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Holiday rentals in Middlebury

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Popular amenities for Middlebury holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Homes with more space

Top guest favourite
Vibrant orange tulips bloom in the foreground, contrasting with lush green foliage. A sign for Studio Holtquist is visible in the background, alongside colorful artistic sculptures standing amidst a bed of pink flowers. The scene is set against a backdrop of trees, indicative of a serene environment.
Home in Woodbury
4.99 out of 5 average rating, 138 reviews

Your Perfectly Wonderful Woodbury Sanctuary!

Top guest favourite
A view of a classic farmhouse, surrounded by green grass and trees. Hay is scattered across the foreground, and the house features a porch with visible outdoor seating. A quiet road is seen in the distance, offering a glimpse of the serene rural setting.
Home in Bethlehem
4.97 out of 5 average rating, 314 reviews

Litchfield County Farmhouse with a Modern Twist

Superhost
A well-equipped kitchen features wooden shelves with dishes and a coffee maker. A modern sink and black faucet are complemented by a smooth countertop, while natural light filters through a window adorned with greenery. Kitchen essentials are organized for convenience.
Flat in Brookfield
4.91 out of 5 average rating, 303 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Guest favourite
A view from a balcony showcases a setting sun over a tranquil landscape. The scene includes treetops and distant structures, while soft sunlight casts warm hues across the space. A wooden railing frames the balcony, providing a clear perspective of the serene outdoor environment.
Flat in Waterbury
4.97 out of 5 average rating, 32 reviews

Cozy 1b/1b beautiful views Hopeville Wtby 2nd Flr

Destinations to explore