Middlebury Vacations from $428

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Your Middlebury Vacation

Our vacation packages to Middlebury let you customize your own adventure. Tailor your journey to your interests and needs and make the most of your time in this fabulous city. You'll want to do some exploring during your trip to Middlebury. Make time for major attractions such as Middlebury College, National Museum of the Morgan Horse and UVM Morgan Horse Farm. A couple of clicks is all it takes to build the perfect Middlebury vacation on Expedia.

The Latest Middlebury vacation packages

Price found within the past 48 hours. Click for updated prices.
The Essex Resort & Spa

The Essex Resort & Spa

4 out of 5
Price was $535, price is now $428 per person
$428
per person
Jan 20 - Jan 23
found 23 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Burlington (BTV)
9/10 Wonderful! (1,011 reviews)
Had a nice little fireplace. Used it all lot. Very cozy.

Reviewed on Oct 29, 2026

Outbound Stowe

Outbound Stowe

3.5 out of 5
Price was $762, price is now $594 per person
$594
per person
Jan 20 - Jan 23
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Burlington (BTV)
9.2/10 Wonderful! (451 reviews)
We really enjoyed our time. We had a couple of issues with refills of things in our cabin by the housekeeping staff, but other than that, it was pretty perfect. The hot tub was delightful and the food and service at the restaurant was top-notch.

Reviewed on Oct 29, 2026

Club Wyndham Smugglers’ Notch Vermont

Club Wyndham Smugglers’ Notch Vermont

3.5 out of 5
Price was $897, price is now $730 per person
$730
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Burlington (BTV)
8.6/10 Excellent! (235 reviews)
This place was perfect for me and my family the kids had a blast at the pool and the fun zone

Reviewed on Oct 19, 2026

The Waitsfield Inn

The Waitsfield Inn

2.5 out of 5
Price was $1,073, price is now $882 per person
$882
per person
Dec 30 - Jan 4
found 4 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Burlington (BTV)
9/10 Wonderful! (391 reviews)
Room was comfortable and unique; I really did feel like I was staying in an old inn or house. A great change from the standard cookie-cutter chain hotel. Staff was super helpful. The lounge areas had many comfortable chairs suitable for relaxing and reading.

Reviewed on Oct 27, 2026

Hilton Garden Inn Burlington Downtown

Hilton Garden Inn Burlington Downtown

3 out of 5
Downtown Burlington
Price was $532, price is now $441 per person
$441
per person
Jan 20 - Jan 23
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Burlington (BTV)
8.8/10 Excellent! (1,003 reviews)
Overpriced

Reviewed on Oct 27, 2026

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Stay near popular Middlebury attractions

Middlebury College

9.6/10 (285 reviews)
Founded in 1800, Middlebury College offers a stunning campus where historic architecture meets the Green Mountains of Vermont. Explore the Old Chapel in this prestigious liberal arts setting.
See properties

Middlebury Hotel Deals

Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square Middlebury VT
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $158 total per night from Nov 29 to Nov 30
$158 total
Nov 29 - Nov 30
Total with taxes and fees
Middlebury Inn
Courtyard Middlebury

Courtyard Middlebury

3 out of 5
309 Court Street Middlebury VT
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $157 total per night from Nov 22 to Nov 23
$157 total
Nov 22 - Nov 23
Total with taxes and fees
Courtyard Middlebury
Swift House Inn

Swift House Inn

3 out of 5
57 North Pleasant Street Middlebury VT
$229 nightly
The price is $252 total per night from Nov 3 to Nov 4
$252 total
Nov 3 - Nov 4
Total with taxes and fees
Swift House Inn
See all 977 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.

Find the Best Middlebury Vacation Packages

Middlebury Essential Information

Language
English
Currency
U.S dollars
Population
6,600
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Branbury State Park, Otter Creek Brewing and Lincoln Peak Vineyard

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Frequently asked questions

How much does a Middlebury vacation package cost?
Offering excellent value package deals from $428 on Expedia, you'll be surprised at how little a vacation to Middlebury costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Middlebury?
If you're hoping to snag a cheap Middlebury vacation package, consider traveling in September, October and December. You'll generally find better rates on airfares and hotels during these months — perfect for a budget-friendly break.
How many days is enough for Middlebury?
Generally, a few days is ideal for a Middlebury vacation. With a carefully crafted itinerary, you can go to all the main sights such as Town Hall Theater, as well as explore some hidden gems along the way.
Is it worth booking a vacation package to Middlebury?
Middlebury is a good vacation destination with attractions like UVM Morgan Horse Farm among the many things to keep you entertained. Whether you're heading away with the family or getting away with friends, a Middlebury vacation promises fun for everyone.
How to find the best Middlebury package deals?
Use Expedia's handy filters to find some great Middlebury package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Middlebury package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Middlebury vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and hotels separately. Better still, you can customize your Middlebury getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Middlebury?
If you have your Middlebury travel dates locked in, book as early as you can to grab some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for impromptu escapes.
Does Expedia offer Book Now, Pay Later Middlebury vacation packages?
Jet off on your ideal getaway to Middlebury with help from our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until payday — we've teamed up with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to budget for your trip and snap up cheap deals before they sell out.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.