Windham Holidays
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- Better togetherSave up to S$1,300 when you book a flight and hotel together*
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Top hotels in Windham
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
S$118
1 Nov - 2 Nov
includes taxes & fees
8.2/10 Very good! (1,771 reviews)
"Everything was good. We needed to be near the bus/train depot so this was perfect. Poo and hot tub a plus. Disappointed that you had to buy breakfast. Thought it came with the room."
Reviewed on 12 Oct, 2026
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
S$180
11 Nov - 12 Nov
includes taxes & fees
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
S$140
25 Oct - 26 Oct
includes taxes & fees
8.2/10 Very good! (1,011 reviews)
"This hotel is a modest place just outside of Portland. The price/ value is good. But it’s a bit dated. The fitness room has only a few pieces of equipment and for a hotel this big it needs more. The hot tub was lovely but very small. The indoor pool did not open until 9:00am which was unfortunate ..."
Reviewed on 12 Oct, 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
Portland: Casco Bay Morning Lighthouse Cruise
S$75
per adult
80% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
S$98
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.
