Windham Vacations from $491

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $756, price is now $491 per person
$491
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Great location beautiful hotel

Reviewed on Jan 9, 2026

The McKernan Inn

The McKernan Inn

3 out of 5
Price was $793, price is now $543 per person
$543
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!

Reviewed on Dec 27, 2025

The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $861, price is now $635 per person
$635
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
This was a great stay! Had everything we wanted. Location was excellent.

Reviewed on Dec 24, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $1,458, price is now $1,082 per person
$1,082
per person
Apr 3 - Apr 6
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
The room along with the view was spectacular - Beautifully decorated - Clean - Crisp - The Staff - Beyond Helpful!! The location overlooking the Atlantic Ocean even this time of year with the sun and the ocean waves hitting the rocks was like out of a movie!! Their restaurants 5 star in my opinion!! Just the people they have working looking out for you and making sure you are having an experience of a lifetime!! Thank you again Cliff House - See you very soon!!!

Reviewed on Jan 6, 2026

River View Resort

River View Resort

2.5 out of 5
Price was $678, price is now $509 per person
$509
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
8.8/10 Excellent! (297 reviews)
A bit old but everything was clean, the kitchen was well stocked for the meals we made, the pool and sauna were nice to use on the day freezing rain kept us indoors. I also like that they had board/card games available for us to bring back to our room. The staff were helpful and friendly. All in all, we really enjoyed our stay here.

Reviewed on Jan 8, 2026

Don't see what you're looking for?
See all available trips from Columbus to Windham
View all trips

Discover the most popular places to visit in Windham

Seacoast Adventure

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 Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

$15
per traveler
Portland Smartphone Audio Tour: Self-Guided Drive
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

$10
per traveler
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

$17
per traveler
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
See all activities in Windham

Windham Hotel Deals

Dormir

Dormir

3 out of 5
965 Roosevelt Trail Windham ME
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $119 total per night from Jan 11 to Jan 12
$119 total
Jan 11 - Jan 12
Total with taxes and fees
8.8/10 Excellent! (1,007 reviews)
Staff were great. Rooms clean and good breakfast.

Reviewed on Dec 29, 2025

Dormir
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $87 total per night from Jan 12 to Jan 13
$87 total
Jan 12 - Jan 13
Total with taxes and fees
7.8/10 Good! (1,319 reviews)
Front desk attendant was very pleasant and helpful. Room was clean and well stocked with towels and toiletries.

Reviewed on Jan 5, 2026

Clarion Hotel Portland Airport ME
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $108 total per night from Jan 26 to Jan 27
$108 total
Jan 26 - Jan 27
Total with taxes and fees
8.8/10 Excellent! (1,008 reviews)
Room was clean and had all amenities.

Reviewed on Jan 6, 2026

The Westin Portland Harborview
See all 3,076 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Windham vacation package cost?
Offering great value package deals from $491 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.