Windham Vacations from $555
Book a Hotel + Flight or Car together to unlock savings
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!
The Latest Windham Vacation Packages
- Hampton Inn Springfield South Enfield
Jan 29 - Feb 1Hampton Inn Springfield South Enfield + Flight
Enfield3 nights2.5 star property9.0/10 - Wonderful (1,000 reviews)"We love coming here it’s always so pleasant! Rooms are quiet and we live the coffee/tea 24/7!! Thank you!!"Reviewed November 1, 2026Roundtrip • Orlando (MCO) - Hartford (BDL)MCO - BDL • Nonstop BDL - MCO • 1 stop$631$555found 0 hours agoper traveler - Delamar West Hartford
Dec 29 - Jan 3Delamar West Hartford + Flight
West Hartford5 nights4.0 star property9.8/10 - Exceptional (1,000 reviews)"The staff was knowledgeable, professional, friendly and very helpful. The restaurant was excellent for dinner and the room was comfortable and lovely."Reviewed November 2, 2026Roundtrip • Tampa (TPA) - Hartford (BDL)TPA - BDL • Nonstop BDL - TPA • Nonstop$1,593$1,172found 1 day agoper traveler - Simsbury 1820 House
Dec 25 - Dec 28Simsbury 1820 House + Flight
Simsbury Center3 nights4.0 star property9.4/10 - Exceptional (1,000 reviews)"1820 was great but the room needed a new mattress. Very clean but needed a comfortable bed"Reviewed October 28, 2026Roundtrip • San Juan (SJU) - Hartford (BDL)SJU - BDL • Nonstop BDL - SJU • Nonstop$810$704found 3 hours agoper traveler - Blackberry River Inn
Jan 21 - Jan 25Blackberry River Inn + Flight
Norfolk4 nights3.0 star property9.4/10 - Exceptional (251 reviews)Roundtrip • San Juan (SJU) - Hartford (BDL)SJU - BDL • Nonstop BDL - SJU • 1 stop$676$597found 18 hours agoper traveler - Trumbull Apartments
Dec 29 - Jan 3Trumbull Apartments + Flight
Downtown Hartford5 nights3.0 star property2.0/10 - (1 review)"Terrible, worst stay ever . It was such a hassle to get in no clear instructions… never again"Reviewed September 1, 2026Roundtrip • Tampa (TPA) - Hartford (BDL)TPA - BDL • Nonstop BDL - TPA • Nonstop$1,030$916found 1 day agoper traveler
Where to stay near Windham
Norwich
Discover Norwich, a welcoming destination perfectly suited for travelers seeking a blend of excitement and relaxation. With attractions like the Mohegan Sun Arena for thrilling entertainment, the charming Mystic Seaport, and the historic Naval Submarine Base New London, there's something for every interest. Located about 14 miles away from Windham, Norwich is easily accessible by car, making it an ideal choice for a memorable getaway. Book your stay in Norwich for a delightful and diverse experience.
Mansfield
Experience the charm of Mansfield, a delightful hub for weekend getaway seekers and families who want to immerse themselves in outdoor activities and cultural experiences. From the historic University of Connecticut to the lively Harry A. Gampel Pavilion and the modern Eastern Connecticut State University, there’s plenty to explore. Conveniently located about 7 miles by car from Windham, Mansfield offers a smart choice for travelers looking to enjoy both leisure and local attractions.
South Windham
If you are an outdoor enthusiast or a couple seeking romance, look no further than South Windham, which features stunning natural scenery and a variety of attractions. This charming city is just about 2 miles from Windham and offers easy access to popular spots like the University of Connecticut and the Mohegan Sun Arena, perfect for entertainment and leisure. With its inviting atmosphere and close proximity to a lake and beach, South Windham makes for a smart choice for your next getaway.
Willimantic
Immerse yourself in Willimantic, where adventure seekers and families can easily access a blend of culture and excitement. Just a short drive from Windham, this vibrant city offers attractions like the historic University of Connecticut and the modern Eastern Connecticut State University, along with the lively Harry A. Gampel Pavilion for events. With its diverse offerings, Willimantic is a smart choice for those looking to explore unique experiences while enjoying a budget-friendly stay.
North Windham
Travelers visiting the area often choose North Windham, especially families and couples seeking close proximity to cultural experiences and outdoor adventures. With attractions like the historic University of Connecticut and the modern Eastern Connecticut State University, visitors can immerse themselves in local education and arts. The nearby urban park and nature reserve offer perfect spots for relaxation and exploration. Just about 3 miles away from Windham, North Windham makes for an excellent choice for a memorable stay.
Discover the most popular places to visit in Windham
Windham Hotel Deals
"Clean room. Staff were nice. Loud kids outside the door for a good portion of the evening."
Comfort Suites Near Casinos Norwich-Uncasville CT
Comfort Suites Near Casinos Norwich-Uncasville CT
"RUSH to the front desk and ask for Mateo because he is super helpful, kind, and has a sense of humor--Thank you Mateo! Overall, great hotel, very clean, good amenities, and a the bed was perfectly firm yet soft for a comfy night sleep. Keep up the good work."
"Always the great place to stay, staff is very friendly."
La Quinta Inn & Suites by Wyndham Norwich-Plainfield-Casino
La Quinta Inn & Suites by Wyndham Norwich-Plainfield-Casino
Frequently Asked Questions
How much does a Windham vacation package cost?
Offering excellent value package deals from $555 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.