Search Cheap Flights to
Middlebury

Photo by Brandon Miller

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

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 , 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  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 , 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  right now, why wait?

Middlebury Flight Information
Destination airport
Middlebury
Destination airport IATA code
BDR

Last Minute Hotel Deals in Middlebury

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! (1,136 reviews)
"Nice place"

Reviewed on Oct 18, 2025

Holiday Inn Express Southington by IHG
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln, Trumbull, CT
Stay at this hotel in Trumbull. Enjoy free parking, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,003 reviews)
"Nice facility overall. A few minor issues in the room that were quickly corrected."

Reviewed on Oct 16, 2025

Trumbull Marriott Shelton
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
Stay at this 4-star 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! (1,021 reviews)
"Perfect overall"

Reviewed on Oct 18, 2025

Omni New Haven Hotel at Yale
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
Stay at this 3.5-star business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff ...
9/10 Wonderful! (1,847 reviews)
"Nice hotel. Didn’t stay long, but the king suite with pullout is spacious and comfortable. Especially with dogs. Garage is attached through a walkway across the street."

Reviewed on Oct 17, 2025

New Haven Hotel
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road, Southbury, CT
Stay at this 3-star business-friendly hotel in Southbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8/10 Very Good! (1,025 reviews)
"Quiet property close to the interstate. Nice restaurant and bar"

Reviewed on Oct 16, 2025

Wyndham Southbury
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! (1,023 reviews)
"Excellent service. Good hotel for pets"

Reviewed on Oct 18, 2025

Red Roof Inn Meriden
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane, Milford, CT
Stay at this 3-star business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,165 reviews)
"Nice"

Reviewed on Oct 16, 2025

Hyatt Place Milford / New Haven
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd, West Haven, CT
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,415 reviews)
"Clean room. Friendly staff."

Reviewed on Oct 16, 2025

Best Western Executive Hotel Of New Haven - West Haven
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.