Middlebury, Vermont

Vacation Rentals in Middlebury, Vermont

Discover 12 vacation rental properties in Middlebury. From 1 to 4 bedrooms. Average $479/night. 100% have pools.

12 verified listings Book securely on VRBO Prices updated March 2026

12 properties available

Cozy Private Bedroom with Own Entrance - No Shower

Cozy Private Bedroom with Own Entrance - No Shower

1 bed 1 bath
PoolA/CWiFiBalcony
$72/night
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Downtown Middlebury 3 BR Home - Walk Everywhere!

Downtown Middlebury 3 BR Home - Walk Everywhere!

3 beds 1 bath
PoolA/CWiFiBalcony
$213/night
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Great Location! Cozy Two Bedroom Apartment in the Heart of Middlebury

Great Location! Cozy Two Bedroom Apartment in the Heart of Middlebury

2 beds 1 bath
PoolA/CWiFiBalcony
$632/night
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*Downtown Middlebury Waterfall Studio Apartment*

*Downtown Middlebury Waterfall Studio Apartment*

1 bed 1 bath
PoolA/CWiFiBalcony
$192/night
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In the heart of town, a modern farmhouse

In the heart of town, a modern farmhouse

3 beds 1 bath
PoolA/CWiFiBalcony
$517/night
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Beautiful 4-Bedroom Home beside Middlebury College

Beautiful 4-Bedroom Home beside Middlebury College

4 beds 2 baths
PoolA/CWiFiBalcony
$427/night
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Middlebury, VT Newly renovated four bedroom Luxury Home (sleeps 8)

Middlebury, VT Newly renovated four bedroom Luxury Home (sleeps 8)

3 beds 1 bath
PoolA/CWiFiBalcony
$1,455/night
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Middlebury Gem open concept and 5 minutes from town

Middlebury Gem open concept and 5 minutes from town

3 beds 2 baths
PoolA/CWiFiBalcony
$396/night
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River House in the Heart of Middlebury

River House in the Heart of Middlebury

3 beds 2 baths
PoolA/CWiFiBalcony
$646/night
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Newly Renovated 3-bedroom house within walking distance to downtown Middlebury

Newly Renovated 3-bedroom house within walking distance to downtown Middlebury

3 beds 1 bath
PoolA/CWiFiBalcony
$395/night
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Middlebury Home with Sunset views!

Middlebury Home with Sunset views!

2 beds 2 baths
PoolA/CWiFiBalcony
$202/night
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CHIC DOWNTOWN COTTAGE ★UBER WALKABLE ★HOT TUB ★PET FRIENDLY

CHIC DOWNTOWN COTTAGE ★UBER WALKABLE ★HOT TUB ★PET FRIENDLY

4 beds 2 baths
PoolA/CWiFiBalcony
$596/night
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