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Middlebury

Name: Courtyard by Marriott Waterbury Downtown
Rating: 8.4

Either off access road at the end of Old Waterbury Rd, or Umberfield Rd. Abandoned in the woods near I 84 and power lines overhead.

Photo by Brandon Miller

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Middlebury Flights as Low as $483

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

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One way

Roundtrip

Sat, May 17 - Mon, Jun 9

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$483

Roundtrip

found 1 day ago

Sat, May 17 - Fri, Jun 6

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$493

Roundtrip

found 1 day ago

Thu, May 15 - Fri, Jun 6

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$493

Roundtrip

found 1 day ago

Sat, May 17 - Mon, Jun 9

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$502

Roundtrip

found 3 hours ago

Mon, May 12 - Fri, Jun 6

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$509

Roundtrip

found 1 day ago

Thu, May 15 - Mon, Jun 9

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$512

Roundtrip

found 3 hours ago

Sat, May 17 - Fri, Jun 6

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$521

Roundtrip

found 3 hours ago

Thu, May 15 - Thu, Jun 5

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$522

Roundtrip

found 3 hours ago

Fri, May 16 - Mon, Jun 9

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$529

Roundtrip

found 3 hours ago

Thu, May 15 - Fri, Jun 6

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$531

Roundtrip

found 3 hours ago

Sat, May 17 - Sun, Jun 8

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$531

Roundtrip

found 3 hours ago

Fri, May 16 - Thu, Jun 5

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$539

Roundtrip

found 3 hours ago

Wed, May 14 - Mon, Jun 9

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$540

Roundtrip

found 1 day ago

Thu, May 15 - Sun, Jun 8

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$541

Roundtrip

found 3 hours ago

Fri, May 16 - Fri, Jun 6

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$548

Roundtrip

found 3 hours ago

Wed, May 14 - Mon, Jun 9

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$550

Roundtrip

found 3 hours 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.

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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 May, 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 $483, 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 $483 right now, why wait?

Last Minute Hotel Deals in Middlebury

New Haven Hotel

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! (1,530 reviews)

"Great location, excellent gym, great service."

Reviewed on May 9, 2025

Get rates

Clarion Inn

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! (1,001 reviews)

"Awsome"

Reviewed on May 6, 2025

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Holiday Inn Express Southington by IHG

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! (1,012 reviews)

"Staff was extremely helpful and efficient. Room was very clean.. easy parking, easy access to dining facilities and highways.. will definitely stay here again"

Reviewed on May 7, 2025

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Cambria Hotel New Haven University Area

20 Dwight Street, New Haven, CT

Stay at this 3-star business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...

8.8/10 Excellent! (728 reviews)

"Great hotel stay!"

Reviewed on May 7, 2025

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Omni New Haven Hotel at Yale

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! (1,003 reviews)

"Omni staff were very nice."

Reviewed on May 8, 2025

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Hyatt Place Milford / New Haven

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! (1,009 reviews)

"Eli and Jarrell were accommodating and friendly from start to finish. They were funny, but professional - informative, attentive, and courteous to every single person that passed through, including the dogs. I was extremely impressed."

Reviewed on May 8, 2025

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Trumbull Marriott Shelton

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! (1,002 reviews)

"The only thing i would change is i wish they had a starbucks inside but target is a 5 minute walk away with a starbucks!"

Reviewed on May 8, 2025

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Courtyard by Marriott Waterbury Downtown

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! (1,003 reviews)

"Room was clean, right off the highway without hearing the highway."

Reviewed on May 7, 2025

Get rates

See all 967 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.

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