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Middlebury

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Middlebury Flights as Low as $93

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
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Avelo Airlines
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Avelo Airlines
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways

Cheap Flights to Middlebury

Fall in love at first flight with your vacation to Middlebury by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Middlebury on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Middlebury, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Middlebury

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Middlebury with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the BDR airport.

What is the cheapest month to fly to Middlebury?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Middlebury are in April, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Middlebury?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Middlebury.

What airport is best to fly into Middlebury?

When you’re planning your trip to Middlebury, convenience is the name of the game. Luckily, Middlebury Waterbury - Oxford Airport is nearby so you can deplane and get going on checking off everything on your Middlebury must-do list.

How much are flights to Middlebury?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Middlebury on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $93, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Middlebury?

The trick to saving a stack of cash on your flight to Middlebury? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $93 right now, why wait?

Middlebury Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$92

Last Minute Hotel Deals in Middlebury

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
9/10 Wonderful! (2,028 reviews)
Great staff. Rooms are clean but not special. Location is spectacular.

Reviewed on Feb 18, 2026

New Haven Hotel
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street New Haven CT
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,016 reviews)
Very modern new clean facilities

Reviewed on Feb 16, 2026

Cambria Hotel New Haven University Area
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St New Haven CT
Book a stay at this business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,006 reviews)
Great

Reviewed on Feb 16, 2026

Omni New Haven Hotel at Yale
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

2.5 out of 5
1 Batterson Park Rd Farmington CT
Book a stay at this business-friendly hotel in Farmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7.8/10 Good! (999 reviews)
Everything was good

Reviewed on Feb 15, 2026

Extended Stay America Suites Hartford Farmington
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,217 reviews)
Great hot breakfast, quiet rooms. Overall looks nicely renovated, but there are some minor defects

Reviewed on Feb 13, 2026

Holiday Inn Express Southington by IHG
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane Milford CT
Book a stay at this business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (1,250 reviews)
Great

Reviewed on Feb 18, 2026

Hyatt Place Milford / New Haven
Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven

3 out of 5
30 Frontage Rd East Haven CT
Book a stay at this business-friendly inn in East Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Shoreline Trolley Museum and ...
9.4/10 Exceptional! (489 reviews)
I had never stayed in a Home2 Suites location, so I had no idea what to expect. The room was spacious and clean. They had a great breakfast buffet area with tasty food options. The beds were super comfortable! I will definitely stay at a Home2 Suites again!

Reviewed on Feb 16, 2026

Home2 Suites by Hilton East Haven New Haven
Red Roof Inn Meriden

Red Roof Inn Meriden

2 out of 5
10 Bee St Meriden CT
Book a stay at this business-friendly hotel in Meriden. Enjoy free WiFi, free parking, and a health club. Our guests praise the helpful staff and the clean rooms ...
7.4/10 Good! (1,000 reviews)
Room was very clean!

Reviewed on Jan 25, 2026

Red Roof Inn Meriden
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.