Windham Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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, 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.
The Docent's Collection at 121 Middle Street
Downtown Portland
CA $965
per person
Dec 10 - Dec 13
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Portland (PWM)
9.6/10 Exceptional! (382 reviews)
Other than being a little hard to find, this spot was wonderful and so much nicer than a hotel room! Great location.
Reviewed on Sep 18, 2026
The Docent's Collection at 178 Middle Street
Downtown Portland
CA $1,032
per person
Dec 10 - Dec 13
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Portland (PWM)
9.6/10 Exceptional! (61 reviews)
Staff was very very good and super quick to respond.. I really liked the location for my visit bc everything was easily walkable. Room was comfortable but a little interesting walking all the way across for bathroom. A few small glitches with electrical probably just bc it’s done recently renovated.
Reviewed on Sep 18, 2026
The Francis
Parkside
CA $1,777
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (406 reviews)
The Francis is an "old bones" hotel that has been updated to a 21st-century experience.
The staff was attentive to our every need and up to date on the local area. The Hotel is just west of the Arts District and has many neighborhood restaurants within walking distance.
The room was clean and comfortable and had a small reading area. The bathroom was modern and clean. Breakfast was delivered to our room in the morning from a local bakery. The room had a "pour-over" coffee pot with instructions that made some great coffee and an electric kettle for my wife to enjoy hot tea at any time of the day.
Special shout-out to Devin at the front desk for his recommendations and assistance.
Reviewed on Sep 21, 2026
Ready to book your vacation to Windham?
Windham Hotel Deals
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
CA $123
CA $135 total
Oct 18 - Oct 19
includes taxes & fees
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
CA $154
CA $168 total
Oct 18 - Oct 19
includes taxes & fees
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
CA $151
CA $167 total
Oct 18 - Oct 19
includes taxes & fees
8.2/10 Very good! (1,716 reviews)
"No bar like shown in description"
Reviewed on Sep 22, 2026
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.
Stay near popular Windham attractions
beach near Boathouse Beach Lane
Why not spend a lazy afternoon at beach near Boathouse Beach Lane during your trip to Windham? Stroll along this family-friendly area's lakeside, or simply enjoy its restaurants.
What to do in Windham
Sunset Windjammer Cruise Along the Coast of Portland Maine
CA $107
per adult
90% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
CA $82
per adult
Frequently asked questions
How much does a Windham vacation package cost?
You'll find cheap prices from CA $965 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?
- Choose your dates: What you plan to do in Windham and your preferred season will help you decide when to go.
- 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.
- 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.
- 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
