
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
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



von Trapp Family Lodge & Resort
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
Middlebury Hotel Deals

Middlebury Inn
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

Courtyard Middlebury
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

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