Title: Windham Vacation Packages & Trips 2026 from CA $714 | 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.

![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/67608060_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Westin Portland Harborview

Downtown Portland

CA $714

per person

Apr 3 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Portland (PWM)

8.8/10 Excellent! (1,001 reviews)

Room was clean and had all amenities.

Reviewed on Jan 6, 2026

![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 $728

per person

Apr 3 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Portland (PWM)

9.2/10 Wonderful! (1,668 reviews)

Room was perfect! Super clean. Comfortable. Great location. Front desk employees were informative and so friendly at check in. Restaurant was delicious. Only downside was an extremely rude server (possibly manager, as he was not wearing a uniform) that waited on us during dinner.

Reviewed on Jan 8, 2026

![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 $759

per person

Apr 3 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Portland (PWM)

9.4/10 Exceptional! (1,512 reviews)

The room was great!! The amenities were great! The dining was great also!! It has been a wonderful experience!

Reviewed on Jan 7, 2026

![The Docent’s Collection – Thompson Block](https://images.trvl-media.com/lodging/39000000/38780000/38770100/38770068/e5025392_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Docent’s Collection – Thompson Block

Downtown Portland

CA $1,051

per person

Apr 3 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Portland (PWM)

9.6/10 Exceptional! (249 reviews)

This was a great stay! Had everything we wanted. Location was excellent.

Reviewed on Dec 24, 2025

![Cambria Hotel Portland Downtown-Old Port](https://images.trvl-media.com/lodging/78000000/77990000/77981700/77981687/50b0940a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cambria Hotel Portland Downtown-Old Port

East Bayside

CA $779

per person

Apr 3 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Portland (PWM)

9.4/10 Exceptional! (1,118 reviews)

Very nice hotel. Great location.

Reviewed on Jan 7, 2026

## 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 $152

CA $165 total

Jan 11 - Jan 12

includes taxes & fees

8.8/10 Excellent! (1,008 reviews)

Staff were great. Rooms clean and good breakfast.

Reviewed on Dec 29, 2025

[](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=9312400&PinnedHotelID=9312400&HadPinnedHotel=true&regionId=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 $108

CA $120 total

Jan 11 - Jan 12

includes taxes & fees

7.8/10 Good! (1,316 reviews)

The staff were great. Friendly and helpful! Loved the use of the shuttle into town

Reviewed on Jan 2, 2026

[](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true&regionId=10053)

![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/67608060_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Westin Portland Harborview

157 High St Portland ME

Fully refundableReserve now, pay when you stay

CA $136

CA $150 total

Jan 25 - Jan 26

includes taxes & fees

8.8/10 Excellent! (1,008 reviews)

Room was clean and had all amenities.

Reviewed on Jan 6, 2026

[](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true&regionId=10053)

[See all 3,086 properties in Windham](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=10%2F01%2F2026&endDate=11%2F01%2F2026&regionId=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 $21

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)

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- [Shaw Park ](https://www.expedia.ca/Shaw-Park-Gorham.d553248633861906803.Vacation-Attraction)
- [South Coast Vacations ](https://www.expedia.ca/South-Coast.d6057321.Destination-Travel-Guides)
- [South Portland Vacations ](https://www.expedia.ca/South-Portland.d6769.Destination-Travel-Guides)
- [State Theatre ](https://www.expedia.ca/State-Theatre-Downtown-Portland.d553248621532668181.Vacation-Attraction)
- [Westbrook Vacations ](https://www.expedia.ca/Westbrook.d56049.Destination-Travel-Guides)
- [Visit Westbrook ](https://www.expedia.ca/Westbrook.dx56049)

- [Car rentals in Avis Doubletree Hotel - 5780 Major Blvd ](https://www.expedia.ca/Avis-at-Doubletree-Hotel-5780-Major-Blvd-Orlando-Florida-USA.v56049.Car-Rental-Guide-Location)

- [Things to do in Standish ](https://www.expedia.ca/Things-To-Do-In-Standish.d3000440322.Travel-Guide-Activities)
- [Things to do in Westbrook ](https://www.expedia.ca/Things-To-Do-In-Westbrook.d56049.Travel-Guide-Activities)

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

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