Middlebury Vacations from $289
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Your Middlebury Vacation
You'll find plenty to like about Middlebury, from its rich history to its cultural experiences. When you're ready to say hello to this fascinating city, our Middlebury vacation packages are calling your name. A trip to Middlebury is a terrific opportunity to sightsee. Be sure to visit popular attractions like Quassy Amusement Park, Palace Theatre and Brass Mill Center. No matter your travel plans or budget, organizing your ultimate tailored Middlebury vacation is a breeze with Expedia.
The Latest Middlebury Vacation Packages
- Pier Blue Inn Old Saybrook - Essex
Dec 11 - Dec 13Pier Blue Inn Old Saybrook - Essex + Flight
Saybrook Manor2 nights2.0 star property8.0/10 - Very good (1,007 reviews)Roundtrip • San Juan (SJU) - New Haven (HVN)SJU - BDL • Nonstop BDL - SJU • Nonstop$346$289found 19 hours agoper traveler - Beechmont - Perfect for Family Retreat!
Dec 30 - Jan 2Beechmont - Perfect for Family Retreat! + Flight
North End3 nights5.0 star propertyRoundtrip • Miami (MIA) - New Haven (HVN)FLL - HVN • Nonstop HVN - FLL • Nonstop$2,403$1,465found 17 hours agoper traveler - Heritage Hotel, Golf & Conference Center
Dec 30 - Jan 2Heritage Hotel, Golf & Conference Center + Flight
Southbury3 nights3.5 star property8.4/10 - Very good (1,000 reviews)Roundtrip • Miami (MIA) - New Haven (HVN)MIA - EWR • Nonstop EWR - MIA • Nonstop$629$515found 1 day agoper traveler - Landing Apartments Downtown New Haven
Dec 30 - Jan 2Landing Apartments Downtown New Haven + Flight
Downtown New Haven3 nights3.0 star propertyRoundtrip • Miami (MIA) - New Haven (HVN)MIA - EWR • Nonstop EWR - MIA • Nonstop$965$805found 1 day agoper traveler - Omni New Haven Hotel at Yale
Dec 30 - Jan 2Omni New Haven Hotel at Yale + Flight
Downtown New Haven3 nights4.0 star property8.8/10 - Excellent (1,120 reviews)Roundtrip • Miami (MIA) - New Haven (HVN)MIA - EWR • Nonstop EWR - MIA • Nonstop$731$620found 1 day agoper traveler
Where to stay in and around Middlebury
Waterbury
Discover Waterbury, a vibrant city perfect for family travelers seeking a blend of outdoor adventures and urban experiences. With attractions like the thrilling Lake Compounce amusement park and the historic Quinnipiac University, there's plenty to explore. Waterbury is also home to the impressive City Hall and various educational venues, making it an engaging destination year-round. Located about 5 miles by car from Middlebury, Waterbury is an excellent choice for your stay, offering a unique mix of activities for everyone.
Southington
Experience the charm of Southington, an excellent hub for families and adventure-seekers who want a mix of excitement and relaxation. This vibrant city features attractions like Lake Compounce amusement park and Quinnipiac University, perfect for creating lasting memories. With a variety of outdoor activities and educational venues, Southington offers something for everyone. Located about 15 miles by car from Middlebury, it's a smart choice for your stay, balancing convenience with delightful experiences.
Naugatuck
If you are a traveler seeking a blend of outdoor adventure and family-friendly activities, look no further than Naugatuck, Connecticut. This vibrant city offers easy access to attractions like Yale University, where you can immerse yourself in history, and the scenic Beacon Falls Town Recreation Field, perfect for a day outdoors. With Naugatuck located about 5 miles from Middlebury, it serves as an ideal base for exploring the area. Choosing Naugatuck for your stay ensures a memorable and diverse experience.
Southbury
Southbury stands out as a prime spot for travelers interested in outdoor adventures and family fun. This charming city offers easy access to attractions like Quassy Amusement Park, Southford Falls State Park, and the scenic Candlewood Lake, making it a delightful destination for both couples and families. With its proximity at about 6 miles from Middlebury, Southbury is a smart choice for your stay, providing a perfect blend of recreation and relaxation.
Woodbury
Travelers visiting the area often choose Woodbury, especially families and those seeking a weekend getaway, drawn by its charming blend of outdoor activities and local attractions. With access to Quassy Amusement Park for fun-filled days, the scenic Hollow Park for relaxation, and the serene Abbey of Regina Laudis for a touch of tranquility, Woodbury provides a delightful escape. Located about 4 miles from Middlebury, it offers a smart choice for accommodations, ensuring a memorable stay in Connecticut.
Discover the most popular places to visit in Middlebury
Middlebury Hotel Deals
Courtyard by Marriott Waterbury Downtown
Courtyard by Marriott Waterbury Downtown
Heritage Hotel, Golf & Conference Center
Heritage Hotel, Golf & Conference Center
"The room had a strong mildew smell that caused me to be congested when in the room."
Comfort Inn Naugatuck-Shelton, CT
Comfort Inn Naugatuck-Shelton, CT"It was a nice stay, but the front desk staff needs to stand up when registering guests."
Holiday Inn Cheshire - Southington by IHG
Holiday Inn Cheshire - Southington by IHGFrequently Asked Questions
How much does a Middlebury vacation package cost?
You can grab a vacation package to this top destination from $289 on Expedia. However, how much your vacation to Middlebury costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Middlebury?
You're likely to find lower prices and better availability in December, January and February. Take a look at our cheap Middlebury vacation packages and you could get some excellent off-season deals.
How many days is enough for Middlebury?
With a well-planned schedule, you can easily visit the most popular Middlebury sights in a handful of days. But if you want to venture off the beaten track or take day trips, consider booking your Middlebury vacation for longer.
How to find the best Middlebury package deals?
Landing a cheap Middlebury package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Middlebury package deals. Want a simple trick to get 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 Middlebury vacation as a package?
You can enjoy significant savings on your next Middlebury getaway by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Middlebury?
If you have your Middlebury vacation dates finalized, book as early as you can to score some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Middlebury vacation packages?
If you're anything 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 the help of online lender Affirm, you can spread the overall cost of your Middlebury vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.