Title: Windham Vacation Packages & Trips 2026 from CA $1,154 | 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.

![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 $1,154

per person

Jun 3 - Jun 8

found 4 hours ago

Roundtrip flight included

Calgary (YYC) to Portland (PWM)

9/10 Wonderful! (1,000 reviews)

The room was very clean!

Reviewed on Oct 31, 2025

![Cliff House Maine](https://images.trvl-media.com/lodging/4000000/3990000/3981200/3981160/fe5a854b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cliff House Maine

Bald Head

CA $2,919

per person

Jun 3 - Jun 8

found 4 hours ago

Roundtrip flight included

Calgary (YYC) to Portland (PWM)

9.4/10 Exceptional! (1,007 reviews)

Check in was smooth and set the tone for a relaxed upscale experience. Valet available and doorman took our bags to the room. Room was great, beautiful ocean view, soft and silky sheets/down bedding. Pool and hot tub were amazing. Was so beautiful and peaceful hearing the waves crash against the rocks. Well worth it!

Reviewed on Mar 24, 2026

![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/1a7f326f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Portland Harbor Hotel

Downtown Portland

CA $1,369

per person

May 16 - May 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

9.2/10 Wonderful! (1,776 reviews)

Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great.

Reviewed on Mar 24, 2026

![USA Inn](https://images.trvl-media.com/lodging/13000000/12540000/12535100/12535042/e9711923_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### USA Inn

CA $2,179

per person

Jun 3 - Jun 8

found 4 hours ago

Roundtrip flight included

Calgary (YYC) to Portland (PWM)

8/10 Very Good! (767 reviews)

Parking was convenient. Staff was goo

Reviewed on Nov 1, 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 $1,782

per person

May 16 - May 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) 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

## Ready to book your vacation to Windham?

Choose your dates

## Windham Hotel Deals

![Dormir](https://images.trvl-media.com/lodging/10000000/9320000/9312400/9312400/eaaa6212_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Dormir

965 Roosevelt Trail Windham ME

Fully refundableReserve now, pay when you stay

CA $135

CA $148 total

Mar 30 - Mar 31

includes taxes & fees

8.8/10 Excellent! (1,000 reviews)

Enjoyed my stay. Very reliable.

Reviewed on Mar 20, 2026

[](https://expedia.ca/Hotel-Search?startDate=30%2F03%2F2026&endDate=31%2F03%2F2026&selected=9312400&PinnedHotelID=9312400&HadPinnedHotel=true&regionId=10053)

![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/c479d2b6_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 $164

CA $181 total

Apr 12 - Apr 13

includes taxes & fees

8.8/10 Excellent! (1,003 reviews)

The staff was very helpful. Breakfast was included. Full service, not continental. Really good food. Parking was validated. No surprises on put bill. Definitely recommended.

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true&regionId=10053)

![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/c90266f6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Fully refundable

CA $108

CA $119 total

Apr 8 - Apr 9

includes taxes & fees

8/10 Very Good! (1,404 reviews)

Clean room , nice pool area and quiet ,will say that the beds are kinda uncomfortable but if you’re there for a night it’s not too bad ! I’d come back again.

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F04%2F2026&endDate=09%2F04%2F2026&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true&regionId=10053)

[See all 3,151 properties in Windham](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F03%2F2026&endDate=27%2F03%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)

![Ultimate Portland Self-Guided Driving GPS Audio Tour](https://mediaim.expedia.com/localexpert/44941422/8edf0b39-e377-40e8-9427-6d82cf3b7f7d.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)

![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)

[See all activities in Windham](https://expedia.ca/things-to-do/search?rid=10053)

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- [Scarborough Vacations ](https://www.expedia.ca/Scarborough.d6809.Destination-Travel-Guides)
- [Sebago Lake State Park ](https://www.expedia.ca/Sebago-Lake-State-Park-Maine.d6174213.Vacation-Attraction)
- [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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