Windham Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Windham Vacation

When you book a vacation package to Windham, you can relax and enjoy your getaway knowing that all your travel arrangements are under control. Uncover the many gems of this amazing city from your base in a neighborhood like Columbia, which is good for nature. Wondering what to do or see first during your trip to Windham? Head for major attractions such as Eastern Connecticut State University. Stop daydreaming and start traveling. Check out the wide range of options on Expedia today and finally put your Windham vacation plans in motion!

Stay near popular Windham attractions

Allanach-Wolf Woodlands

This serene 102-acre nature preserve showcases diverse ecosystems around Lake Marie and through forested trails. Explore the well-marked paths to discover scenic viewpoints and the vibrant pollinator garden.
See properties

Windham Hotel Deals

Hilltop Inn and Suites, near Foxwoods Casino

Hilltop Inn and Suites, near Foxwoods Casino

2.5 out of 5
373 Norwich Westerly Rd North Stonington CT
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $101 total per night from Aug 23 to Aug 24
$101 total
Aug 23 - Aug 24
Total with taxes and fees
7.8/10 Good! (2,838 reviews)
"Ok for price but probably wouldn’t stay there again. Beds were extremely uncomfortable. Remote for tv didn’t work ( was going to say something however staff on that night was really rude to another guest so didn’t ask). Other staff were friendly. The readers for key cards to get in room barely worked ..."

Reviewed on Aug 4, 2026

Hilltop Inn and Suites, near Foxwoods Casino
Two Trees Inn

Two Trees Inn

2.5 out of 5
240 Indiantown Rd Mashantucket CT
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $124 total per night from Aug 9 to Aug 10
$124 total
Aug 9 - Aug 10
Total with taxes and fees
8.4/10 Very Good! (160 reviews)
"It is a lovely building with some character to drive up to. The bedding and linen were the best parts of the stay. Hotel breakfast was adequate and they have a decent little bar/restaurant until 10.00 although it was so cold in there with A/C it was uninviting to eat there."

Reviewed on Aug 4, 2026

Two Trees Inn
Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich Montville CT
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $125 total per night from Sep 2 to Sep 3
$125 total
Sep 2 - Sep 3
Total with taxes and fees
9/10 Wonderful! (2,752 reviews)
"The staff was super friendly and amazing to deal with. The facility has plenty of amenities. The Samsung TV in the room was huge."

Reviewed on Aug 4, 2026

Hyatt Place Uncasville - Casino Area
See all 410 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.

Find the Best Windham Vacation Packages

Windham Essential Information

Language
English
Currency
U.S dollars
Population
23,100
Top Sights
Jorgensen Center for the Performing Arts, Lebanon Historical Society Museum and Visitors Center and Mansfield Hollow State Park

More vacations you might like

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?
Offering excellent value package deals on Expedia, you'll be surprised at how little a vacation to Windham costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Windham?
You're likely to find reduced prices and better availability in December, January and February. Take a look at our cheap Windham vacation packages and you could score some great off-season deals.
How many days is enough for Windham?
Generally, a handful of days is enough to go to the main sights during your Windham vacation. However, if you'd like to have more time to rest or go on day trips, consider extending your itinerary.
How to find the best Windham package deals?
Finding a cheap Windham package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Windham package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Windham vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and hotels individually. Better still, you can personalize your Windham getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Windham?
If you're planning an impromptu Windham vacation, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score awesome deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Windham vacation packages?
If you're like us, you love jet-setting around the world but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Windham break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.

Explore a world of travel with Expedia

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