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.
Ready to book your vacation to Middlebury?
Middlebury Hotel Deals
Middlebury Inn
14 Court Square Middlebury VT
Fully refundableReserve now, pay when you stay
CA $186
CA $205 total
Nov 1 - Nov 2
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"The property is Victorian chic. The stay at Middlebury was a delightful vintage experience. The room features modern furniture for comfortable sleep. The hotel is within walking distance of Main St shops and Middlebury College."
Reviewed on Oct 7, 2026
Courtyard Middlebury
309 Court Street Middlebury VT
Fully refundableReserve now, pay when you stay
CA $180
CA $198 total
Nov 1 - Nov 2
includes taxes & fees
Swift House Inn
57 North Pleasant Street Middlebury VT
CA $293
CA $322 total
Nov 3 - Nov 4
includes taxes & fees
9.6/10 Exceptional! (367 reviews)
"Always enjoy staying at the Swift House Inn. The rooms are all well appointed and the incredible breakfast at Jessica’s is such a lovely bonus. You won’t be disappointed when choosing the Swift House in Middlebury… beats every other accommodation by a mile!"
Reviewed on Oct 4, 2026
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.
Stay near popular Middlebury attractions
Middlebury College
9.6/10 (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.
UVM Morgan Horse Farm
9.4/10 (13 reviews)
You can take time to visit UVM Morgan Horse Farm during your travels to Weybridge. While you're here, you can savor the top-notch restaurants.
Town Hall Theater
9.0/10 (8 reviews)
Enjoy a performance at Town Hall Theater, a storied theater in Middlebury. Stroll along the riverfront or discover the area's waterfalls.
Henry Sheldon Museum of Vermont History
8.0/10 (1 review)
You can study the exhibits at Henry Sheldon Museum of Vermont History, a museum with a story of its own, during your travels to Middlebury. Stroll along the riverfront or discover the area's waterfalls.
Vermont Folklife Center
9.6/10 (4 reviews)
Enjoy an outing to Vermont Folklife Center during your stay in Middlebury. While you're here, you can savor the top-notch restaurants.
Cornwall Swamp Wildlife Management Area
Explore the great outdoors at Cornwall Swamp Wildlife Management Area, a lovely green space in Cornwall.
Kevin P. Mahaney '84 Center for the Arts
10.0/10 (10 reviews)
Enjoy a performance at Kevin P. Mahaney '84 Center for the Arts, a theater with a story to tell in Middlebury. While you're here, you can savor the top-notch restaurants.
Middlebury Falls
Commune with nature and explore the great outdoors at Middlebury Falls during your travels in Middlebury. You can enjoy the restaurants while in the area.
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?
- 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.
- 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.
- 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.
- Bundle your accommodations and airfare: After you've nailed down 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.
