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Latest Vacation Rentals in Middlebury VT (23)

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4 Br Private Vacation Home Vacation Rental In Cornwall, Vermont

This newly renovated one-story home is 2.1 miles from Middlebury College. Three bedrooms, three full baths (one with a deep soaking tub), and a study which sleeps 2! The living room and kitchen...

Created Jun 16, 2024

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2 Br Apartment Vacation Rental In Middlebury, Vermont

Boho Chic and freshly redecorated apartment in the heart of Middlebury. Walking distance to campus, the athletic fields, downtown and 5 minutes drive from Porter Hospital. Beautiful shared backyard...

Created Jun 16, 2024

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5 Br Private Vacation Home Vacation Rental In Cornwall, Vermont

Please inquire for datesUpdate 4/2024 : Property is currently being renovated to add a two story great room that includes additional fireplace, a new king BR with ensuite bathroom, a new queen...

Created Jun 16, 2024

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4 Br Private Vacation Home Vacation Rental In Cornwall, Vermont

Custom home built by the owner in 2004. Country setting in an orchard with Middlebury College just a five minute drive away. This is a quiet neighborhood surrounded by rural properties, operating...

Created Jun 16, 2024

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2 Br Apartment Vacation Rental In Middlebury, Vermont

This early-1900s Middlebury home has long been split as a duplex with an upper / lower apartment. We've made recent updates, decorated, and furnished the first floor unit for short term use and we...

Created Jun 16, 2024

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3 Br Private Vacation Home Vacation Rental In Middlebury, Vermont

Convenient in-town living and the solitude of a private retreat on the banks of the Otter Creek River. This sophisticated home has two floors of at grade living space, builder/designer renovated,...

Created Jun 16, 2024

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4 Br Private Vacation Home Vacation Rental In Middlebury, Vermont

This property is a beautiful four-bedroom home located in a small, private neighborhood. The backyard of the house borders Middlebury College campus and is a short walk to the athletic fields and...

Created Jun 16, 2024

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5 Br Private Vacation Home Vacation Rental In Cornwall, Vermont

This incredible home in picturesque Cornwall, Vermont is the perfect place to stay - just 10 minutes from Middlebury and with everything you need. A gorgeous retreat on 18 acres, this spacious home...

Created Jun 16, 2024

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3 Br Private Vacation Home Vacation Rental In Middlebury, Vermont

This home is in the heart of the town of Middlebury and within walking distance to college, downtown and grocery stores. It is perfect for just two people or a large group or family. Completely...

Created Jun 16, 2024

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2 Br Private Vacation Home Vacation Rental In Cornwall, Vermont

Updated and elegantly comfortable house with open floor plan; 2 bedrooms, 2 bathrooms (with addition pull-out couch downstairs for overflow)--overlooking gardens and the Adirondack mountains and...

Created Jun 16, 2024

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3 Br Apartment Vacation Rental In Middlebury, Vermont

This 1918 downtown Middlebury home has long been split into a left and right duplex. We have decorated and furnished unit #2 for short term rental use and we know that you will have a positive...

Created Jun 16, 2024

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3 Br Private Vacation Home Vacation Rental In Middlebury, Vermont

This Middlebury house boasts 3 inviting bedrooms. With 2 queen beds and 1 full bed, it's the perfect retreat for guests seeking a comfortable and relaxing stay. The property offers all the...

Created Jun 16, 2024

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3 Br Private Vacation Home Vacation Rental In Middlebury, Vermont

Our in-town home is available for short term rentals during Middlebury College event weekends, as well as select weeks during the summer and academic year. Conveniently located within Middlebury...

Created Jun 16, 2024

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1 Br Apartment Vacation Rental In Cornwall, Vermont

Beautifully appointed, recently custom built very private one-bedroom apartment with gorgeous views of the Green mountains, lush fields and clay plain forests. In Spring, Summer and Fall sheep...

Created Jun 16, 2024

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4 Br Private Vacation Home Vacation Rental In Cornwall, Vermont

With its dramatic hilltop positioning, Pink House Farm offers breathtaking western Adirondack views. Sited on one of Addison County's most coveted roads, this luxurious 1798 farmhouse has been...

Created Jun 16, 2024

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2 Br Agritourism Vacation Rental In Cornwall, Vermont

Our guesthouse is nestled in the Lemon Faire River Valley. This 1 bedroom with kitchen, bathroom, and extra sleeping loft gives you a quiet experience of the Vermont countryside. The outside entry...

Created Jun 16, 2024

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1 Br Apartment Vacation Rental In Middlebury, Vermont

Downtown Middlebury furnished studio apartment with a picturesque view of Otter Creek waterfalls! This historic 1700s building has retail shops on the first floor and the apartment is...

Created Jun 16, 2024

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4 Br Private Vacation Home Vacation Rental In Middlebury, Vermont

The Middlebury Cottage is located on a teeny tiny street smack dab in the HEART OF MIDDLEBURY VILLAGE! In a 5-10 minute WALK you can be on the Middlebury College campus, Main Street OR on the...

Created Jun 16, 2024

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1 Br Private Vacation Home Vacation Rental In Middlebury, Vermont

This is a private one bedroom with half-bath (no shower) and your own entrance with a ramp. This space is attached to the main house but separated by a locked door for your privacy. Located in the...

Created Jun 16, 2024

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3 Br Private Vacation Home Vacation Rental In Weybridge, Vermont

Perfectly located on a dirt road, but only 3 miles from downtown Middlebury, VT, this house is the ideal landing spot for outside adventures with family and friends. It's easy to hop on the Trail...

Created Jun 16, 2024

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1br Cottage Vacation Rental In Cornwall, Vermont

Located just 7 miles outside of Middlebury, offering privacy and expansive views of the Green Mountains. Newly built and furnished with quality and luxury in mind. A queen bed is located in the bedr

Created Mar 22, 2022

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3br House Vacation Rental In Cornwall, Vermont

Fantastic 3000ft modern house with beautiful views and only 5 minutes from Middlebury College available for rent. Full house available for our guests with the host residing in a suite on the back of

Created Mar 22, 2022

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1br Guest House Vacation Rental In Middlebury, Vermont

Sweet & peaceful studio apartment in Middlebury This adorable guest apartment on Chipman Hill has all that you need for a short (or long!) stay in Middlebury. Recently constructed, it has many thoug

Created Mar 22, 2022

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