Deals on vacations and trips to Middlebury

Save when you book Middlebury, CT package deals

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Middlebury flight + hotel vacation packages

Hilton Garden Inn Hartford North/Bradley Int'l Airport
Holiday Inn Express Southington, an IHG Hotel
Simsbury Inn
Residence Inn by Marriott Hartford/Windsor
Residence Inn by Marriott Southington
Prices and availability subject to change. Additional terms may apply.

Top Middlebury hotels deals

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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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Frequently asked questions

How much are vacation packages to Middlebury?
Travelocity offers package deals to Middlebury, including flights and hotels, starting at just $580. With all that extra money, you could include some awesome tours or possibly even add a couple of extra days to your getaway.
How long should my Middlebury vacation be?
Most visitors stay in Middlebury for approximately 2 nights. That said, travel is all about checking out new things and creating unforgettable memories — why not book a couple of extra nights so you can do just that?
Where can I get the best vacation package deals for Middlebury?
Travelocity can help you lock in an unbeatable Middlebury package deal. With 400 airlines and 1,000,000 properties worldwide, we’re sure you’ll be able to craft the perfect itinerary.
Why should I purchase my Middlebury vacation bundle via Travelocity?
From our 24/7 customer care to our range of exciting destinations, we are dedicated to giving you the most unforgettable escape. All you have to do is click and book — our Price Match Guarantee will ensure you score the best deal.
Can I save money on my Middlebury car rental if I bundle it with a hotel or flight?
Bundling your hotel, car and flight into a Middlebury vacation package is the best way to land the best prices. Plus, having your own rental car gives you absolute freedom to make your way to all those big sights you’d like to check out. Sitting 70 mi away from Middlebury, Times Square is one attraction that should feature on your itinerary. Fasten your seat belt and make a day trip of it.
What is the best time of year to go to Middlebury?
If you want to avoid costly flights, big crowds and full hotels, plan your getaway outside of June, July and August. The quietest time to be in Middlebury is December, January and February. You’ll find the highest hotel prices in and the lowest in .
Which airport is best for Middlebury?
It’s likely you’ll be arriving at Bradley Intl. Airport (BDL), situated 35 mi northeast of inner Middlebury. Westchester County Airport (HPN) (45 mi away from central Middlebury) and MacArthur Airport (ISP) (50 mi away from central Middlebury) are your other choices.
What is there to do in Middlebury?
Quassy Amusement Park should be toward the top of your travel schedule. After you’ve crossed off this popular attraction, simply stroll the streets of Middlebury and find out what makes this fantastic city tick.