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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

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 ...
9.2/10 Wonderful! (2,150 reviews)
"Thin walls with horrible noise blocking. Otherwise is ok."

Reviewed on Jun 1, 2026

New Haven Hotel
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! (1,321 reviews)
"Great stay"

Reviewed on Jun 3, 2026

Holiday Inn Express Southington by IHG
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 breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,017 reviews)
"My recent stay at the Omni New Haven was truly excellent. The hotel reception staff were super helpful and amazing at both check in and checkout, the room was super clean and well appointed and breakfast was delicious. The Omni will be my hotel choice whenever traveling to New Haven."

Reviewed on Jun 1, 2026

Omni New Haven Hotel at Yale
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 ...
8/10 Very Good! (1,634 reviews)
"Honestly the breakfast was way more than an average hotel, sounds silly but they had your standard stuff plus an entire assortment of donuts and pastries which I was not expecting, pool area was nice as well."

Reviewed on Jun 3, 2026

Best Western Executive Hotel Of New Haven - West Haven
La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
400 Sargent Dr New Haven CT
Book a stay at this business-friendly hotel in New Haven. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
6/10 (1,268 reviews)
"Not a bad place. We had a pull out and they didn’t have extra pillows which is somewhat weird. Breakfast had good options"

Reviewed on Jun 2, 2026

La Quinta Inn & Suites by Wyndham New Haven
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3 out of 5
63 Grand St Waterbury CT
Stay at this hotel in Waterbury. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (1,232 reviews)
"Solo traveler I went for 4 days to hang out in CT. This location was close to what I needed. Staff are nice and property is definitely 3 star headed towards 2 stars .. but it gets the job done for the stay. There are no microwaves You can park in the garage for free if you don’t tell the front desk ..."

Reviewed on Jun 2, 2026

Courtyard by Marriott Waterbury Downtown
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 ...
8.6/10 Excellent! (1,315 reviews)
"Everything was great. It was a peaceful weekend for me."

Reviewed on May 31, 2026

Hyatt Place Milford / New Haven
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd Shelton CT
Book a stay at this business-friendly hotel in Shelton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8/10 Very Good! (1,135 reviews)
"Requested every day cleaning told ok then Sunday morning found a letter saying they don't clean on Sunday cleaning lady said she will clean that never happened"

Reviewed on Jun 3, 2026

Hilton Garden Inn Shelton
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.