Title: Windham Vacation Packages & Trips 2026 from CA $1,284 | 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/1000000/900000/898700/898621/1a7f326f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Portland Harbor Hotel

Downtown Portland

CA $1,284

per person

May 25 - May 29

found 12 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Portland (PWM)

9.2/10 Wonderful! (1,776 reviews)

We could have moved right in and been happy for life. Flawless.

Reviewed on Mar 30, 2026

![Inn By The Sea](https://images.trvl-media.com/lodging/2000000/1550000/1542800/1542725/a8100548_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Inn By The Sea

CA $2,226

per person

May 25 - May 29

found 12 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Portland (PWM)

9.4/10 Exceptional! (304 reviews)

This was my first trip away since having kids 12 years ago. The staff was very friendly, helpful and attentive. The parking lot, lobby, halls and room were very clean. Our dinner and breakfast at the Inn were absolutely delicious. The ingredients were fresh and the flavors complimented each other well. It was difficult to make a choice on what to order. We didn't have a pet with us but did see several dogs during dining and were impressed with dog menu. I would highly recommend to anyone to stay at the Inn and if you are unable to at least have a meal in the restaurant. We are already planning a longer stay next time.

Reviewed on Mar 30, 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 15 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

![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 $1,791

per person

May 25 - May 29

found 12 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) 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

![The Docent's Collection at 121 Middle Street](https://images.trvl-media.com/lodging/39000000/38780000/38770100/38770068/148140d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Docent's Collection at 121 Middle Street

Downtown Portland

CA $2,918

per person

Jun 26 - Jun 28

found 15 hours ago

Roundtrip flight included

Presque Isle (PQI) to Portland (PWM)

9.6/10 Exceptional! (275 reviews)

Beautiful space, clean room, friendly and accommodating staff, excellent location

Reviewed on Apr 5, 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 $183

CA $200 total

Apr 20 - Apr 21

includes taxes & fees

8.8/10 Excellent! (999 reviews)

Enjoyed my stay. Very reliable.

Reviewed on Mar 20, 2026

[](https://expedia.ca/Hotel-Search?startDate=20%2F04%2F2026&endDate=21%2F04%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 $194

CA $214 total

Apr 22 - Apr 23

includes taxes & fees

[](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%2F04%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true&regionId=10053)

![Cambria Hotel Portland Downtown-Old Port](https://images.trvl-media.com/lodging/78000000/77990000/77981700/77981687/2540bb39_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET Portland ME

Fully refundable

CA $158

CA $212 total

Apr 9 - Apr 10

includes taxes & fees

9.4/10 Exceptional! (1,186 reviews)

Clean, quiet, good stay.

Reviewed on Apr 6, 2026

[](https://expedia.ca/Hotel-Search?startDate=09%2F04%2F2026&endDate=10%2F04%2F2026&selected=77981687&PinnedHotelID=77981687&HadPinnedHotel=true&regionId=10053)

[See all 3,181 properties in Windham](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=07%2F04%2F2026&endDate=08%2F04%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 $13

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 $21

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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