Discover a selection of 29 vacation rentals in Middlebury that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and air conditioning. Prices start at $120 per night, and houses and cabins are popular options for a stay in Middlebury. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Middlebury
Destination guide

Take in the natural beauty of Middlebury

The gardens and surrounding scenery provide a peaceful ambiance to your vacation home in Middlebury. Travelers to this welcoming city praise the shopping, hiking and biking. Many of our vacation rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.


Activities and attractions in and around Middlebury

Are you looking for top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Middlebury a one-of-a-kind vacation spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Shipshewana Auction and Flea Market (6.5 mi / 10.4 km)
  • Elkhart County Fairgrounds (8.4 mi / 13.5 km)
  • NIBCO Water and Ice Park (13.6 mi / 22 km)
  • Sauganash Golf Club (16.5 mi / 26.6 km)
  • Maxwelton Golf Club (16.6 mi / 26.7 km)
  • Wawasee Golf Club (18 mi / 29 km)
Natural features

Exploring the natural features in Middlebury

Whether you're looking for adventure or just want to take in the scenery, Middlebury is a great place to get outside. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • North Park (6.7 mi / 10.7 km)
  • Wellfield Botanic Gardens (14 mi / 22.6 km)
  • Oaklawn Terrace Park (16.8 mi / 27.1 km)
  • Lakeside Park (17 mi / 27.4 km)
  • Scidmore Park and Petting Zoo (18.8 mi / 30.2 km)
  • Hidden Marsh Sanctuary (20.3 mi / 32.7 km)
How to get there

How to get to and around Middlebury

Fly into Goshen, IN (GSH-Goshen Municipal), the closest airport, located 11.5 mi (18.5 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to South Bend, IN (SBN-South Bend Intl.), which is 31.3 mi (50.4 km) away.

How many vacation rentals are available around Middlebury?

Our 2021 property listings offer a large selection of 29 vacation rentals around Middlebury. From 27 house rentals to 7 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.