Title: Windham Vacation Packages & Trips 2026 from CA $1,046 | Expedia.ca [Hotels in Windham](https://expedia.ca/Windham-Hotels.d10053.Travel-Guide-Hotels)[Vacation Rentals in Windham](https://expedia.ca/Windham-Vacation-Rentals.d10053.Travel-Guide-VacationRentals)[Flights to Windham](https://expedia.ca/Cheap-Flights-To-Windham.d10053.Travel-Guide-Flights)[Things to do in Windham](https://expedia.ca/Things-To-Do-In-Windham.d10053.Travel-Guide-Activities)[Windham Car Rentals](https://expedia.ca/Car-Rentals-In-Windham.d10053.Car-Rental-Guide) ![](https://images.trvl-media.com/place/10053/e35578b1-da57-445e-877f-214e815ca305.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windham 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 Windham Vacation With plenty of highlights as well as some hidden gems, this city is best experienced with a Windham vacation package. Book a hotel in Parkside, which is good for festivals, markets and walking. If your trip to Windham includes a little sightseeing, don't miss well-known attractions like [Maine Wildlife Park](https://www.expedia.ca/Maine-Wildlife-Park-Windham.d553248621532667988.Vacation-Attraction), [Riverside Municipal Golf Course](https://www.expedia.ca/Riverside-Municipal-Golf-Course-Portland.d6327744.Vacation-Attraction) and [MAGAN Trailhead](https://www.expedia.ca/MAGAN-Trailhead-Portland.d641530092651474944.Vacation-Attraction). Check out Expedia's wide range of travel options and begin planning your perfect vacation to Windham today. ## Top Windham Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Admiral Peary Inn](https://images.trvl-media.com/lodging/104000000/103130000/103126600/103126582/1bedf2ee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Admiral Peary Inn CA $1,046 per person Apr 3 - Apr 6 found 11 hours ago Roundtrip non-stop flight included Montreal (YUL) to Portland (PWM) 9.2/10 Wonderful! (44 reviews) Quaint bed-and-breakfast. Clean and comfortable. Would definitely stay again. Reviewed on Dec 8, 2025 ## Ready to book your vacation to Windham? Choose your dates ## Windham Hotel Deals ![Dormir](https://images.trvl-media.com/lodging/10000000/9320000/9312400/9312400/1c6ce74e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Dormir 965 Roosevelt Trail Windham ME Fully refundableReserve now, pay when you stay CA $150 CA $163 total Feb 9 - Feb 10 includes taxes & fees 8.8/10 Excellent! (999 reviews) clean room friendly staff Reviewed on Jan 25, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=9312400&PinnedHotelID=9312400&HadPinnedHotel=true®ionId=10053) ![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/b163ad24_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Clarion Hotel Portland Airport ME 1230 Congress St Portland ME Fully refundableReserve now, pay when you stay CA $105 CA $117 total Feb 16 - Feb 17 includes taxes & fees 8/10 Very Good! (1,343 reviews) Entire staff was top notch.Thanks to Drew mgr and Mathew.Recommend this place highly Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F02%2F2026&endDate=17%2F02%2F2026&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true®ionId=10053) ![Long Creek Hotel by IHG](https://images.trvl-media.com/lodging/1000000/30000/24300/24280/f3b41288_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Long Creek Hotel by IHG 171 Philbrook Ave South Portland ME Fully refundable CA $107 CA $116 total Feb 10 - Feb 11 includes taxes & fees 7.4/10 Good! (1,000 reviews) Room was clean, bed was large and comfortable, staff was friendly. Sadly however, The pool and hot tub were closed. Reviewed on Feb 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=10%2F02%2F2026&endDate=11%2F02%2F2026&selected=24280&PinnedHotelID=24280&HadPinnedHotel=true®ionId=10053) [See all 3,090 properties in Windham](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F02%2F2026&endDate=10%2F02%2F2026®ionId=10053) 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) ### What to do in Windham ![Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour](https://mediaim.expedia.com/localexpert/44927495/42f8f2e5-289d-480a-a822-cc8751cc6b66.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour CA $14 per traveller [](https://expedia.ca/things-to-do/downtown-portland-coastal-vibe-and-old-mansions-with-in-add-audio-tour.a44927495.activity-details) ![Portland Self-Guided Driving Audio Tour](https://mediaim.expedia.com/localexpert/45719150/c5757d24-772a-4314-9a5b-385c37350ecc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Portland Smartphone Audio Tour: Self-Guided Drive CA $23 per traveller [](https://expedia.ca/things-to-do/portland-smartphone-audio-tour-self-guided-drive.a45719150.activity-details) ![Ultimate Portland Self-Guided Driving GPS Audio Tour](https://mediaim.expedia.com/localexpert/44941422/00064774-1203-465f-8cee-e200125a2c6a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Ultimate Portland Self-Guided Driving GPS Audio Tour CA $23 per traveller **100%** of travellers recommend [](https://expedia.ca/things-to-do/ultimate-portland-self-guided-driving-gps-audio-tour.a44941422.activity-details) [See all activities in Windham](https://expedia.ca/things-to-do/search?rid=10053) ## Explore a world of travel with Expedia - 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