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.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
7.8/10 Good! (1,056 reviews)
I would have like to have the hotel provide a continental breakfast. There was a restaurant attached to the hotel called "Stacks" that was a rip off they charged me for the milk in my tea.

Reviewed on Aug. 7, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
Great option in Old Port. Very convenient to dining, shopping and boat tours. You can walk to everything. Courtyard was lovely in the evening for cocktails around the firepit. Would definitely recommend!

Reviewed on Aug. 7, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
per person
Oct 17 - Oct 22
found 2 hours ago
Roundtrip flight included
Hamilton (YHM) to Portland (PWM)
9.4/10 Exceptional! (1,005 reviews)
Incredible views and very confortable rooms

Reviewed on Aug. 6, 2025

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (856 reviews)
We enjoyed our visit

Reviewed on Aug. 7, 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (598 reviews)
The breakfast each more was varied and delicious. There are bikes on the property which are great to ride around town

Reviewed on Jul. 29, 2025

Ready to book your vacation to Windham?

 

Choose your dates

Windham Hotel Deals

Dormir

Dormir

3 out of 5
965 Roosevelt Trail, Windham, ME
Fully refundableReserve now, pay when you stay
The price is CA $317 per night from Aug 13 to Aug 14
CA $317
CA $346 total
Aug 13 - Aug 14
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"I like the cleanliness. I do wish that for the price, room cleaning/replenishing towels, was available. Currently have to bring dirty towels down, in order to get clean ones."

Reviewed on Aug. 5, 2025

Dormir
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from Aug 24 to Aug 25
CA $160
CA $174 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,126 reviews)
Pleasantly surprised!
"After I booked the room, I started to read some of the reviews and instantly began to regret my decision. I didn’t have time to refund it so we took a chance. I’m glad we did! I’m not sure what all the fuss was about. I saw no bugs. I thoroughly checked. Albeit the room wasn’t immaculate. Housecleaning ..."

Reviewed on Aug. 6, 2025

Days Inn by Wyndham Airport/Maine Mall
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is CA $147 per night from Aug 17 to Aug 18
CA $147
CA $160 total
Aug 17 - Aug 18
includes taxes & fees
7.4/10 Good! (117 reviews)
"They did not have my accessible room ready when I arrived at 3 pm. The WiFi setup was very clunky and only partial worked."

Reviewed on Aug. 2, 2025

Germaine Inn South Portland
See all 3,324 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.
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What to do in Windham

Port City Light Cruise

Port City Lights Cruise

CA $53
per adult
100% of travellers recommend
Port City Lights Cruise
Portland: Maine Lighthouses Sightseeing Cruise with Drinks

Portland: Maine Lighthouses Sightseeing Cruise with Drinks

CA $95
per adult
Portland: Maine Lighthouses Sightseeing Cruise with Drinks
Portland: Sightseeing Cruise to Portland Head Light

Portland: Sightseeing Cruise to Portland Head Light

CA $49
per adult
98% of travellers recommend
Portland: Sightseeing Cruise to Portland Head Light
See all activities in Windham

Frequently asked questions

How much does a Windham vacation package cost?
You'll find cheap prices from CA $937 on Expedia for your Windham getaway. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Windham costs.
What are the cheapest months to go to Windham?
You can generally find lower prices and greater availability in January, February and November. Take a look at our cheap Windham vacation packages and you could score some excellent off-season deals.
How many days is enough for Windham?
With a well-planned schedule, you can easily hit the main Windham sights in a few days. But if you prefer to venture off the beaten track or go on day trips, think about booking your Windham vacation for longer.
How to find the best Windham package deals?
Start your search for a Windham package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Windham package deal straight away, just switch up 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 off to a flying start.
Is it cheaper to book a Windham vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Windham vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Windham?
If you have your Windham vacation dates locked in, book as early as you can to bag some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Windham?

  1. Choose your dates: What you plan to do in Windham and your preferred season will help you decide when to go.
  2. Work out your budget: Ensure you have enough money to cover everything from dining out and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to Windham.
  3. Decide how long to go for: Now that you know more about Windham, you can work out the ideal length of your vacation. Create a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Windham vacation package that brings all your bookings together.

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