Middlebury Rentals
From $166 per night (USD)VRBO
Charming, spacious home near towncenter amenities, resturants, trails and parks.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Charming, spacious, and inviting, Spruce House is a cozy, updated circa 1900s 1 ½ story home conveniently located just s ...
From $166 per night (USD)VRBO
From $231 per night (USD)Expedia
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
HOT TUB! There's a brand-new hot tub on this property that is ready for unlimited fun! This fully renovated 3 bed/2 bath ...
From $231 per night (USD)Expedia
From $457 per night (USD)VRBO
The Loft 3BR Apartment with Scenic Deck
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to our lofty, bright and cozy 3-bedroom apartment, perched over the heart of downtown Middlebury. With its invi ...
From $457 per night (USD)VRBO
From $296 per night (USD)Expedia
Charming 3-bedroom house located on Main Street in Downtown Middlebury
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Nestled in the heart of charming Middlebury, The Cozy Cottage on Main Street is the perfect family-friendly retreat for ...
From $296 per night (USD)Expedia
From $353 per night (USD)VRBO
Charming 1912 Bungalow in Middlebury Indiana
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Filled with character, charm and history. Once the home of the Kenneth Krider family. He played an integral role in Kr ...
From $353 per night (USD)VRBO
From $209 per night (USD)Expedia
| Hot Tub | Amish Farm Country | Pergola | Deck |
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Backyard country living at its absolute finest!! Hot tub, back deck, patio, pergola, grill, pastureland, fire pit, open ...
From $209 per night (USD)Expedia
From $144 per night (USD)VRBO
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You are encouraged to get trip insurance. We follow our cancellation policy. Welcome to the Red Thread Retreat! We are ...
From $144 per night (USD)VRBO
From $474 per night (USD)VRBO
Charming Middlebury Retreat w/ Patio & Fire Pit
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to this cozy 3-bedroom, 3-bath vacation rental in Middlebury! The inviting home boasts a furnished patio for sip ...
From $474 per night (USD)VRBO
From $157 per night (USD)VRBO
Solar powered-Charming 1-Bedroom in Middlebury
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This adorable warm place in Middlebury is the perfect spot for your unplugged escape. With a cozy bedroom and a charming ...
From $157 per night (USD)VRBO
From $194 per night (USD)Expedia
Freedom Farm
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
About this space Welcome to Amish Country. Enjoy the picturesque countryside in the comfort of a converted Amish home an ...
From $194 per night (USD)Expedia