A beautiful home in a beautiful place. Perfect for large families." Reviewed on Aug 17, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=04%2F10%2F2025&endDate=05%2F10%2F2025&selected=64605061&PinnedHotelID=64605061&HadPinnedHotel=true®ionId=183305) [](https://expedia.ca/Hotel-Search?startDate=04%2F10%2F2025&endDate=05%2F10%2F2025&selected=64605061&PinnedHotelID=64605061&HadPinnedHotel=true®ionId=183305) ![Unique oceanfront home with a deck, tons of natural light, & amazing views](https://images.trvl-media.com/lodging/58000000/57220000/57216900/57216850/32073ab6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Unique oceanfront home with a deck, tons of natural light, & amazing views Wiscasset 8.4/10 Very Good! (40 reviews) "The place is lovely and well situated. Some maintenance work needs to be done on the windows and doors. The management team was very responsive to my request for removal of garbage by former guests that had been placed outside the front door and not up in the dumpster! Would highly recommend this ..." Reviewed on Aug 18, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=04%2F10%2F2025&endDate=05%2F10%2F2025&selected=57216850&PinnedHotelID=57216850&HadPinnedHotel=true®ionId=183305) [](https://expedia.ca/Hotel-Search?startDate=04%2F10%2F2025&endDate=05%2F10%2F2025&selected=57216850&PinnedHotelID=57216850&HadPinnedHotel=true®ionId=183305) [See all 1,763 properties in Wiscasset](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=21%2F09%2F2025&endDate=22%2F09%2F2025®ionId=183305) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### 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. [](https://expedia.ca/Castle-Tucker-Wiscasset.d6334533.Vacation-Attraction) ### What to do in Wiscasset ![Boothbay Harbor Cruise: Lighthouses, Lobster Haul, and Seals](https://mediaim.expedia.com/localexpert/44641949/2afc8460-cb6e-455f-b9f3-bff7814551f0.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boothbay Harbor Cruise: Lighthouses, Lobster Haul, and Seals CA $56 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/boothbay-harbor-cruise-lighthouses.a44641949.activity-details) ![Schooner Applejack Sunset Sail Tour in Boothbay Harbor ](https://mediaim.expedia.com/localexpert/46153504/4a470dbb-9d7f-4c8e-8fac-5408ee7805f3.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Schooner Applejack Sunset Sail Tour in Boothbay Harbor CA $82 per adult [](https://expedia.ca/things-to-do/schooner-applejack-sunset-sail-tour-in-boothbay-harbor.a46153504.activity-details) ![Boothbay: Lighthouses & Islands Harbor Cruise](https://mediaim.expedia.com/localexpert/44646951/7fddcb25-9200-4a0b-b06e-618af7ddd873.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boothbay: Lighthouses & Islands Harbor Cruise CA $56 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/boothbay-lighthouses-islands-harbor-cruise.a44646951.activity-details) [See all activities in Wiscasset](https://expedia.ca/things-to-do/search?rid=183305) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)