Middlebury Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

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

Top Middlebury Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Club Wyndham Smugglers’ Notch Vermont

Club Wyndham Smugglers’ Notch Vermont

3.5 out of 5
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
8.4/10 Very Good! (175 reviews)
Lovely large room. Loved having the washer dryer in the room. Pool is close to the room. Nice and quiet.

Reviewed on Jul. 14, 2025

Outbound Stowe

Outbound Stowe

3.5 out of 5
Save 100% on your flight
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
9/10 Wonderful! (149 reviews)
An ideal resort hotel staffed by great people.

Reviewed on Jul. 13, 2025

Smugglers' Notch Resort Private Suites

Smugglers' Notch Resort Private Suites

3.5 out of 5
Save 100% on your flight
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
7.8/10 Good! (17 reviews)
AWOL Stowe

AWOL Stowe

3.5 out of 5
per person
Oct 6 - Oct 11
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
9/10 Wonderful! (152 reviews)
Beautiful property with hot tub, sauna and cold plunge. Adults only.

Reviewed on Jul. 13, 2025

Sonesta ES Suites Burlington VT

Sonesta ES Suites Burlington VT

3 out of 5
Williston South
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
7/10 Good! (1,004 reviews)
Tub did not drain well. Otherwise everything else was great

Reviewed on Jul. 14, 2025

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
The price is CA $221 per night from Jul 22 to Jul 23
CA $221
CA $243 total
Jul 22 - Jul 23
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"The property itself was unique!! Really cool and the food was delicious! Front desk staff was excellent but one in the restaurant left something to be desired. I will definitely be staying there again."

Reviewed on Jul. 14, 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 $196 per night from Jul 27 to Jul 28
CA $196
CA $216 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (518 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
Swift House Inn

Swift House Inn

3 out of 5
57 North Pleasant Street, Middlebury, VT
The price is CA $245 per night from Jul 20 to Jul 21
CA $245
CA $270 total
Jul 20 - Jul 21
includes taxes & fees
9.4/10 Exceptional! (278 reviews)
"What a wonderful Inn. Great staff. Great room. Great food. What more could you ask for!"

Reviewed on Jul. 13, 2025

Swift House Inn
See all 923 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 $1,470 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.