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.
Cranmore Mountain Lodge Bed & Breakfast

Cranmore Mountain Lodge Bed & Breakfast

3 out of 5
Kearsarge
Price was CA $1,009, price is now CA $883 per person
CA $883
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Burlington (BTV)
8.8/10 Excellent! (237 reviews)
We stayed in the detached loft building. It was clean and just what we needed. Our two double bed room was pretty small. Bathroom was also small. about the only complaint was with the hvac setup. It wasn’t really all that clear which baseboard electric units for heat were supposed to actually work. There’s a thermostat on the wall, but only the one by the door was functional; two were cold. There’s also a window unit, but I’m guessing that was for summer air conditioning. Some in-room literature would have been helpful. I think I’d prefer to stay in the main lodge next time. Also, we were woken in the middle of the night up by a fire alarm. Getting dressed and going outside in a snowstorm at 2-3am isn’t great. Apparently it was only in the loft building. It was a false alarm, but in a building like that, better safe than sorry. Breakfast food and service was great. I’ve stayed in a ton of places around North Conway over the years and they all seem somewhat old and dated, so I get it, and I wasn’t disappointed. It was clean, a priority, and the beds were comfortable.

Reviewed on Mar. 5, 2025

Club Wyndham Smugglers’ Notch Vermont

Club Wyndham Smugglers’ Notch Vermont

3.5 out of 5
Price was CA $1,386, price is now CA $1,190 per person
CA $1,190
per person
Sep 24 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
8.4/10 Very Good! (190 reviews)
Great room. Nice walking trails.

Reviewed on Aug. 21, 2025

Outbound Stowe

Outbound Stowe

3.5 out of 5
Price was CA $1,313, price is now CA $1,136 per person
CA $1,136
per person
Sep 24 - Sep 26
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
9/10 Wonderful! (187 reviews)
Loved our stay so much we stayed an extra day.

Reviewed on Aug. 15, 2025

von Trapp Family Lodge & Resort

von Trapp Family Lodge & Resort

3.5 out of 5
Price was CA $1,680, price is now CA $1,491 per person
CA $1,491
per person
Sep 24 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
9/10 Wonderful! (867 reviews)
MAGICAL PLACE, VIEWS ARE SPECTACULAR, DINING CHOICES FANTASTIC. LOVE THE HISTORY OF THIS PROPERTY

Reviewed on Aug. 17, 2025

Basin Harbor

Basin Harbor

3.5 out of 5
Price was CA $1,237, price is now CA $1,099 per person
CA $1,099
per person
Sep 24 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Burlington (BTV)
8.4/10 Very Good! (181 reviews)
Basin harbor is The best!!

Reviewed on Aug. 18, 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
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Sep 16 to Sep 17
CA $207
CA $228 total
Sep 16 - Sep 17
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"The room smelled. I think the carpet needs to be replaced."

Reviewed on Aug. 20, 2025

Middlebury Inn
Courtyard Middlebury

Courtyard Middlebury

3 out of 5
309 Court Street, US Rt 7 / Historic Ethan Allen Hwy, Middlebury, VT
The price is CA $199 per night from Sep 7 to Sep 8
CA $199
CA $219 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (522 reviews)
"Daily or at least every other day housekeeping service would have been appreciated."

Reviewed on Aug. 14, 2025

Courtyard Middlebury
Brandon Inn

Brandon Inn

3 out of 5
20 Park Street, Brandon, VT
The price is CA $201 per night from Aug 24 to Aug 25
CA $201
CA $222 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (505 reviews)
"Great stay"

Reviewed on Aug. 20, 2025

Brandon Inn
See all 917 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 $883 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.