Windham Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Top hotels in Windham
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
S$154
7 Sept - 8 Sept
includes taxes & fees
8.2/10 Very good! (1,632 reviews)
"It's a decent hotel in the process of doing some renovations. The restaurant does not appear to be open at the moment which was not a hardship for us. The cleaning staff was friendly and helpful. The front desk folks were great during the day. At night, while trying to call for the shuttle one night ..."
Reviewed on 28 Aug, 2026
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
S$94
27 Sept - 28 Sept
includes taxes & fees
7.2/10 Good! (738 reviews)
"Vacances"
Reviewed on 28 Aug, 2026
Waves Oceanfront Resort
87 W Grand Ave Old Orchard Beach ME
S$222
13 Sept - 14 Sept
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
Sunset Windjammer Cruise Along the Coast of Portland Maine
S$99
per adult
90% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
S$22
per traveller
100% of travellers recommend
Frequently asked questions
How much does a Windham holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday to Windham costs! Expedia's packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Windham?
If you're looking to snag a cheap Windham holiday 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-organised 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 holiday 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 holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking hotels and flights individually. Better still, you can personalise 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 holiday 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 favourite 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 accommodation and airfare: Once you've nailed down your travel dates and duration, lock in the perfect Windham holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
