Windham Vacations

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Find the Best Windham Vacation Packages

Windham Hotel Deals

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundable
The price is AEDĀ 334 per night from Dec 6 to Dec 7
AEDĀ 334
AEDĀ 369 total
6 Dec - 7 Dec
includes taxes & fees
9/10 Wonderful! (1,012 reviews)
"Nice property. High parking fees"

Reviewed on 11 November 2026

The Westin Portland Harborview
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
The price is AEDĀ 278 per night from Nov 18 to Nov 19
AEDĀ 278
AEDĀ 307 total
18 Nov - 19 Nov
includes taxes & fees
8.2/10 Very Good! (1,875 reviews)
"This is a place I stay in Portland when I want to a place to crash after a busy day at a affordable price. The staff are wonderful and helpful. The shuttle service is great. The hotel is just old and needs to be renovated which I believe is planned."

Reviewed on 11 November 2026

Clarion Hotel Portland Airport ME
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
The price is AEDĀ 297 per night from Nov 23 to Nov 24
AEDĀ 297
AEDĀ 329 total
23 Nov - 24 Nov
includes taxes & fees
Fireside Inn & Suites Portland
See all 3,149 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.

Stay near popular Windham attractions

beach near Boathouse Beach Lane

Why not spend a lazy afternoon at beach near Boathouse Beach Lane during your trip to Windham? Stroll along this family-friendly area's lakeside, or simply enjoy its restaurants.
See properties

Frequently asked questions

How much does a Windham vacation package cost?
You'll find cheap prices 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 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 traveling 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.