Windham Vacations from ₩503,648
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 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
The Latest Windham Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Ogunquit Tides Resort
₩665,307
per person
Sep 18 - Sep 21
found 20 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
8.8/10 Excellent! (1,009 reviews)
Room for 5 was perfect for one night. Clean rooms & property. Convenient location. Pool is not heated but it’s big!
Reviewed on Aug 17, 2026
Anchor Inn and Cottages Wells-Ogunquit
₩605,736
per person
Sep 18 - Sep 21
found 20 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
8.6/10 Excellent! (1,009 reviews)
Staff was friendly and room was clean, but was older and needed some updating. Door to bedroom would not close, and the bathroom sink was very small.
Reviewed on Aug 17, 2026
USA Inn
₩556,084
per person
Sep 17 - Sep 20
found 20 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
8/10 Very Good! (830 reviews)
Rapport qualité / prix décevant.
Personnel courtois.
Propreté des lieux communs 2/5- chambre 3,5/5.
Bien situé - possibilité de marcher vers la plage, permet d’éviter les frais de stationnement.
Aucune vue, aucune piscine.
Reviewed on Aug 16, 2026
Find the Best Windham Vacation Packages
Windham Hotel Deals
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
₩131,163
₩142,967 total
Sep 15 - Sep 16
includes taxes & fees
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
₩185,313
₩205,030 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very Good! (1,623 reviews)
"John at front desk went above and beyond for us. The free shuttle is a major plus. I wish the restaurant had been open but it was closed the days we were there"
Reviewed on Aug 17, 2026
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
₩132,904
₩144,865 total
Sep 7 - Sep 8
includes taxes & fees
6.4/10 (1,058 reviews)
"The room was clean and the air conditioner was quiet. The bathroom was spacious and clean. The breakfast was very good and the staff was very friendly and helpful. Parking was plentiful."
Reviewed on Aug 16, 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.
Frequently asked questions
How much does a Windham vacation package cost?
Offering great value package deals from ₩503,648 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.
