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.
Outbound Stowe

Outbound Stowe

3.5 out of 5
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
9/10 Wonderful! (169 reviews)
Super nice property at on the Stowe path.

Reviewed on Aug. 4, 2025

Club Wyndham Smugglers’ Notch Vermont

Club Wyndham Smugglers’ Notch Vermont

3.5 out of 5
per person
Oct 17 - Oct 22
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
8.4/10 Very Good! (183 reviews)
Beautiful, clean and well maintained property. Beautiful view from the deck. Property includes everything you need!

Reviewed on Aug. 5, 2025

Swanson Inn of Vermont

Swanson Inn of Vermont

3 out of 5
per person
Oct 17 - Oct 22
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
9.6/10 Exceptional! (154 reviews)
A mixed bag. Nice views of brook, woods & mountain. Frank was very helpful! The room was comfortable but the door was broken. No pancakes or waffles; just a lousy continental breakfast & bad coffee.

Reviewed on Jul. 21, 2025

Bluebird Cady Hill Lodge

Bluebird Cady Hill Lodge

3 out of 5
per person
Oct 17 - Oct 22
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
9.2/10 Wonderful! (526 reviews)
Very nice property. Room was neat and clean but the AC unit was very loud.

Reviewed on Jul. 31, 2025

Comfort Inn & Suites Montpelier-Berlin

Comfort Inn & Suites Montpelier-Berlin

2.5 out of 5
per person
Oct 17 - Oct 22
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
9.6/10 Exceptional! (1,002 reviews)
lovely hotel for a quick night in Montpellier.

Reviewed on Aug. 4, 2025

Ready to book your vacation to Middlebury?

 

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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 $196 per night from Aug 17 to Aug 18
CA $196
CA $216 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"was quite a unique & comforting hotel!"

Reviewed on Aug. 3, 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 $197 per night from Aug 17 to Aug 18
CA $197
CA $217 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (519 reviews)
"Everything was good, except that we asked for full housekeeping and they did not change the linens."

Reviewed on Jul. 5, 2025

Courtyard Middlebury
Middlebury Sweets Motel

Middlebury Sweets Motel

2.5 out of 5
1395 Rt 7 South, Middlebury, VT
The price is CA $212 per night from Aug 7 to Aug 8
CA $212
CA $233 total
Aug 7 - Aug 8
includes taxes & fees
8.4/10 Very Good! (367 reviews)
"Nice and clean. Plus we love the candy shop!"

Reviewed on Aug. 4, 2025

Middlebury Sweets Motel
See all 922 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

Frequently asked questions

How much does a Middlebury vacation package cost?
You'll find cheap prices from CA $1,101 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.

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