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Middlebury

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Middlebury Flights as Low as $126

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

Breeze Airways
Sun, Aug 10 - Wed, Aug 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$126 Roundtrip, found 9 hours ago
$126
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Sun, Aug 10 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Aug 13, priced at $126 found 9 hours ago
Avelo Airlines
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$128 Roundtrip, found 5 hours ago
$128
Roundtrip
found 5 hours ago
Select Avelo Airlines flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $128 found 5 hours ago
Breeze Airways
Sun, Aug 10 - Wed, Aug 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$131 Roundtrip, found 9 hours ago
$131
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Sun, Aug 10 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Aug 13, priced at $131 found 9 hours ago
Breeze Airways
Sun, Aug 10 - Wed, Aug 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$136 Roundtrip, found 9 hours ago
$136
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Sun, Aug 10 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Aug 13, priced at $136 found 9 hours ago
Breeze Airways
Thu, Jul 10 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$140 Roundtrip, found 9 hours ago
$140
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Jul 10 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $140 found 9 hours ago
Breeze Airways
Thu, Jul 10 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$144 Roundtrip, found 9 hours ago
$144
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Jul 10 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $144 found 9 hours ago
Breeze Airways
Thu, Jul 10 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$145 Roundtrip, found 9 hours ago
$145
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Jul 10 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $145 found 9 hours ago
Breeze Airways
Thu, Jul 10 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$151 Roundtrip, found 9 hours ago
$151
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Jul 10 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $151 found 9 hours ago
Breeze Airways
Thu, Jul 10 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$154 Roundtrip, found 9 hours ago
$154
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Jul 10 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $154 found 9 hours ago
Breeze Airways
Wed, Jul 9 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$156 Roundtrip, found 9 hours ago
$156
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $156 found 9 hours ago
Breeze Airways
Thu, Jul 10 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$158 Roundtrip, found 9 hours ago
$158
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Jul 10 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $158 found 9 hours ago
Breeze Airways
Wed, Jul 9 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$161 Roundtrip, found 9 hours ago
$161
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $161 found 9 hours ago
Breeze Airways
Thu, Jul 10 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$162 Roundtrip, found 9 hours ago
$162
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Jul 10 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $162 found 9 hours ago
Breeze Airways
Thu, Jul 10 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$163 Roundtrip, found 9 hours ago
$163
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Jul 10 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $163 found 9 hours ago
Breeze Airways
Wed, Jul 9 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$164 Roundtrip, found 9 hours ago
$164
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $164 found 9 hours ago
Breeze Airways
Wed, Jul 16 - Fri, Jul 18
PNS
Pensacola Intl.
HVN
Tweed - New Haven Regional
$644 Roundtrip, found 1 day ago
$644
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Jul 16 from Pensacola Intl. to Tweed - New Haven Regional, returning Fri, Jul 18, priced at $644 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 August, 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 $126, 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 $126 right now, why wait?

Middlebury Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$125

Last Minute Hotel Deals in Middlebury

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, a fitness center, and parking (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,604 reviews)
"Great place and the staff is top notch! It is located in an area with lots of restaurants and bars nearby. Not far from the Yale campus and all of the stores to shop at. I’d definitely stay again."

Reviewed on Jun 25, 2025

Get rates
New Haven Hotel
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.4/10 Good! (1,009 reviews)
"A great stay for our family weekend event. Carpet in the rooms need to be steamed cleaned."

Reviewed on Jun 23, 2025

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Clarion Inn
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! (1,001 reviews)
"Very comfortable room"

Reviewed on Jun 24, 2025

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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 ...
7.6/10 Good! (1,153 reviews)
"-"

Reviewed on Jun 24, 2025

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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
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
5.8/10 (1,003 reviews)
Overall very good hotel
"The stay was good. It was clean, staff very friendly. The only thing we didn't like, The elevatores were down it was very enconvenience. And my room The TV was rented not working i reported they said it will take a few minutes then i call again they said it was the weekend they had no one to look ..."

Reviewed on Jun 21, 2025

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La Quinta Inn & Suites by Wyndham New Haven
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! (1,029 reviews)
"Very clean and the staff was so kind"

Reviewed on Jun 24, 2025

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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
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 ...
8.2/10 Very Good! (1,002 reviews)
"Lovely staff very pleasant . Very clean"

Reviewed on Jun 26, 2025

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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 free parking, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.2/10 Very Good! (1,000 reviews)
"Comfy beds. Staff super nice and helpful (thanks, Aura). Great breakfast in the morning - something for everyone."

Reviewed on Jun 22, 2025

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Trumbull Marriott Shelton
See all 958 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.