Middlebury Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.

Ready to book your vacation to Middlebury?

 

Choose your dates

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 $156 per night from Jul 8 to Jul 9
CA $156
CA $172 total
Jul 8 - Jul 9
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Power went out for 3hrs 7am-10am. Asked at front desk about partial compensation, desk person said management was going to send email, but haven't heard back"

Reviewed on Jun 29, 2026

Middlebury Inn
Courtyard Middlebury

Courtyard Middlebury

3 out of 5
309 Court Street Middlebury VT
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Jul 5 to Jul 6
CA $212
CA $233 total
Jul 5 - Jul 6
includes taxes & fees
8.8/10 Excellent! (575 reviews)
"Room was clean but all rooms need a refresh. We stay at this location a few times a year. Lobby is laid out so well. Great location."

Reviewed on Jun 30, 2026

Courtyard Middlebury
Swift House Inn

Swift House Inn

3 out of 5
57 North Pleasant Street Middlebury VT
The price is CA $318 per night from Jul 5 to Jul 6
CA $318
CA $350 total
Jul 5 - Jul 6
includes taxes & fees
9.6/10 Exceptional! (343 reviews)
"Great room!"

Reviewed on Jun 28, 2026

Swift House Inn
See all 979 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
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Middlebury attractions

Middlebury College

9.6/5 (285 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.
See properties

Frequently asked questions

How much does a Middlebury vacation package cost?
You'll find cheap prices on Expedia for your Middlebury escape. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Middlebury costs.
What are the cheapest months to go to Middlebury?
You're likely to find lower prices and better availability in January, March and November. Take a look at our cheap Middlebury vacation packages and you could land some great off-season discounts.
How many days is enough for Middlebury?
Usually, a handful of days is great for a Middlebury vacation. With a well-organized itinerary, you can see all the main sights including Town Hall Theatre, as well as explore some hidden treasures along the way.
Is it worth booking a vacation package to Middlebury?
It's no wonder a Middlebury vacation is on the to-do list of many travellers. Well-known attractions like Henry Sheldon Museum of Vermont History are just the beginning of what you can explore here.
How to find the best Middlebury package deals?
Start your search for a Middlebury package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Middlebury package deal straight away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Middlebury adventure underway.
Is it cheaper to book a Middlebury vacation as a package?
You can enjoy significant savings on your Middlebury getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to view some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Middlebury?
Score fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Middlebury break.
How to plan a trip to Middlebury?

  1. Choose when to travel: Check your diary and get your bags packed. Your preferred season and the available activities will also help you decide when to escape to Middlebury.
  2. Plan your budget wisely: In addition to the cost of your hotel, you should consider other expenses too. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that could crop up during your trip to Middlebury.
  3. Decide how long to go for: Now that you're up to speed on Middlebury, you can work out the right length of your vacation. Pull together a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your accommodations and airfare: After you've nailed down your trip dates and duration, book the ideal Middlebury vacation package for you.

Explore a world of travel with Expedia

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