Windham Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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!

Ready to book your vacation to Windham?

 

Choose your dates

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
The price is CA $119 per night from Jul 20 to Jul 21
CA $119
CA $137 total
Jul 20 - Jul 21
includes taxes & fees
8/10 Very good! (2,772 reviews)
"The room was clean but upon arrival our TV was falling out of the stand, reported it immediately to front desk but no one fixed it. I used a tissue box to keep it upright. Wifi was terrible, the mattresses were very lumpy and old. The ac was loud but great especially because it was 98 degrees. The ..."

Reviewed on Jul 3, 2026

Hilltop Inn and Suites, near Foxwoods Casino
Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino

Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino

3.5 out of 5
411A & 411B Norwich Westerly Road North Stonington CT
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Jul 6 to Jul 7
CA $157
CA $223 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (2,675 reviews)
"The fire alarm went off during my stay. No updates were provided."

Reviewed on Jul 4, 2026

Bellissimo Hotel, Trademark by Wyndham 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
The price is CA $225 per night from Aug 4 to Aug 5
CA $225
CA $259 total
Aug 4 - Aug 5
includes taxes & fees
8.4/10 Very good! (45 reviews)
"All I can say is very disappointing. The hotel is more for pets than that for humans. Unfortunately, I am allergic to dogs and cats and when I went down to have breakfast this morning two big dogs the size of a miniature ponies we’re in the breakfast room doesn’t get any worse than that.. I wish ..."

Reviewed on Jul 4, 2026

Two Trees Inn
See all 416 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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Stay near popular Windham attractions

Allanach-Wolf Woodlands

You can take time to visit Allanach-Wolf Woodlands during your travels to Windham.
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 season, choice of hotel and length of stay will determine how much your vacation to Windham costs.
What are the cheapest months to go to Windham?
January, February and March are great times to look for cheap Windham vacation packages. Choosing to travel in quieter months means you can typically find lower prices on hotels and flights.
How many days is enough for Windham?
With a well-organized itinerary, you can easily visit the top Windham sights in a handful of days. But if you prefer to discover lesser-known spots or take day trips, think about booking your Windham vacation for longer.
How to find the best Windham package deals?
Bagging a cheap Windham package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view 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 often lower.
Is it cheaper to book a Windham vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels separately. Better still, you can tailor your Windham getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Windham?
If you're planning an impromptu Windham vacation, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Windham?

  1. Pick your dates: What you plan to do in Windham and your preferred season can help you decide when to get away.
  2. Set a budget: Factor in expenses such as flights, food and transportation when calculating how much to put aside for your trip to Windham. Then, select a hotel that suits your budget, whether that's an economical option or a lavish retreat.
  3. Determine how many days away: Start by making a list of all the attractions and activities you'd like to experience in Windham. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Windham vacation package that brings all your bookings together.

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.