Windham Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 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
Find the Best Windham Vacation Packages
Windham Hotel Deals
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
￥17,100
￥18,639 total
Oct 19 - Oct 20
includes taxes & fees
8.4/10 Very Good! (3,003 reviews)
"The staff at the front desk checked us in and out efficiently but lacked the warmth and hospitality. The bathroom stall was also slippery. Almost fell. Need to put some kind of traction to prevent falls."
Reviewed on Sep 18, 2026
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
￥13,805
￥15,047 total
Oct 18 - Oct 19
includes taxes & fees
6.4/10 (1,133 reviews)
"It was barely acceptable. Tun looked dirty and the main door showed signs of damage. The door to connecting room could not be deadbolt locked. Two flimsy back up locks were able to be engaged."
Reviewed on Sep 18, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
￥16,788
￥18,574 total
Oct 19 - Oct 20
includes taxes & fees
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
Portland: Trolley City Tour with Portland Head Light Stop
￥9,765
per adult
100% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
￥9,336
per adult
Sunset Windjammer Cruise Along the Coast of Portland Maine
￥12,184
per adult
90% of travellers recommend
Frequently asked questions
How much does a Windham vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Windham costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Windham?
If you're looking to snag a cheap Windham vacation package, consider visiting in January, February and November. You'll generally find lower rates on hotels and airfares during these quieter months — perfect for a budget-friendly break.
How many days is enough for Windham?
With a well-organized travel plan, you can easily hit the most popular Windham attractions in a few days. But if you prefer to discover hidden spots or go on day trips, consider 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 preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Windham package deal right away, just play around with 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 underway.
Is it cheaper to book a Windham vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking hotels and flights individually. Better still, you can personalize your Windham getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Windham?
If you have your Windham travel dates finalized, book early to score some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Windham?
- Pick your dates: What you'd like to do in Windham and your favorite season can help you decide when to travel.
- Set your budget: Factor in expenses like food, flights and transportation when calculating how much to put aside for your trip to Windham. Then, pick a property that works with your budget, whether that's a low-cost option or a deluxe retreat.
- Decide how long to go away for: Now that you know more about Windham, you can work out the right length of your break. Create a draft itinerary and allocate enough time to get through everything on your must-do list.
- Bundle your accommodations and airfare: Once you've nailed down your travel dates and duration, lock in the perfect Windham vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
