Search Cheap Flights to
Middlebury

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Middlebury Flights as Low as $110

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

Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$110 Roundtrip, found 1 hour ago
$110
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $110 found 1 hour ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$113 Roundtrip, found 1 hour ago
$113
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $113 found 1 hour ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$116 Roundtrip, found 1 hour ago
$116
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $116 found 1 hour ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$121 Roundtrip, found 1 hour ago
$121
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $121 found 1 hour ago
Breeze Airways
Thu, May 14 - Sun, May 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$123 Roundtrip, found 1 hour ago
$123
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, May 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 17, priced at $123 found 1 hour ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$125 Roundtrip, found 1 hour ago
$125
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $125 found 1 hour ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $127 found 4 days ago
Breeze Airways
Thu, May 14 - Sun, May 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$128 Roundtrip, found 1 hour ago
$128
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, May 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 17, priced at $128 found 1 hour ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$132 Roundtrip, found 5 days ago
$132
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $132 found 5 days ago
Breeze Airways
Thu, May 14 - Sun, May 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$133 Roundtrip, found 2 days ago
$133
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, May 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 17, priced at $133 found 2 days ago
Avelo Airlines
Mon, Apr 13 - Wed, Apr 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Apr 22, priced at $138 found 1 day ago
Avelo Airlines
Thu, Jun 11 - Mon, Jun 15
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Thu, Jun 11 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Jun 15, priced at $163 found 1 day ago
Avelo Airlines
Mon, Apr 13 - Thu, Apr 23
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$172 Roundtrip, found 2 days ago
$172
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Thu, Apr 23, priced at $172 found 2 days ago
Breeze Airways
Mon, Apr 13 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$181 Roundtrip, found 1 day ago
$181
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $181 found 1 day ago
Avelo Airlines
Mon, Apr 13 - Sun, Apr 19
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$182 Roundtrip, found 3 days ago
$182
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Sun, Apr 19, priced at $182 found 3 days ago
Avelo Airlines
Thu, Apr 30 - Sat, May 9
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$240 Roundtrip, found 1 day ago
$240
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Thu, Apr 30 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, May 9, priced at $240 found 1 day ago

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 $110, 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 $110 right now, why wait?

Middlebury Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$110

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! (2,076 reviews)
comfortable beds, clean rooms and general areas, helpful staff, very close to Yale University

Reviewed on Apr 8, 2026

Get rates
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! (1,263 reviews)
Clean lobby and great hotel staff. Hall way carpets could use a clean

Reviewed on Apr 8, 2026

Get rates
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 ...
8.6/10 Excellent! (1,291 reviews)
The breakfast is excellent. A lot of choices. The room is spacious and clean. The staff are nice.

Reviewed on Apr 6, 2026

Get rates
Hyatt Place Milford / New Haven
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! (1,005 reviews)
I had a little bit of a complicated reservation because I had reserved one night several months ago and about two weeks before our trip we decided to stay a second night. I was unable to modify my reservation so I just booked a second. I called the Omni to see if we could tie the two reservations ...

Reviewed on Apr 8, 2026

Get rates
Omni New Haven Hotel at Yale
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Stay at this hotel in Trumbull. Enjoy an outdoor pool, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
8/10 Very Good! (1,002 reviews)
The room was eh at best… our mattress was coming apart, the sheets were too small for the mattress & didn’t fit, there were stains on the ill fitting bed skirts, there was no garbage pail in the room, only the bathroom, the wood flooring in the vanity area was water logged and sagging, the sink didn’t ...

Reviewed on Apr 7, 2026

Get rates
Trumbull Marriott Shelton
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! (1,095 reviews)
Quiet Clean Excellent food...5 stars all around.

Reviewed on Apr 6, 2026

Get rates
Hilton Garden Inn Shelton
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! (1,170 reviews)
Staff were outstanding making the stay better than expected.

Reviewed on Apr 5, 2026

Get rates
Courtyard by Marriott Waterbury Downtown
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! (1,576 reviews)
Our room was clean and the staff friendly and helpful. The only issue we had was a leaky refrigerator. Other than that, the hot breakfast was tasty and the location easy to find, since it's right off the highway.

Reviewed on Apr 7, 2026

Get rates
Best Western Executive Hotel Of New Haven - West Haven
See all 1,091 properties in Middlebury
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.