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Middlebury

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Middlebury Flights as Low as $513

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

JetBlue Airways
Sat, Sep 12 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$513 Roundtrip, found 15 hours ago
$513
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Sat, Sep 12 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $513 found 15 hours ago
Alaska Airlines
Mon, Sep 14 - Thu, Sep 24
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$514 Roundtrip, found 1 day ago
$514
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Thu, Sep 24, priced at $514 found 1 day ago
JetBlue Airways
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$523 Roundtrip, found 15 hours ago
$523
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $523 found 15 hours ago
Delta
Sat, Sep 12 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$524 Roundtrip, found 16 hours ago
$524
Roundtrip
found 16 hours ago
Select Delta flight, departing Sat, Sep 12 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $524 found 16 hours ago
Alaska Airlines
Thu, Sep 10 - Thu, Sep 24
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$526 Roundtrip, found 1 day ago
$526
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Thu, Sep 10 from San Diego Intl. to Rutland Southern Vermont Regional, returning Thu, Sep 24, priced at $526 found 1 day ago
Alaska Airlines
Fri, Sep 11 - Fri, Oct 2
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$531 Roundtrip, found 16 hours ago
$531
Roundtrip
found 16 hours ago
Select Alaska Airlines flight, departing Fri, Sep 11 from San Diego Intl. to Rutland Southern Vermont Regional, returning Fri, Oct 2, priced at $531 found 16 hours ago
JetBlue Airways
Fri, Sep 11 - Fri, Oct 2
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$534 Roundtrip, found 15 hours ago
$534
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Fri, Sep 11 from San Diego Intl. to Rutland Southern Vermont Regional, returning Fri, Oct 2, priced at $534 found 15 hours ago
Delta
Wed, Sep 16 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$534 Roundtrip, found 16 hours ago
$534
Roundtrip
found 16 hours ago
Select Delta flight, departing Wed, Sep 16 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $534 found 16 hours ago
JetBlue Airways
Thu, Sep 10 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$536 Roundtrip, found 1 day ago
$536
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Sep 10 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $536 found 1 day ago
United
Fri, Sep 11 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$539 Roundtrip, found 5 days ago
$539
Roundtrip
found 5 days ago
Select United flight, departing Fri, Sep 11 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $539 found 5 days ago
JetBlue Airways
Fri, Sep 11 - Fri, Oct 2
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$540 Roundtrip, found 15 hours ago
$540
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Fri, Sep 11 from San Diego Intl. to Rutland Southern Vermont Regional, returning Fri, Oct 2, priced at $540 found 15 hours ago
Alaska Airlines
Fri, Sep 11 - Mon, Sep 28
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$541 Roundtrip, found 16 hours ago
$541
Roundtrip
found 16 hours ago
Select Alaska Airlines flight, departing Fri, Sep 11 from San Diego Intl. to Rutland Southern Vermont Regional, returning Mon, Sep 28, priced at $541 found 16 hours ago
United
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$544 Roundtrip, found 3 days ago
$544
Roundtrip
found 3 days ago
Select United flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $544 found 3 days ago
JetBlue Airways
Mon, Sep 14 - Sun, Sep 27
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$544 Roundtrip, found 16 hours ago
$544
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sun, Sep 27, priced at $544 found 16 hours ago
JetBlue Airways
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$545 Roundtrip, found 15 hours ago
$545
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $545 found 15 hours ago
American Airlines
Sat, Sep 12 - Sat, Sep 26
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$598 Roundtrip, found 5 days ago
$598
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Sep 12 from McClellan-Palomar to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $598 found 5 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 BTV 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 September, 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 Burlington Intl. 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 $513, 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 $513 right now, why wait?

Middlebury Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$513

Last Minute Hotel Deals in Middlebury

Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square Middlebury VT
Book a stay at this spa hotel in Middlebury. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,003 reviews)
"This quaint old inn has a main building, where I stayed, and two modern buildings behind it. The restaurant on the first floor was great for dinner, especially on the front veranda. This was classic old-school with stately chair and decorum. I loved the bathtub and the bed. The desk and separate ..."

Reviewed on Jul 16, 2026

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Middlebury Inn
Courtyard Middlebury

Courtyard Middlebury

3 out of 5
309 Court Street Middlebury VT
Book a stay at this business-friendly hotel in Middlebury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
9/10 Wonderful! (581 reviews)
"Great convenient property. Clean and staff was pleasant."

Reviewed on Jul 12, 2026

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Courtyard Middlebury
Swift House Inn

Swift House Inn

3 out of 5
57 North Pleasant Street Middlebury VT
Stay at this hotel in Middlebury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.6/10 Exceptional! (344 reviews)
"We stayed in one of the rooms in the Carriage House (as opposed to the Main House). It's by the road but wasn't too loud. The grounds are impeccably kept, with beautiful flowers and veggies growing everywhere. We enjoyed the buffet breakfast (shout-out to Linus for being the most friendly and welcoming ..."

Reviewed on Jul 7, 2026

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Swift House Inn
Middlebury Sweets Motel

Middlebury Sweets Motel

2.5 out of 5
1395 Rt 7 South Middlebury VT
Stay at this motel in Middlebury. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (403 reviews)
"Very well kept . Easy check in and check out. Good location. Perfect for my dog. Nice areas to walk her. Park right at your door. Fair price."

Reviewed on Jul 11, 2026

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Middlebury Sweets Motel
Trout House Village Resort

Trout House Village Resort

3 out of 5
9117 Lake Shore Dr Hague NY
Book a stay at this beach cabin in Hague. Enjoy free WiFi, free parking, and a private beach. Popular attractions Jabe Pond and Black Point Public Beach are ...
9.6/10 Exceptional! (24 reviews)
"A few things to mention: if you have an electric car, this property is not very EV-friendly. The front desk area smelled of urine and looked dirty. Overall, the property did not seem as well-maintained as expected, and I also saw roaches in our cabin. For the price they charge, I was expecting a ..."

Reviewed on Jun 20, 2026

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Trout House Village Resort
Brandon Inn

Brandon Inn

3 out of 5
20 Park Street Brandon VT
Stay at this hotel in Brandon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
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Brandon Inn
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
2551 Vermont 30N Bomoseen VT
Book a stay at this beach lodge in Bomoseen. Enjoy free parking, an outdoor pool, and a private beach. Our guests praise the restaurant and the helpful staff ...
9.4/10 Exceptional! (952 reviews)
"Great place if you like a lake. We have been coming every summer for ten years. Near by towns have nice restaurants and shopping too. Beautiful pool on the property, canoes, kayak. They also have a pontoon boat that you pay $25 an hour and get chauffeured around. We do it every year it's a beautiful ..."

Reviewed on Jul 16, 2026

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Lake Bomoseen Lodge
Circle Court Motel

Circle Court Motel

2.5 out of 5
6 Montcalm St Ticonderoga NY
Stay at this motel in Ticonderoga. Enjoy free WiFi, free parking, and cable TV channels. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (397 reviews)
"the"

Reviewed on Jul 16, 2026

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Circle Court Motel
See all 982 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.