Windham Vacations from $367

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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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $564, price is now $367 per person
$367
per person
Feb 15 - Feb 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
We were only here 1 night, but our room was clean and cozy. We walked right down the street for dinner at $3 Deweys and had a great time! We used our destination fee credit to have breakfast delivered and were thourouly dissapointed. I took one bite and knew something was not right, the potatoes were fried in rancid grease and inedibile. My husband had an omlet that was at least edibile but nothing special.

Reviewed on Nov 24, 2025

The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $713, price is now $396 per person
$396
per person
Feb 15 - Feb 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
This is in a great location and room was very spacious. Blind in bedroom was broken in down position so it was always dark in there. You are supposed to download an app that requires “always on” connection to Bluetooth to get in, but someone was available to give us card keys instead.

Reviewed on Nov 16, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $896, price is now $538 per person
$538
per person
Feb 15 - Feb 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
The property is beautiful, the staff is kind, and the rooms are spacious and clean. It was great to have a safe place to park the car while having so many things to do within walking distance. Being able to grab a quick breakfast before heading out was great too! We loved our stay here!

Reviewed on Nov 23, 2025

The Docent's Collection - Boyd Block

The Docent's Collection - Boyd Block

2 out of 5
Downtown Portland
Save 100% on your flight
Price was $889, price is now $559 per person
$559
per person
Feb 15 - Feb 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
10/10 Exceptional! (2 reviews)
Really nice and clean new hotel!

Reviewed on Oct 27, 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $839, price is now $529 per person
$529
per person
Feb 15 - Feb 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.8/10 Exceptional! (86 reviews)
Clean space, all the amenities needed for travel and an enjoyable stay. Location was perfect for walking to do many great local shops and restaurants. Staff was easy to contact and quick to respond

Reviewed on Nov 28, 2025

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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

$17
per traveler
Portland Smartphone Audio Tour: Self-Guided Drive
Tour of Palace & Monument of Marrakech

Tour of Palace & Monument of Marrakech

$39
per adult
Tour of Palace & Monument of Marrakech
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
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
$93 nightly
The price is $101 total per night from Nov 30 to Dec 1
$101 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
Room was clean ,staff was great. Thank you

Reviewed on Nov 23, 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
$84 nightly
The price is $93 total per night from Dec 1 to Dec 2
$93 total
Dec 1 - Dec 2
Total with taxes and fees
7.8/10 Good! (1,263 reviews)
clean, convenient. perfect place and close to portland.

Reviewed on Nov 26, 2025

Clarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $154 total per night from Nov 30 to Dec 1
$154 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (1,698 reviews)
Lovely old hotel in the heart of Portland. Loved the pantry, the staff were friendly and our room was quiet and comfortable. We got a great price from Hotels.com. We would love to stay here again but the normal rate is too steep for us.

Reviewed on Nov 26, 2025

Portland Harbor Hotel
See all 3,090 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 $367 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.

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