Middlebury Vacations from $750

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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.
Bluebird Cady Hill Lodge

Bluebird Cady Hill Lodge

3 out of 5
Price was $981, price is now $750 per person
$750
per person
Mar 5 - Mar 10
found 1 day ago
Roundtrip flight included
New York (JFK) to Burlington (BTV)
9.2/10 Wonderful! (611 reviews)
Room was spotless, desk was super friendly. We were late for the Stowe Stowe surf club but we will make it back.

Reviewed on Jan 13, 2026

Green Mountain Inn

Green Mountain Inn

3.5 out of 5
Stowe Village Historic District
Save 100% on your flight
Price was $1,483, price is now $1,076 per person
$1,076
per person
Mar 5 - Mar 10
found 1 day ago
Roundtrip flight included
New York (JFK) to Burlington (BTV)
9.4/10 Exceptional! (1,002 reviews)
Great little hotel in the middle of Stowe. Really enjoyed it.

Reviewed on Jan 22, 2026

AWOL Stowe

AWOL Stowe

3.5 out of 5
Save 100% on your flight
Price was $1,348, price is now $994 per person
$994
per person
Mar 5 - Mar 10
found 1 day ago
Roundtrip flight included
New York (JFK) to Burlington (BTV)
9/10 Wonderful! (204 reviews)
I cannot say enough good things about AWOL Stowe! I was visiting Stowe (and Vermont) for the first time for a short birthday trip. I stayed in the "1 King Bed Cabin" and it was SO dreamy - a little individual hotel room that was so cozy. It was nice to not share walls with neighbors, while also still feeling safe as there is plenty of people around. The staff also left a wonderful little carepackage in my room with birthday wishes. And the lobby of the hotel was exceptionally cozy and aesthetic. Check-in and out was also very easy. The *only* downside I would say to my stay is that the resort is pet friendly, so there were quite a few pet hairs on my sheets, but it was nothing a lint brush didn't fix (and I am confident the staff would have many the change in sheets had I requested it). Still, 5 out of 5 stars, and I would certainly return to AWOL Stowe and recommend it to friends in the future!

Reviewed on Jan 14, 2026

Outbound Stowe

Outbound Stowe

3.5 out of 5
Price was $1,015, price is now $770 per person
$770
per person
Mar 5 - Mar 10
found 1 day ago
Roundtrip flight included
New York (JFK) to Burlington (BTV)
9/10 Wonderful! (260 reviews)
Room in very poor condition- in particular bathroom has all fixtures falling out of wall including door handle. No fix forthcoming when I alerted Ben and Lindsey. Also, hot chocolate ran out the second day and no replacement despite asking repeatedly.

Reviewed on Jan 9, 2026

von Trapp Family Lodge & Resort

von Trapp Family Lodge & Resort

3.5 out of 5
Price was $1,344, price is now $1,057 per person
$1,057
per person
Mar 5 - Mar 10
found 1 day ago
Roundtrip flight included
New York (JFK) to Burlington (BTV)
9/10 Wonderful! (935 reviews)
Room was clean and very quiet, roomy. Enjoyed the activities at the lodge. Would recommend going

Reviewed on Jan 22, 2026

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Discover the most popular places to visit in Middlebury

Northern Vermont showing drinks or beverages

Otter Creek Brewing

4.5/5(11 reviews)

Learn about the local history of Middlebury with a stop at Otter Creek Brewing. While you're here, you can savor the top-notch restaurants.

Otter Creek Brewing
Pulp Mill Bridge, Middlebury, Vermont

Pulp Mill Covered Bridge

Find out about the history of Weybridge when you spend time at Pulp Mill Covered Bridge. While you're here, you can savor the top-notch restaurants.

Pulp Mill Covered Bridge

Middlebury College

4.5/5(108 reviews)

Enjoy the collegiate vibe when you visit Middlebury College, during your trip to Middlebury. Stroll along the riverfront or visit the cathedral while you're in the area.

Middlebury College

Middlebury Hotel Deals

Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square Middlebury VT
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $156 total per night from Feb 8 to Feb 9
$156 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
The room was clean and the customer service was top notch. Love the joining restaurant and pub. It's a historical hotel that has been well preserved. Great place to stay!

Reviewed on Jan 22, 2026

Middlebury Inn
Courtyard Middlebury

Courtyard Middlebury

3 out of 5
309 Court Street Middlebury VT
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $153 total per night from Jan 26 to Jan 27
$153 total
Jan 26 - Jan 27
Total with taxes and fees
8.8/10 Excellent! (551 reviews)
The hotel is convenient to Middlebury and comfortable, but a little worn. A limited breakfast is available for purchase (expensive) at the hotel, but there is a better breakfast place - - Rosie's - - about a 5 minute drive south of the hotel on Rt. 7.

Reviewed on Jan 5, 2026

Courtyard Middlebury
Swift House Inn

Swift House Inn

3 out of 5
57 North Pleasant Street Middlebury VT
$199 nightly
The price is $219 total per night from Feb 1 to Feb 2
$219 total
Feb 1 - Feb 2
Total with taxes and fees
9.4/10 Exceptional! (310 reviews)
We loved our 2 night stay in the Turret Room. It was cozy and quiet, the staff was so helpful, and dinner and breakfast at Jessica’s were top notch. Honestly I cannot comprehend the noise complaints on here. Unless you reside in a library or a church, I think you will find the traffic noise negligible, ...

Reviewed on Dec 1, 2025

Swift House Inn
See all 956 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 $750 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.