Windham Vacations from $488

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Your Windham Vacation

With plenty of highlights as well as some hidden gems, this city is best experienced with a Windham vacation package. Book a hotel in Parkside, which is good for festivals, markets and walking. If your trip to Windham includes a little sightseeing, don't miss well-known attractions like Maine Wildlife Park, Riverside Municipal Golf Course and MAGAN Trailhead. Check out Expedia's wide range of travel options and begin planning your perfect vacation to Windham today.

The Latest Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
8.8/10 Excellent! (793 reviews)
The staff were friendly and helpful. The Inn was clean and in a convenient location. Trolley pick up was right out front of the Inn to take us to the downtown area and beach. Enjoyed the pool. We did not take advantage of the river kayaking/paddle boarding. Next trip.

Reviewed on Jul 10, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (1,003 reviews)
Everything about this location is five stars

Reviewed on Jul 6, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (209 reviews)
We loved our stay at The Docent's Collection, would come here again.

Reviewed on Jul 8, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.2/10 Wonderful! (1,533 reviews)
The staff were super friendly and helpful. The room was beautiful and the garden atmosphere was fantastic. I would recommend this hotel.

Reviewed on Jul 10, 2025

Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
7.8/10 Good! (1,034 reviews)
Quick check in. The staff has been very helpful. I am on a motorcycle, it has been raining, they offered towels to dry the bike and found some towels i could take with me, as my seat is very soggy.

Reviewed on Jul 10, 2025

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Discover the most popular places to visit in Windham

Maine Wildlife Park

4.5/5(6 reviews)

Meet the animals who live at Maine Wildlife Park during your trip to Windham. While in this family-friendly area, you can savor the top-notch restaurants.

Maine Wildlife Park

Seacoast Adventure

5/5(4 reviews)

Bring the family to Seacoast Adventure and enjoy some excitement at this amusement park in Windham. Stroll along this family-friendly area's lakeside, or simply enjoy its restaurants.

Seacoast Adventure

What to do in Windham

Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

$9
per adult
Downtown Golden Adventure Quest Experience in Portland
Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

$67
per adult
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Sunset Lighthouse Cruise Tour from Casco Bay

Sunset Lighthouse Cruise Tour from Casco Bay

$56
per adult
90% of travellers recommend
Sunset Lighthouse Cruise Tour from Casco Bay
See all activities in Windham

Windham Hotel Deals

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
$129 nightly
The price is $141 total per night from Jul 13 to Jul 14
$141 total
Jul 13 - Jul 14
Total includes taxes and fees
7.8/10 Good! (1,011 reviews)
"Great for the price, clean rooms and good breakfast"

Reviewed on Jul 10, 2025

Days Inn by Wyndham Airport/Maine Mall
Clarion Hotel Portland
Clarion Hotel Portland
2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $168 total per night from Jul 14 to Jul 15
$168 total
Jul 14 - Jul 15
Total includes taxes and fees
7.8/10 Good! (1,010 reviews)
"Nice hotel close to the airport with shuttle service"

Reviewed on Jul 7, 2025

Clarion Hotel Portland
Ramada Plaza by Wyndham Portland
Ramada Plaza by Wyndham Portland
3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
$153 nightly
The price is $169 total per night from Jul 13 to Jul 14
$169 total
Jul 13 - Jul 14
Total includes taxes and fees
7.6/10 Good! (1,029 reviews)
"Quick check in. The staff has been very helpful. I am on a motorcycle, it has been raining, they offered towels to dry the bike and found some towels i could take with me, as my seat is very soggy."

Reviewed on Jul 10, 2025

Ramada Plaza by Wyndham Portland
See all 3,332 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.

Find the Best Windham Vacation Packages

Windham Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
State Theatre, East End Beach and Portland Museum of Art

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Frequently asked questions

How much does a Windham vacation package cost?
Offering great value package deals from $488 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?
June, July and October are the best times to search for cheap Windham vacation packages. Traveling in less busy periods means you can generally find reduced prices on flights and accommodations.
How many days is enough for Windham?
Usually, a handful of days is enough to tick off the major sights during your Windham vacation. But if you want to have more time to relax or go on day trips, think about extending your trip.
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 travel dates: What you want to do in Windham and your preferred season can help you decide when to get away.
  2. Plan your budget wisely: On top of the price of your stay, you should consider other expenses too. These include transportation, flights and food. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Windham.
  3. Organize your Windham escape with Expedia's trip planning tool: Search for and book stays and experiences all in one place. You can also collaborate with your group to plan an unforgettable trip to Windham together.
  4. Set the duration of your trip: Start by compiling a list of the attractions and activities you want to experience in Windham. Then, estimate how long you'll need at each, along with any travel time.
  5. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose a Windham vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Have a look at our travel guide to find some incredible things to do in Windham. Book tickets or make reservations in advance to save time and avoid the hassle of searching for activities once you arrive.

Does Expedia offer Book Now, Pay Later Windham vacation packages?
If you're anything like us, you love traveling but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Windham break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.