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.
Smart Suites on the Hill

Smart Suites on the Hill

2.5 out of 5
per person
Oct 6 - Oct 9
found 11 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Burlington (BTV)
6.8/10 (57 reviews)
Before booking this trip, I noticed a lot of reviews that mentioned lack of cleanliness, or coming off as old-fashioned. I don’t think either are true. Only issue was construction cutting off the shortest route to the building, but I had a great time. Thanks guys! :)

Reviewed on Jul. 19, 2025

Outbound Stowe

Outbound Stowe

3.5 out of 5
per person
Oct 6 - Oct 9
found 11 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Burlington (BTV)
9/10 Wonderful! (169 reviews)
Super nice property at on the Stowe path.

Reviewed on Aug. 4, 2025

Smugglers' Notch Resort Private Suites

Smugglers' Notch Resort Private Suites

3.5 out of 5
per person
Oct 6 - Oct 9
found 11 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Burlington (BTV)
7.8/10 Good! (17 reviews)
Club Wyndham Smugglers’ Notch Vermont

Club Wyndham Smugglers’ Notch Vermont

3.5 out of 5
per person
Oct 6 - Oct 9
found 11 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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

Basin Harbor

Basin Harbor

3.5 out of 5
per person
Oct 6 - Oct 9
found 11 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Burlington (BTV)
8.4/10 Very Good! (178 reviews)
My husband and I stayed at this property because we are driving from the New England coast to upstate New York and wanted a halfway place in the extreme heat. I had remembered this place finally from a couple visits when I was a little girl and had always wanted to go back. We had a lovely room and one of the cottages we had great meals at the main restaurant and the Red Mill. We loved swimming in the lake at the resort and at Button Bay Park. My husband visited the nearby Marine museum, and I had a wonderful visit at the Shelburne Museum. The staff were professional and extra courteous! Only two things that I would change: The breakfast options were extremely limited. Large Buffet in main dining room, or coffee and small choice of pastries at the main lodge store. Sub par coffee machines in the room. I recommend adding a place to get good coffee and a small continental breakfast on site. The other issue that we had is the trail to Button Bay park was not well marked, the signage needs to be enhanced. We got slightly lost, but met a couple the next day who got really lost for the same reason. I went to Vergennes, 15 minutes away to find good coffee and there are some nice small shops there.

Reviewed on Jul. 29, 2025

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Middlebury Hotel Deals

Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square, Middlebury, VT
The price is CA $185 per night from Aug 13 to Aug 14
CA $185
CA $203 total
Aug 13 - Aug 14
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 6 to Aug 7
CA $212
CA $233 total
Aug 6 - Aug 7
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.
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Frequently asked questions

How much does a Middlebury vacation package cost?
You'll find cheap prices from CA $1,182 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.