Windham Vacations

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Find the Best Windham Vacation Packages

Windham Hotel Deals

Dormir

Dormir

3 out of 5
965 Roosevelt Trail, Windham, ME
Fully refundableReserve now, pay when you stay
The price is ￥34,000 per night from Aug 13 to Aug 14
￥34,000
￥37,060 total
Aug 13 - Aug 14
includes taxes & fees
8.8/10 Excellent! (999 reviews)
"Bed a little lumpy. Otherwise perfect... great location!"

Reviewed on Jul 31, 2025

Dormir
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is ￥16,181 per night from Aug 24 to Aug 25
￥16,181
￥17,638 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,124 reviews)
"Good"

Reviewed on Aug 4, 2025

Days Inn by Wyndham Airport/Maine Mall
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is ￥15,767 per night from Aug 17 to Aug 18
￥15,767
￥17,186 total
Aug 17 - Aug 18
includes taxes & fees
7.4/10 Good! (123 reviews)
"We loved the indoor pool, the breakfast, and the mural in the room!"

Reviewed on Aug 6, 2025

Germaine Inn South Portland
See all 3,295 properties in Windham
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.

What to do in Windham

Port City Light Cruise

Port City Lights Cruise

￥5,760
per adult
100% of travellers recommend
Port City Lights Cruise
Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

￥10,191
per adult
Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks
Portland: Private Island Fort Tour

Portland: Private Island Fort Tour

￥20,381
per adult
Portland: Private Island Fort Tour
See all activities in Windham

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?

  1. Pick your dates: What you'd like to do in Windham and your favorite season can help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.