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.
Waldo Emerson Inn

Waldo Emerson Inn

3 out of 5
per person
Jul. 29 - Aug. 2
found 6 hours ago
Roundtrip flight included
Montreal (YUL) 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. 29 - Aug. 2
found 6 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (902 reviews)
the hotel is very beautiful, I really fell in love with the design and all the hotel's amenities and facilities, I intend to return soon

Reviewed on May 22, 2024

White Barn Inn & Spa, Auberge Resorts Collection

White Barn Inn & Spa, Auberge Resorts Collection

5 out of 5
Save 100% on your flight
per person
Jul. 29 - Aug. 2
found 6 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
9.6/10 Exceptional! (75 reviews)
Super cute hotel with classy amenities. Staff was wonderful and pay attention to detail. Drinks and food really good! Also had bikes available to ride around town.

Reviewed on Apr. 27, 2024

Hidden Pond

Hidden Pond

4 out of 5
Save 100% on your flight
per person
Jul. 29 - Aug. 2
found 6 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
8/10 Very Good! (6 reviews)
Nonantum Resort

Nonantum Resort

3.5 out of 5
per person
Jul. 29 - Aug. 2
found 6 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (636 reviews)
This place was more than what I expected. I brought my kayaks and you could launch right from the resort. It was beautiful going into the Kennebunk River then into the Atlantic. The rooms were huge and decorated tastefully. The hotel staff was accommodating and friendly. Shout out to the shuttle driver. We went down the wrong street to catch the shuttle back to the hotel. When we got to the correct shuttle stop, he was just pulling out and driving away, but saw me waving my arms and pulled over. That was so nice of him because then we would have had to wait another shuttle. The grounds were lovely, they have fire pits and cozy adirondacks for watching the water. I would definitely stay here again!!! I’m actually looking to go with my husband for our anniversary in the fall!

Reviewed on May 27, 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 $222 per night from Jun. 10 to Jun. 11
CA $222
CA $242 total
includes taxes & fees
Jun 10 - Jun 11
8.8/10 Excellent! (1,002 reviews)
"It was a comfortable stay."

Reviewed on Jun. 1, 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 $135 per night from Jun. 12 to Jun. 13
CA $135
CA $147 total
includes taxes & fees
Jun 12 - Jun 13
8.4/10 Very Good! (1,562 reviews)
"The room (and the whole facility) was super clean, the staff was great when I locked myself out of my room, and the bed was really comfy"

Reviewed on Jun. 6, 2024

Casco Bay Hotel, Ascend Hotel Collection
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 CA $291 per night from Jun. 16 to Jun. 17
CA $291
CA $331 total
includes taxes & fees
Jun 16 - Jun 17
8.4/10 Very Good! (1,056 reviews)
"All staff were super friendly and helpful. Room on 8th floor was huge, corner room, good views and could just see the ocean. We were disappointed the 15th floor bar and restaurant was closed the evening we were there. But plenty of restaurants just 10 to 20 minutes walk down to the old port area. ..."

Reviewed on Jun. 4, 2024

The Westin Portland Harborview
See all 2,880 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 $1,388. 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.