Windham Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Windham
Hilltop Inn and Suites, near Foxwoods Casino
373 Norwich Westerly Rd North Stonington CT
Fully refundableReserve now, pay when you stay
S$130
16 Aug - 17 Aug
includes taxes & fees
7.8/10 Good! (2,867 reviews)
"I canceled a night weeks before arriving. They made me pay and wait for careful d. I’ve been fighting the $200 charge for three weeks. The front desk guy is rude"
Reviewed on 10 Aug, 2026
Two Trees Inn
240 Indiantown Rd Mashantucket CT
Fully refundableReserve now, pay when you stay
S$154
16 Aug - 17 Aug
includes taxes & fees
8.4/10 Very good! (196 reviews)
"Check in was at 4pm. We arrived at 3:50pm and was told they had no time frame when our room would be ready. They said it was because they were busy the night prior…..not an excuse when I have a reservation booked and plans to attend. Didn’t get a room for almost 2 hours after the check in time. That ..."
Reviewed on 10 Aug, 2026
Hyatt Place Uncasville - Casino Area
2049 Norwich Montville CT
Fully refundableReserve now, pay when you stay
S$154
9 Sept - 10 Sept
includes taxes & fees
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
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.
Windham Free Library
Connecticut's smallest freestanding library houses the Windham Bacchus, a wooden figure carved by British prisoners in 1776. Browse historical artefacts in this intimate Greek Revival building.
Gauthier Field
This quiet Connecticut park offers green spaces near historical sites connected to Rochambeau's Army. Bring a picnic and comfortable shoes to enjoy this peaceful local retreat with historical significance.
Cloutier Memorial Forest
This serene 105-acre nature reserve honours George Cloutier, WWII veteran and forester. Explore woodland trails, observe local wildlife, and find tranquility at two small ponds nestled within the Connecticut landscape.
Edward Waldo House Museum
Step back in time at this 1715 colonial house where the Waldo family lived for 250 years. Explore three floors of original features and period furnishings during monthly summer open houses.
Frequently asked questions
How much does a Windham holiday package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday to Windham costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Windham?
January, February and March are the best times to search for cheap Windham holiday packages. Choosing to travel in quieter months means you can generally find lower prices on hotels and flights.
How many days is enough for Windham?
The ideal length for your Windham holiday depends on what you'd like to see and do. Usually, a few days to a week will give you time to tick off all the major sights and discover some hidden treasures along the way.
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 holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking flights and hotels individually. Better still, you can personalise 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 holiday package to Windham?
If you're planning an impromptu Windham holiday, 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.
How to plan a trip to Windham?
- Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to go to Windham.
- Budget wisely: Besides the price of your stay, you'll need to factor in other expenses. These include transportation, food and flights. Also, put aside a little extra for unexpected expenses that may arise during your trip to Windham.
- Decide how long to go away for: Now that you're more familiar with Windham, you can figure out the perfect length of your holiday. Create a draft plan and give yourself enough time to cover everything you want to do.
- Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customised Windham holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
