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Middlebury vacation rentals

We found 29 vacation rentals — enter your dates for availability

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.
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Find the best place to stay — Middlebury

Charming, spacious home near towncenter amenities, resturants, trails and parks.

Sleeps 6 · 3 Bedrooms · 1 Bathroom
$145 avg/night
(25)

Escape to Amish country for some R&Rx.

Sleeps 6 · 2 Bedrooms · 1 Bathroom
$120 avg/night
(2)

⭐️CountryClassic❤️of Amish Country⭐️NewlyRenovated

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
$132 avg/night
(5)

Stone Lake Vacation Cottage in Middlebury, IN near I 80/90

Sleeps 8 · 3 Bedrooms · 4 Bathrooms
$170 avg/night
(5)

Wellington Lake Cottage in Middlebury, IN.

Sleeps 8 · 3 Bedrooms · 3 Bathrooms
$246 avg/night
(3)

Amazing sunsets, Lake Front Home, Waterfront, near Shipshewana Indiana, Exit 107

Sleeps 8 · 2 Bedrooms · 1 Bathroom
$129 avg/night
(60)

Search 29 vacation rentals

Top rated rentals — Middlebury
Stayed Apr 2021

Beautiful location, and a perfect experience!

Lisa was great with communicating, and everything she said about the property doesn't do it justice!! We were having a small gathering before my friend's wedding and needed a spot for 10 people. This house was exactly what we needed. Private, on a la...

Steve W.
Steve W.

Fishers, IN

Stayed Apr 2021

Awesome place

Exactly as pictured. Very clean. We came down for the honeyville quilt auction. So relaxing after a busy day. Lots of room to see all our purchases. The lake was so pretty and the sunrise was worth getting up for. Planning on booking for the next auc...

Patrice V.
Patrice V.
Stayed Apr 2021

Great home in the heart of Amish country.

This home was perfect for our family of six. We were in the middle of Amish country, which we had come to visit and while there we discovered the Pumpkinvine Trail which passes a block from the house. We walked to the famous Essenhaus restaurant and ...

Carlin K.
Carlin K.
Stayed Apr 2021

Wonderful cottage .

My sister and I had a wonderful time at this cottage.I have stayed in numerous rentals in Shipshewana over the years. This ranked as one of the best. It was immaculately clean, cozy and comfortable. We will definitely stay there again when in the are...

Connie S.
Connie S.

Southgate, Mi

Stayed Apr 2021

Great location, beautiful property!

We had a fantastic time at this property. Gorgeous location right on the lake, fantastic kitchen, very relaxing set up. The balconies upstairs and the deck downstairs are the perfect location for relaxing with a good book or playing a game. Extremely...

Antonia S.
Antonia S.
Stayed Mar 2021

Awesome getaway

My daughter and I wanted to unplug for a couple of days and this place was great. We enjoyed the fire pit even though it was windy and cold. It was very clean and well maintained. The only issue for us was the smell of the water, strong iron smell. O...

Brenda F.
Brenda F.

Athens, MI, USA

Stayed Mar 2021

Family Getaway

The cabin was great; it had everything we needed. We enjoyed the view of the lake, the hot tub, and room to eat and play some games. It took around 5 mins to get to the center of town, which had plenty of places for eating, shopping, and taking a hor...

Sara D.
Sara D.
Stayed Mar 2021

Rare, Amazing Find! Very Clean and Well Maintained!

My wife, 6 yr-old and 10-month old stayed here in the cabin for a week. We can't say enough good things about our stay here. Even though the cabin is almost 200 years old, there have been many updates to bring it to modern standards including nice ap...

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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

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.