Windham Vacations from $415

Book a Hotel + Flight or Car together to unlock savings

Looking for sports, concerts, or music festivals? Opens in a new windowSearch event tickets

Your Windham Vacation

When a break in the city is calling, answer it with a vacation package to Windham. The neighborhood of Parkside, which is good for festivals, markets and walking, makes a great base for your adventures. Fill up your itinerary with tours of Maine Wildlife Park, Riverside Municipal Golf Course and MAGAN Trailhead, some of the things you just have to see during a trip to Windham. That dream Windham vacation is just a few clicks away. Browse flights, hotels and more on Expedia for a getaway that's tailored just for you.

The Latest Windham Vacation Packages

Price found within the past 48 hours. Click for updated prices.
River View Resort

River View Resort

2.5 out of 5
per person
Jul 19 - Jul 21
Roundtrip flight included
Cleveland (CLE) to Portland (PWM)
8.8/10 Excellent! (256 reviews)
This property was very clean with modern updates. The staff was kind and helpful, pool and hot tub were amazing. Highly recommend River View.

Reviewed on Mar 11, 2024

And. N B&B

And. N B&B

2 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
9.8/10 Exceptional! (28 reviews)
This is an elegant old house from the 1920s which the owners have renovated into a B&B. Andy, the owner/proprietor, is a friendly and interesting fellow who cooked a delicious breakfast for us and shared the history of this old mansion and its previous long time owner. If you are looking for a reasonably priced B&B near Portland this would be a good option.

Reviewed on Oct 4, 2023

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 5 - Aug 10
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
9/10 Wonderful! (1,191 reviews)
Great place to stay and see the waterfront area of Portland

Reviewed on May 15, 2024

Waldo Emerson Inn

Waldo Emerson Inn

3 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 25
Roundtrip flight included
New York (NYC) to Portland (PWM)
8.6/10 Excellent! (313 reviews)
Great place to relax and wind down. The innkeepers where excellent.

Reviewed on Oct 28, 2023

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
9.4/10 Exceptional! (900 reviews)
I asked the housekeeper to come back in an hour. She didnt . That is but when wr went out for dinner I asked the front desk to have a room refresh. They did the refresh but keft dirty mug, glasses and paper coffee cups on the bureau and did not pride fresh glasses/ mugs. Disappointing .

Reviewed on Feb 18, 2024

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

Windham Hotel Deals

Microtel Inn & Suites By Wyndham Windham
Microtel Inn & Suites By Wyndham Windham
3 out of 5
965 Roosevelt Trail, Windham, ME
Fully refundable
The price is $143 per night from May 19 to May 20
$143
$156 total
includes taxes & fees
May 19 - May 20
8.8/10 Excellent! (999 reviews)
"Property was very clean. Beds are extremely comfortable. The pool area was nice and clean. Their breakfast in the morning is pretty good as well."

Reviewed on May 10, 2024

Microtel Inn & Suites By Wyndham Windham
The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is $166 per night from Jun 2 to Jun 3
$166
$189 total
includes taxes & fees
Jun 2 - Jun 3
8.4/10 Very Good! (1,054 reviews)
"Always great! Sad about her lavender roll on missing this stay. Love that. Barbara was great at check in!!"

Reviewed on May 16, 2024

The Westin Portland Harborview
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is $224 per night from May 20 to May 21
$224
$248 total
includes taxes & fees
May 20 - May 21
9/10 Wonderful! (1,188 reviews)
A wonderful stay in Portland, ME
"I / we have stayed at the Portland Harbor Hotel at least 40 times over the years. I'm in the music business and one of the most talented "mastering" engineers on the planet (for LPs), Bob Ludwig, had his business here in Portland for decades. My assistant of also 40 + years lives near Portland and ..."

Reviewed on May 16, 2024

Portland Harbor Hotel
See all 2,866 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.

Explore other types of vacation packages

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?
From just $415. Yes, you read that right. Our Windham vacation packages are an easy way to stretch your budget. Combine your favorite hotels, flights and rental car and get to know this wonderful destination.
How do I get a cheap travel package to Windham?
Browse and lock in everything in one place with our Windham vacation packages. You’ll discover deals on hotels, flights, tours and more that’ll keep your wallet happy and your adventurous spirit full. And, with more than 550 airlines and 1,000,000 hotels all over the world to select from, you’ll have the flexibility to mix and match as you like.
Where should I stay in Windham?
With so much to do in Windham, it’s a good idea to lock in a hotel close to its attractions. Seacoast Adventure, Maine Wildlife Park and Mercy Primary Care are some fascinating ones to put on your to-do list.
What are the top hotels in Windham?
Get your vacation off to a good start by staying at Classic Maine Waterfront Cottage On Pristine Highland Lake Windham. It’s one of most popular properties in Windham. Another leading option is Highland Lakefront Cabin.
How far in advance should I book my Windham vacation?
While not all air carriers release tickets early, you can normally start comparing international airfares on Expedia up to a year in advance. This is the time when you can nab some fantastic deals. If you’re booking at the last minute, there’s a chance you could get lucky. Discounted prices occasionally appear only weeks before departure.
What does an Expedia Windham travel package include?
Car rentals, flights and hotels — we connect you to the best deals. All you have to do is decide on your preferred combination. After you’ve made your booking, you can add on the exciting stuff like tours and experiences. Our travel packages make it simple to create an unforgettable Windham trip.
What should I know before booking a Windham travel package?
A travel package can be customized for your circumstances and is a great way to stretch your hard-earned dollars. How much you include is totally up to you. Hotels, rental cars and flights — decide on a combination that works with your plans.
Can I choose my airline with a Windham Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you definitely can. Simply select the airline you want and craft your ideal Windham getaway.
If I'm not able to travel, can I cancel my Windham vacation package?
It’s difficult to predict what the future holds, so it’s good to know that you can change or cancel your Windham vacation package. If you booked in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal to find out more.

Discover the most popular places to visit in Windham

Image for Maine Wildlife Park

Maine Wildlife Park

4.5/5(6 reviews)

Take the family on an outing to Maine Wildlife Park during your trip to Windham. While you're here, you can savor the top-notch restaurants.

Maine Wildlife Park
Image for Seacoast Adventure

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
Image for Mercy Primary Care

Mercy Primary Care

Though Mercy Primary Care might be what brings you to town, perhaps you'll have a chance to explore more of Windham while you are here.

Mercy Primary Care

What to do in Windham

Image for Portland: Old Port Seafood Lovers Tour

Portland: Old Port Seafood Lovers Tour

$146
Per adult
Portland: Old Port Seafood Lovers Tour
Image for Sunset Lighthouse Harbor Cruise from Portland's Old Port

Sunset Lighthouse Harbor Cruise from Portland's Old Port

$105
Per adult
Sunset Lighthouse Harbor Cruise from Portland's Old Port
Image for Portland, Maine: Old Port Brewery & Pub Walking Tour

Portland, Maine: Old Port Brewery & Pub Walking Tour

$89
Per adult
Portland, Maine: Old Port Brewery & Pub Walking Tour
See all activities in Windham

Other vacations you might like

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