Title: Windham Vacation Packages & Trips 2026 from CA $700 | 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.

![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 $700

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

9.2/10 Wonderful! (1,668 reviews)

Room was very small and the view was of a building rooftop and brick wall. Pillows were cheap and not good, filled with foam pieces. Bed was hard. Oh, and the room next to us had at least 2 small dogs that barked at noises. Not a 4 star hotel or worth the price by any means. Good location. Will not be staying there again. We go to Portland often and this is the first hotel I've ever revised.

Reviewed on Dec 21, 2025

![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

Bald Head

CA $1,178

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

9.4/10 Exceptional! (1,001 reviews)

My husband and I had a wonderful time. Breakfast, lunch, and dinner was delicious, drinks were crafted just right. We absolutely loved the outdoor hot tub. Our stay was everything we expected. Thank you.

Reviewed on Dec 8, 2025

![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 $826

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

9.4/10 Exceptional! (1,512 reviews)

Very clean hotel, friendly staff, good food in the pub.

Reviewed on Dec 24, 2025

![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 $949

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

9.4/10 Exceptional! (649 reviews)

Amazing place. My favourite place to visit over the Christmas period. Will be back next year.

Reviewed on Dec 17, 2025

![Inn By The Sea](https://images.trvl-media.com/lodging/2000000/1550000/1542800/1542725/d0fca35d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Inn By The Sea

CA $947

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

9.4/10 Exceptional! (288 reviews)

Room was ready early friendly staff and room is better than expected

Reviewed on Nov 16, 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 $127

CA $139 total

Dec 29 - Dec 30

includes taxes & fees

8.8/10 Excellent! (999 reviews)

Awesome and cozy place.

Reviewed on Dec 11, 2025

[](https://expedia.ca/Hotel-Search?startDate=29%2F12%2F2025&endDate=30%2F12%2F2025&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 $115

CA $127 total

Dec 27 - Dec 28

includes taxes & fees

7.8/10 Good! (1,295 reviews)

Very happy with everything except there wasn’t free breakfast or coffee.

Reviewed on Dec 23, 2025

[](https://expedia.ca/Hotel-Search?startDate=27%2F12%2F2025&endDate=28%2F12%2F2025&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 $134

CA $148 total

Jan 11 - Jan 12, 2026

includes taxes & fees

8.8/10 Excellent! (1,002 reviews)

Helpful staff

Reviewed on Dec 17, 2025

[](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true&regionId=10053)

[See all 3,093 properties in Windham](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F12%2F2025&endDate=26%2F12%2F2025&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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