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Middlebury holiday rentals

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Best Middlebury holiday rentals

Most recommended holiday rentals in Middlebury

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Beautiful 4-Bedroom Home beside Middlebury College - Middlebury - Living room
Beautiful 4-Bedroom Home beside Middlebury College
Middlebury, VT, United States
Free Wi-Fi
Air conditioning
£557+
Check availability
Experience Vermont charm! Up to five bedrooms available Please inquire for rates - Middlebury - Living room
Experience Vermont charm! Up to five bedrooms available Please inquire for rates
Middlebury, VT, United States
Free Wi-Fi
Air conditioning
£697+
Check availability
MARCH '25 Huge Discount - Best Snow in 30 years! Up to 150/night off! - Middlebury - Living room
MARCH '25 Huge Discount - Best Snow in 30 years! Up to 150/night off!
Middlebury, VT, United States
Free Wi-Fi
Pet-friendly
Air conditioning
£513+
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, United States
10Wonderful(28)
Free Wi-Fi
Air conditioning
£468+
Check availability
Sun-filled, quiet country home on 27 acres with mountain views - Middlebury - Living room
Sun-filled, quiet country home on 27 acres with mountain views
Middlebury, VT, United States
Free Wi-Fi
Pet-friendly
Air conditioning
£529+
Check availability
Large And Luxurious Farmhouse - Close To Town And College! - Middlebury - Building
Large And Luxurious Farmhouse - Close To Town And College!
Middlebury, VT, United States
Air conditioning
£1,389+
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Mountain-view House ~ Mins To Middlebury, Flex Cancellation Policy - Middlebury - Outdoor view
Mountain-view House ~ Mins To Middlebury, Flex Cancellation Policy
Middlebury, VT, United States
Free Wi-Fi
Air conditioning
£375+
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In the heart of town, a modern farmhouse - Middlebury - Kitchen
In the heart of town, a modern farmhouse
Middlebury, VT, United States
Free Wi-Fi
Pet-friendly
Air conditioning
£520+
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Cozy Private Bedroom with Own Entrance - No Shower - Middlebury - Bedroom
Cozy Private Bedroom with Own Entrance - No Shower
Middlebury, VT, United States
Air conditioning
£91+
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Great Location! Cozy Two Bedroom Apartment in the Heart of Middlebury - Middlebury - Living room
Great Location! Cozy Two Bedroom Apartment in the Heart of Middlebury
Middlebury, VT, United States
Free Wi-Fi
Air conditioning
£710+
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Middlebury Home with Sunset views! - Middlebury
Middlebury Home with Sunset views!
Middlebury, VT, United States
Pet-friendly
Air conditioning
£254+
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An Idyllic Vermont Experience Minutes from Middlebury College! - Middlebury
An Idyllic Vermont Experience Minutes from Middlebury College!
Middlebury, VT, United States
Air conditioning
£301+
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Downtown Middlebury 3 Br Home - Walk Everywhere! - Middlebury
Downtown Middlebury 3 Br Home - Walk Everywhere!
Middlebury, VT, United States
Pet-friendly
Air conditioning
£197+
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Charming Cottage within walking distance of Middlebury College/canoe available - Middlebury
Charming Cottage within walking distance of Middlebury College/canoe available
Middlebury, VT, United States
Air conditioning
£244+
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Beautiful views, quiet dirt road, plenty of VT charm! - Middlebury
Beautiful views, quiet dirt road, plenty of VT charm!
Middlebury, VT, United States
Free Wi-Fi
Air conditioning
£281+
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Downtown Middlebury River House - Middlebury
Downtown Middlebury River House
Middlebury, VT, United States
9.7Wonderful(35)
Parking
Free Wi-Fi
Air conditioning
£361+
Check availability
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KAYAK's top tips for finding Middlebury holiday rental deals

  • Holiday rentals in Middlebury are around 70% more expensive than hotels on average. Search here to compare prices for all accommodation types in Middlebury.
  • The best holiday rental properties in Middlebury are Middlebury Gem open concept and 5 minutes from town (10.0, 28 reviews), Downtown Middlebury River House (9.7, 35), and Beautiful 4-Bedroom Home beside Middlebury College (9.4, 30), based on ratings and reviews from real travellers.

FAQs when booking a holiday home in Middlebury

  • What types of holiday rentals are available in Middlebury?

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

  • Are there any pet-friendly holiday rentals in Middlebury?

    There are a number of dog and pet-friendly Middlebury holiday rentals, with around 21% allowing you to bring your pet along with you.

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

    Take a look at our holiday rentals map to find the best holiday 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 holiday rental.

Everything you need to know for your stay in Middlebury

Middlebury holiday rental deals. Search for holiday homes, apartments, condos, cabins, cottages, villas and more in Middlebury. Find cheap holiday homes to rent in Middlebury. KAYAK searches hundreds of travel sites to help you find and book a holiday rental in Middlebury that suits you best.

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