Title: Windham Vacation Packages & Trips 2026 from CA $1,065 | 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.

![84 Main ](https://images.trvl-media.com/lodging/8000000/7810000/7805200/7805164/f78a93a3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 84 Main 

CA $1,065

per person

Apr 11 - Apr 16

found 22 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

10/10 Exceptional! (52 reviews)

Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.

Reviewed on Dec 29, 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 $2,139

per person

May 7 - May 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9.4/10 Exceptional! (1,001 reviews)

Excellent stay! One of the best in New England!

Reviewed on Feb 22, 2026

![Ogunquit River Inn & Suites](https://images.trvl-media.com/lodging/2000000/1200000/1198100/1198069/c97d3fbb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Ogunquit River Inn & Suites

CA $1,080

per person

May 7 - May 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9/10 Wonderful! (1,001 reviews)

The room was very clean!

Reviewed on Oct 31, 2025

![The Weldon Hotel](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/38875013_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Weldon Hotel

Downtown Portland

CA $1,428

per person

May 7 - May 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9.8/10 Exceptional! (86 reviews)

Location is excellent. Short walking distance to every good restaurant and shop. The property was very nice and clean. The kitchen is very well equipped. The gym is very good sized for the size of the apartment building with 13 units in it. The management’s communication was prompt and friendly and responded to all of our wishes. However, the place is advertised as a hotel, but don’t expect services as in a hotel. It resembles more a short term rental home - no cleaning service and no lobby. Otherwise everything was very nice in the apartment and we had a great time.

Reviewed on Jan 3, 2026

![The McKernan Inn](https://images.trvl-media.com/lodging/106000000/105380000/105370700/105370688/f7ebd781_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The McKernan Inn

CA $1,081

per person

Apr 2 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9/10 Wonderful! (83 reviews)

We had a wonderful stay, breakfast was great

Reviewed on Feb 18, 2026

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_10053)

## 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 $180

CA $196 total

Feb 26 - Feb 27

includes taxes & fees

8.8/10 Excellent! (1,003 reviews)

Staff was friendly. Room and bathroom were very clean. Great location for Sebago Lake area

Reviewed on Feb 16, 2026

[](https://expedia.ca/Hotel-Search?startDate=26%2F02%2F2026&endDate=27%2F02%2F2026&selected=9312400&PinnedHotelID=9312400&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 $122

CA $135 total

Mar 15 - Mar 16

includes taxes & fees

8.8/10 Excellent! (1,007 reviews)

Location, clean rooms, pleasant staff

Reviewed on Feb 23, 2026

[](https://expedia.ca/Hotel-Search?startDate=15%2F03%2F2026&endDate=16%2F03%2F2026&selected=6273&PinnedHotelID=6273&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 $105

CA $117 total

Mar 24 - Mar 25

includes taxes & fees

8/10 Very Good! (1,379 reviews)

great location, no frills, clean and kind staff

Reviewed on Feb 23, 2026

[](https://expedia.ca/Hotel-Search?startDate=24%2F03%2F2026&endDate=25%2F03%2F2026&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true&regionId=10053)

[See all 3,095 properties in Windham](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F02%2F2026&endDate=26%2F02%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 $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)

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- [Scarborough Beach State Park ](https://www.expedia.ca/Scarborough-Beach-State-Park-Scarborough.d6327764.Vacation-Attraction)
- [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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