Windham Vacation Packages

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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, Riverside Municipal Golf Course and MAGAN Trailhead. 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.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
7.8/10 Good! (1,032 reviews)
Great option to explore Portland.

Reviewed on Aug. 3, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,523 reviews)
Moderate luxury in the heart of everything Portland. Lots of shopping and dining in a short walk. The amenities fee is unusual.

Reviewed on Aug. 2, 2025

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (114 reviews)
The Blind Tiger was a gem. It was convenient and private enough to enjoy with staff available 24/7 with and questions. The room, lobby and all areas were immaculate and brilliantly arranged. I would definitely go again!

Reviewed on Jul. 23, 2025

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,004 reviews)
New Hotel Great Location

Reviewed on Jul. 31, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (218 reviews)
Fantastic place to stay when visiting Portland. The location can't be beat -- within a couple of blocks to the ferry terminal and Old Town shops and restaurants. The building is next to a police station and my family and I felt very safe. The unit was immaculate, modern, and fully equipped. Onsite parking was a huge bonus, as was the friendly and helpful staff. I would, without hesitation, stay at The Docent's Collection again.

Reviewed on Jul. 31, 2025

Ready to book your vacation to Windham?

 

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Windham Hotel Deals

Dormir

Dormir

3 out of 5
965 Roosevelt Trail, Windham, ME
Fully refundableReserve now, pay when you stay
The price is CA $318 per night from Aug 4 to Aug 5
CA $318
CA $347 total
Aug 4 - Aug 5
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Bed a little lumpy. Otherwise perfect... great location!"

Reviewed on Jul. 31, 2025

Dormir
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Aug 11 to Aug 12
CA $210
CA $232 total
Aug 11 - Aug 12
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"Breakfast food served out of a closet was a little odd, but it did taste good."

Reviewed on Aug. 1, 2025

Clarion Hotel Portland
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Aug 24 to Aug 25
CA $151
CA $165 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,101 reviews)
"Outside wasn't well kept up. The room was average, clean."

Reviewed on Jul. 31, 2025

Days Inn by Wyndham Airport/Maine Mall
See all 3,324 properties in Windham
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.
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What to do in Windham

Port City Light Cruise

Port City Lights Cruise

CA $53
per adult
100% of travellers recommend
Port City Lights Cruise
Portland: Maine Lighthouses Sightseeing Cruise with Drinks

Portland: Maine Lighthouses Sightseeing Cruise with Drinks

CA $95
per adult
Portland: Maine Lighthouses Sightseeing Cruise with Drinks
Portland: Sightseeing Cruise to Portland Head Light

Portland: Sightseeing Cruise to Portland Head Light

CA $49
per adult
98% of travellers recommend
Portland: Sightseeing Cruise to Portland Head Light
See all activities in Windham

Frequently asked questions

How much does a Windham vacation package cost?
You'll find cheap prices from CA $1,097 on Expedia for your Windham getaway. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Windham costs.
What are the cheapest months to go to Windham?
You can generally find lower prices and greater availability in January, February and November. Take a look at our cheap Windham vacation packages and you could score some excellent off-season deals.
How many days is enough for Windham?
With a well-planned schedule, you can easily hit the main Windham sights in a few days. But if you prefer to venture off the beaten track or go on day trips, think about booking your Windham vacation for longer.
How to find the best Windham package deals?
Start your search for a Windham package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Windham package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Windham adventure off to a flying start.
Is it cheaper to book a Windham vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Windham vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Windham?
If you have your Windham vacation dates locked in, book as early as you can to bag some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Windham?

  1. Choose your dates: What you plan to do in Windham and your preferred season will help you decide when to go.
  2. Work out your budget: Ensure you have enough money to cover everything from dining out and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to Windham.
  3. Decide how long to go for: Now that you know more about Windham, you can work out the ideal length of your vacation. Create a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Windham vacation package that brings all your bookings together.

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