Middlebury Vacation Packages

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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.

Top Middlebury Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Whitney's Inn at Jackson

The Whitney's Inn at Jackson

3 out of 5
per person
Apr. 18 - Apr. 21
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
8.2/10 Very Good! (471 reviews)
My girlfriend and I stayed at Whitney’s inn for a Valentine’s Day / Presidents’ Day weekend getaway and it was so perfect! We skied at Black mountain two days and it was so easy to get to and from the inn to the slopes. The inn itself was really quaint and cute. There’s also the shovel handle pub right nearby which was a great vibe. Whitney’s inn also offers services and amenities at the Christmas farm inn which we didn’t use but was still nice to have! We will definetly be coming back and loved our stay!

Reviewed on Feb. 19, 2025

Kearsarge Inn

Kearsarge Inn

2.5 out of 5
North Conway Village
per person
Apr. 18 - Apr. 21
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
9.6/10 Exceptional! (1,004 reviews)
Awesome people. Awesome place.

Reviewed on Feb. 28, 2025

Top Notch Inn

Top Notch Inn

3 out of 5
per person
Apr. 18 - Apr. 21
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
9.4/10 Exceptional! (1,006 reviews)
Skiing at Wildcat? Definitely consider Top Notch. Close to the Mountain and on the Main Street with plenty of options for food, coffee, and laundry.

Reviewed on Feb. 26, 2025

Quality Inn & Suites

Quality Inn & Suites

2.5 out of 5
per person
Apr. 18 - Apr. 21
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
7.6/10 Good! (554 reviews)
Everything was as expected except breakfast. Well below average. Fruits were not there except for an apple, 1 apple. Milk was not provided.

Reviewed on Jan. 20, 2025

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Middlebury Hotel Deals

Middlebury Inn
Middlebury Inn
3 out of 5
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Mar. 4 to Mar. 5
CA $192
CA $211 total
includes taxes & fees
Mar 4 - Mar 5
8.8/10 Excellent! (1,001 reviews)
"We loved the character of the property, its history and charm. The staff were very friendly and our dining experience was very good."

Reviewed on Feb. 25, 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 CA $205 per night from Mar. 27 to Mar. 28
CA $205
CA $226 total
includes taxes & fees
Mar 27 - Mar 28
8.8/10 Excellent! (498 reviews)
"Perfect"

Reviewed on Feb. 19, 2025

Courtyard Middlebury
Swift House Inn
Swift House Inn
3 out of 5
57 North Pleasant Street, Middlebury, VT
The price is CA $287 per night from Mar. 2 to Mar. 3
CA $287
CA $316 total
includes taxes & fees
Mar 2 - Mar 3
9.4/10 Exceptional! (263 reviews)
"Great"

Reviewed on Feb. 16, 2025

Swift House Inn
See all 878 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

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Family Vacations

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Frequently asked questions

How much does a Middlebury vacation package cost?
Offering excellent value package deals from CA $536 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.

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