Title: Westport Vacation Packages & Trips 2026 from CA $943 | Expedia.ca [Hotels in Westport](https://expedia.ca/Westport-Hotels.d553248635975847929.Travel-Guide-Hotels)[Vacation Rentals in Westport](https://expedia.ca/Westport-Vacation-Rentals.d553248635975847929.Travel-Guide-VacationRentals)[Westport Car Rentals](https://expedia.ca/Car-Rentals-In-Westport.d553248635975847929.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248635975847929/b7aff5b2-5d85-4d12-bb1d-fcb92777bb9a.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Westport Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## 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 Westport Vacation With a vacation package to Westport, say goodbye to travel planning and hello to trouble-free adventure. Every detail of your getaway has been taken care of before you go, so you can get on with experiencing this exciting city. If your trip to Westport includes a little sightseeing, check out well-known attractions like [Brooks Point](https://www.expedia.ca/Brooks-Point-Maine.d553248635975748323.Vacation-Attraction), [Castle Tucker](https://www.expedia.ca/Castle-Tucker-Wiscasset.d6334533.Vacation-Attraction) and [Monkey C Monkey Do](https://www.expedia.ca/Monkey-C-Monkey-Do-Wiscasset.d553248621532668218.Vacation-Attraction). Browse Expedia's wide range of travel options and begin planning your ideal vacation to Westport today. ## Top Westport Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Newagen Seaside Inn](https://images.trvl-media.com/lodging/9000000/8090000/8082900/8082897/e842ee11_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Newagen Seaside Inn CA $943 per person Jul 1 - Jul 3 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to Portland (PWM) 9.4/10 Exceptional! (341 reviews) IT WAS CHARMING AND BEAUTIFUL. The restaurant was wonderful, all the staff was first class, would love to go back. Reviewed on Oct 14, 2025 ![Blind Tiger Portland - Danforth Street.](https://images.trvl-media.com/lodging/1000000/210000/200300/200246/7a3d1c09_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Blind Tiger Portland - Danforth Street. West End CA $1,904 per person Jul 1 - Jul 3 found 1 day ago Roundtrip flight included Winnipeg (YWG) to Portland (PWM) 9.6/10 Exceptional! (175 reviews) The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend! Reviewed on Mar 10, 2026 ![Ogunquit River Inn & Suites](https://images.trvl-media.com/lodging/2000000/1200000/1198100/1198069/6221f2a7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ogunquit River Inn & Suites CA $2,059 per person Jun 26 - Jun 28 found 6 hours ago Roundtrip flight included Presque Isle (PQI) to Portland (PWM) 9/10 Wonderful! (1,000 reviews) The room was very clean! Reviewed on Oct 31, 2025 ![Waldo Emerson Inn](https://images.trvl-media.com/lodging/2000000/1560000/1555300/1555270/8a901c9c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldo Emerson Inn CA $1,792 per person Jul 1 - Jul 3 found 1 day ago Roundtrip flight included Winnipeg (YWG) to Portland (PWM) 8.8/10 Excellent! (339 reviews) My husband and I (and our dog) had a lovely three night stay. The hosts Amelia and Ron were so welcoming, and made us delicious breakfasts. They filled us in on the history of the Inn and the neighboring area. Our room was comfortable and cozy, and we enjoyed the hot cocoa and soft drinks that were always available. Just the post-Christmas getaway we needed. Reviewed on Dec 29, 2025 ![Dormir](https://images.trvl-media.com/lodging/10000000/9320000/9312400/9312400/eaaa6212_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Dormir CA $1,328 per person Jul 1 - Jul 3 found 1 day ago Roundtrip flight included Winnipeg (YWG) to Portland (PWM) 8.8/10 Excellent! (999 reviews) Enjoyed my stay. Very reliable. Reviewed on Mar 20, 2026 ## Ready to book your vacation to Westport? Choose your dates ## Westport Hotel Deals ![Gorgeous Waterfront Home on Westport Island with 2 Sunrooms](https://images.trvl-media.com/lodging/73000000/72400000/72395900/72395846/w3904h2591x0y12-145a57c8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Gorgeous Waterfront Home on Westport Island with 2 Sunrooms Westport Island ME 9.4/10 Exceptional! (57 reviews) Beautiful home with plenty of amenities in a wonderful location. Reviewed on Dec 14, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=20%2F04%2F2026&endDate=21%2F04%2F2026&selected=72395846&PinnedHotelID=72395846&HadPinnedHotel=true®ionId=553248635975847929) [](https://expedia.ca/Hotel-Search?startDate=20%2F04%2F2026&endDate=21%2F04%2F2026&selected=72395846&PinnedHotelID=72395846&HadPinnedHotel=true®ionId=553248635975847929) ![Unique oceanfront home with a deck, tons of natural light, & amazing views](https://images.trvl-media.com/lodging/58000000/57220000/57216900/57216850/dc210a4f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Unique oceanfront home with a deck, tons of natural light, & amazing views Wiscasset 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 [Get rates](https://expedia.ca/Hotel-Search?startDate=20%2F04%2F2026&endDate=21%2F04%2F2026&selected=57216850&PinnedHotelID=57216850&HadPinnedHotel=true®ionId=553248635975847929) [](https://expedia.ca/Hotel-Search?startDate=20%2F04%2F2026&endDate=21%2F04%2F2026&selected=57216850&PinnedHotelID=57216850&HadPinnedHotel=true®ionId=553248635975847929) ![Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.](https://images.trvl-media.com/lodging/65000000/64610000/64605100/64605061/f82f403a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast. Westport ME 9.8/10 Exceptional! (100 reviews) We had a fantastic stay this January. The house was perfect with great heating gas fireplace, pellet stove and wood stove. Also a wonderful fire pit outside and a wonderful outside hot tub. We used everything and had exceptional weather as well. Highly recommend it. The host is very reachable and ... Reviewed on Jan 19, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=20%2F04%2F2026&endDate=21%2F04%2F2026&selected=64605061&PinnedHotelID=64605061&HadPinnedHotel=true®ionId=553248635975847929) [](https://expedia.ca/Hotel-Search?startDate=20%2F04%2F2026&endDate=21%2F04%2F2026&selected=64605061&PinnedHotelID=64605061&HadPinnedHotel=true®ionId=553248635975847929) [See all 1,634 properties in Westport](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=07%2F04%2F2026&endDate=08%2F04%2F2026®ionId=553248635975847929) 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 Westport #### 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) ## 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