Middlebury vacation rentals

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Recommended by KAYAK

Best Middlebury vacation rentals

Experience Vermont charm! Up to 5 bedrooms available Please inquire for rates - Middlebury - Building
Experience Vermont charm! Up to 5 bedrooms available Please inquire for rates
Middlebury, VT
10Wonderful(13)
House
Free Wi-Fi
$1,317+
Check availability
Middlebury Gem open concept and 5 minutes from town - Middlebury - Dining room
Middlebury Gem open concept and 5 minutes from town
Middlebury, VT
10Wonderful(36)
House
Free Wi-Fi
$580+
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Large And Luxurious Farmhouse - Close To Town And College! - Middlebury - Building
Large And Luxurious Farmhouse - Close To Town And College!
Middlebury, VT
9.8Wonderful(19)
House
$1,631+
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Downtown Middlebury Waterfall Studio Apartment - Middlebury - Kitchen
Downtown Middlebury Waterfall Studio Apartment
Middlebury, VT
10Wonderful(2)
Apartment
$186+
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Custom Home just minutes from Middlebury - Middlebury - Living room
Custom Home just minutes from Middlebury
Middlebury, VT
10Wonderful(22)
House
Free Wi-Fi
$499+
Check availability
Beautiful 4-Bedroom Home beside Middlebury College - Middlebury - Living room
Beautiful 4-Bedroom Home beside Middlebury College
Middlebury, VT
9.5Wonderful(53)
House
Free Wi-Fi
$605+
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Downtown Middlebury River House - Middlebury - Living room
Downtown Middlebury River House
Middlebury, VT
9.7Wonderful(39)
House
Parking
Free Wi-Fi
$1,102+
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In the heart of town, a modern farmhouse - Middlebury - Kitchen
In the heart of town, a modern farmhouse
Middlebury, VT
10Wonderful(21)
House
Free Wi-Fi
$729+
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Newly Renovated 3-bedroom house within walking distance to downtown Middlebury - Middlebury - Living room
Newly Renovated 3-bedroom house within walking distance to downtown Middlebury
Middlebury, VT
10Wonderful(2)
House
Free Wi-Fi
$516+
Check availability
Mountain-view House ~ Mins To Middlebury, Flex Cancellation Policy - Middlebury - Bedroom
Mountain-view House ~ Mins To Middlebury, Flex Cancellation Policy
Middlebury, VT
9.9Wonderful(20)
House
Free Wi-Fi
$499+
Check availability
Chic Downtown Cottage Uber Walkable Hot Tub Pet Friendly - Middlebury - Living room
Chic Downtown Cottage Uber Walkable Hot Tub Pet Friendly
Middlebury, VT
10Wonderful(5)
House
Free Wi-Fi
$831+
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Yurt in Middlebury, Vermont - Middlebury
Yurt in Middlebury, Vermont
Middlebury, VT
10Wonderful(3)
Apartment
$109+
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

November
September
$504
$593
Cheapest month to stay with an average 65% drop in price.
Most expensive month to stay with an average 47% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Middlebury vacation rental deals

  • The best vacation rental properties in Middlebury are Custom Home just minutes from Middlebury (10.0, 22 reviews), In the heart of town, a modern farmhouse (10.0, 21), and Middlebury Gem open concept and 5 minutes from town (10.0, 36), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Middlebury, you should consider visiting during the low season. The cheapest vacation homes in Middlebury can be found in November and July.
  • The cheapest night for renting a vacation home in Middlebury is Tuesday. In contrast, the most expensive is Wednesday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Middlebury for 5 days.

FAQs when booking a vacation home in Middlebury

  • What types of vacation rentals are available in Middlebury?

    There are loads of different property types that you can make your vacation home in Middlebury. You’ll find apartments, cabins and houses.

  • How can I find vacation rentals near me in Middlebury?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Middlebury?

Our map will help you find the perfect place to stay in Middlebury by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Middlebury