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Middlebury

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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 3 days ago
$110
Roundtrip
found 3 days 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 3 days ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$113 Roundtrip, found 3 days ago
$113
Roundtrip
found 3 days 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 3 days ago
Breeze Airways
Thu, May 14 - Sun, May 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$115 Roundtrip, found 6 hours ago
$115
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Thu, May 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 17, priced at $115 found 6 hours ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$115 Roundtrip, found 3 days ago
$115
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $115 found 3 days ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$116 Roundtrip, found 3 days ago
$116
Roundtrip
found 3 days 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 3 days ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$118 Roundtrip, found 6 hours ago
$118
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $118 found 6 hours ago
Breeze Airways
Thu, May 14 - Sun, May 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$120 Roundtrip, found 6 hours ago
$120
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Thu, May 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 17, priced at $120 found 6 hours ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$121 Roundtrip, found 3 days ago
$121
Roundtrip
found 3 days 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 3 days ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$123 Roundtrip, found 2 hours ago
$123
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $123 found 2 hours ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$125 Roundtrip, found 3 days ago
$125
Roundtrip
found 3 days 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 3 days ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$127 Roundtrip, found 2 hours ago
$127
Roundtrip
found 2 hours 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 2 hours ago
Breeze Airways
Thu, May 14 - Sun, May 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$128 Roundtrip, found 5 days ago
$128
Roundtrip
found 5 days 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 5 days ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
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, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $128 found 1 hour ago
Avelo Airlines
Thu, Jun 11 - Mon, Jun 15
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$142 Roundtrip, found 1 day ago
$142
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 $142 found 1 day ago
Avelo Airlines
Thu, Jul 9 - Sun, Jul 12
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
$200 Roundtrip, found 5 hours ago
$200
Roundtrip
found 5 hours ago
Select Avelo Airlines flight, departing Thu, Jul 9 from O'Hare Intl. to Tweed - New Haven Regional, returning Sun, Jul 12, priced at $200 found 5 hours ago
Avelo Airlines
Mon, Apr 27 - Mon, May 11
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$222 Roundtrip, found 6 days ago
$222
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Mon, Apr 27 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, May 11, priced at $222 found 6 days 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! (2,093 reviews)
Young woman at the front deak was awesome. Parking garage is nice too

Reviewed on Apr 13, 2026

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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! (1,272 reviews)
Goid complete breakfast, property was maintained , room was clean , but the hallway 2nd floor had a terrible bad fish smell! From elevators all the way down to end of hall to my room - terrible smell, i informed front desk- they dont have a clue- something fishy nasty smelling!

Reviewed on Apr 12, 2026

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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! (1,013 reviews)
The room was dusty and dirty especially the bathroom, Please be aware of noise at night! There is a nightclub across the street and you won’t be able to sleep at all. The staff are okay. Do not recommend to stay here. Please go to another Hotel.

Reviewed on Apr 13, 2026

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Omni New Haven Hotel at Yale
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! (1,295 reviews)
I've been coming to this location for a number of years. The breakfast is so so ( not that tasty). The staff was fine. Liked the floor covering change from carpet in the rooms, but the bathroom needs updating. The parking lot seems fine.

Reviewed on Apr 13, 2026

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Hyatt Place Milford / New Haven
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! (1,010 reviews)
no hot tub. listing lied

Reviewed on Apr 13, 2026

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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! (1,104 reviews)
Had cockroaches in my room

Reviewed on Apr 13, 2026

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Hilton Garden Inn Shelton
Courtyard by Marriott New Haven Orange-Milford

Courtyard by Marriott New Haven Orange-Milford

3 out of 5
136 Marsh Hill Rd Orange CT
Book a stay at this business-friendly hotel in Orange. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very Good! (1,003 reviews)
The TV didn't work, the wifi was in and out, property basic upkeep was deficient including plugs, lighting fixtures pulling from wall. The shouwer handle also pulled out from the fixture which a simple tightening of a set screw would have solved.

Reviewed on Apr 12, 2026

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Courtyard by Marriott New Haven Orange-Milford
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! (1,183 reviews)
Customer service was extremely poor. Rashheda was fabulous getting me in early, but that’s it. The amenities were terrible.. one pack of coffee, one sugar and one creamer and that’s all you get in your room. Are you kidding me? You turn on the heater or the air conditioner it’s so loud that you have ...

Reviewed on Apr 13, 2026

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Courtyard by Marriott Waterbury Downtown
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.