Windham Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Windham

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 2.155.565 ₫ per night from 30 Jul to 31 Jul
2.155.565 ₫
2.479.018 ₫ total
30 Jul - 31 Jul
includes taxes & fees
8/10 Very good! (2,773 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 3 Jul 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 2.673.879 ₫ per night from 26 Jul to 27 Jul
2.673.879 ₫
3.859.729 ₫ total
26 Jul - 27 Jul
includes taxes & fees
8.8/10 Excellent! (2,676 reviews)
"The fire alarm went off during my stay. No updates were provided."

Reviewed on 4 Jul 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 4.207.520 ₫ per night from 3 Aug to 4 Aug
4.207.520 ₫
4.838.648 ₫ total
3 Aug - 4 Aug
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 4 Jul 2026

Two Trees Inn
See all 412 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

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

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

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