Windham Vacation Packages

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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.

Top Windham Vacation Deals

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

River View Resort

2.5 out of 5
Save 100% on your flight
per person
Jul. 15 - Jul. 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Jul. 22 - Jul. 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (1,192 reviews)
Loved the overall vibe and service!

Reviewed on May 31, 2024

Ogunquit Hotel & Suites

Ogunquit Hotel & Suites

2 out of 5
Save 100% on your flight
per person
Jul. 15 - Jul. 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.6/10 Excellent! (1,002 reviews)
Is Very close to the town with great options in restaurants and shopping places.

Reviewed on May 27, 2024

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
per person
Jul. 22 - Jul. 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (648 reviews)
It was really conveniently located with a great rooftop bar.

Reviewed on May 28, 2024

The Press Hotel, Marriott Autograph Collection

The Press Hotel, Marriott Autograph Collection

4 out of 5
Downtown Portland
per person
Jul. 22 - Jul. 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.6/10 Exceptional! (858 reviews)
AMAZING customer service!

Reviewed on May 17, 2024

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 refundableReserve now, pay when you stay
The price is CA $220 per night from Jun. 2 to Jun. 3
CA $220
CA $239 total
includes taxes & fees
Jun 2 - Jun 3
8.8/10 Excellent! (999 reviews)
"Close to little sebago, shopping and food."

Reviewed on May 28, 2024

Microtel Inn & Suites By Wyndham Windham
Casco Bay Hotel, Ascend Hotel Collection
Casco Bay Hotel, Ascend Hotel Collection
3.5 out of 5
80 John Roberts Rd., South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Jun. 2 to Jun. 3
CA $121
CA $132 total
includes taxes & fees
Jun 2 - Jun 3
8.4/10 Very Good! (1,530 reviews)
"No complaints. Reception was nice and check in was fast and easy. The room was clean and bed were comfortable."

Reviewed on May 31, 2024

Casco Bay Hotel, Ascend Hotel Collection
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 CA $326 per night from Jun. 2 to Jun. 3
CA $326
CA $412 total
includes taxes & fees
Jun 2 - Jun 3
9/10 Wonderful! (1,191 reviews)
"Nice building in a pleasant neighborhood. Comfortable bed. Convenient coffee maker. Helpful valet parking."

Reviewed on May 29, 2024

Portland Harbor Hotel
See all 2,907 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Windham vacation package cost?
From just CA $985. 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

5/5(1 review)

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

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

CA $198
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

CA $122
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

CA $121
Per adult
Portland, Maine: Old Port Brewery & Pub Walking Tour
See all activities in Windham

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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.