Middlebury Vacations from ￥202,394

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The Latest Middlebury Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Outbound Stowe

Outbound Stowe

3.5 out of 5
per person
Feb 24 - Mar 1
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Burlington (BTV)
9/10 Wonderful! (78 reviews)
This was such a fantastic resort! Cool, midmodern meets " ski lodge" vibe; friendly, helpful staff, clean facilities abd great location!!!

Reviewed on Jan 18, 2025

Club Wyndham Smugglers’ Notch Vermont

Club Wyndham Smugglers’ Notch Vermont

3.5 out of 5
per person
Feb 24 - Mar 1
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Burlington (BTV)
8.4/10 Very Good! (162 reviews)
The best place for families, we love it!!

Reviewed on Jan 5, 2025

Smugglers' Notch Resort

Smugglers' Notch Resort

3 out of 5
per person
Feb 24 - Mar 1
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Burlington (BTV)
8/10 Very Good! (107 reviews)
Wish we could have stayed longer!

Reviewed on Jan 7, 2025

Field Guide Lodge

Field Guide Lodge

3.5 out of 5
per person
Feb 24 - Mar 1
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Burlington (BTV)
9.2/10 Wonderful! (1,001 reviews)
Very nice property and friendly staff!

Reviewed on Jan 19, 2025

Green Mountain Inn

Green Mountain Inn

3.5 out of 5
per person
Feb 24 - Mar 1
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Burlington (BTV)
9.4/10 Exceptional! (1,005 reviews)
This is a quintessential inn located in the heart of the lovely Stowe! Where to start. Excellent room, quaint but updated. Lots of space and the gas fireplace really was wonderful. Gorgeous indoor/outdoor hot tub and spa option. We loved the hot tub outside after a day skiing. Location is unbeatable. In the heart of Stowe, lots going on and a good restaurant within it too. The shuttle to the mountain is right across the street making the trip to Stowe to ski so easy. Stowe is really a lovely town and this inn made our experience that much better.

Reviewed on Jan 21, 2025

Find the Best Middlebury Vacation Packages

Middlebury Hotel Deals

Middlebury Inn
Middlebury Inn
3 out of 5
14 Court Square, Middlebury, VT
The price is ￥22,427 per night from Jan 29 to Jan 30
￥22,427
￥24,670 total
includes taxes & fees
Jan 29 - Jan 30
8.8/10 Excellent! (1,002 reviews)
"Very gracious accommodations. Old world charm."

Reviewed on Jan 20, 2025

Middlebury Inn
Courtyard Middlebury
Courtyard Middlebury
3 out of 5
309 Court Street, US Rt 7 / Historic Ethan Allen Hwy, Middlebury, VT
Fully refundableReserve now, pay when you stay
The price is ￥21,580 per night from Jan 23 to Jan 24
￥21,580
￥23,738 total
includes taxes & fees
Jan 23 - Jan 24
8.8/10 Excellent! (490 reviews)
"Very conveniently located and easy parking. While somewhat understaffed, the staff were friendly and as responsive as they could be. Our fireplace switch didn't work but they came and tried to fix it. When our son decided to stay with us in our room, they easily accommodated us with a rollaway bed. ..."

Reviewed on Jan 13, 2025

Courtyard Middlebury
Waybury Inn
Waybury Inn
3.5 out of 5
457 East Main Street, Middlebury, VT
9.2/10 Wonderful! (69 reviews)
"Online it says it has an EV charging station but it doesn't. But not too much of a setback otherwise the place was very cute and hospitable! Great Vermont charm!"

Reviewed on Jul 6, 2024

Get rates
Waybury Inn
See all 877 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.

Frequently asked questions

How much does a Middlebury vacation package cost?
Offering excellent value package deals from ￥202,394 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 book a cheap Middlebury vacation package, consider traveling in January, March and November. You’ll typically find better rates on airfares and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for Middlebury?
When planning your Middlebury vacation, a handful of days will be enough to tour the best spots. Be sure to check out Town Hall Theater — it’s one of the top attractions in this destination. If you want more adventure, think about basing yourself here and going on some tours from Middlebury.
Is it worth booking a vacation package to Middlebury?
It’s easy to see why a Middlebury vacation is on the to-do list of many travelers. Popular attractions like Henry Sheldon Museum of Vermont History are just the start of what you can explore here.
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.
How to plan a trip to Middlebury?

  1. Choose when to go: Check your diary and get your bags packed. Your preferred season and the activities on offer will also help you decide when to escape to Middlebury.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and meals to activities and airfares. Your hotel will likely be the largest expense during your trip to Middlebury.
  3. Work out your trip length: Consider how long you want to spend exploring Middlebury. Plan your days so you can get to all the attractions and experiences you’re interested in at a leisurely pace.
  4. Bundle your airfare and accommodations: Once you’ve settled on your trip dates and duration, book the ideal Middlebury vacation package for you.

Discover the most popular places to visit in Middlebury

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