Photo by Ann Sair

Middlebury vacation rentals

We found 61 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Discover a selection of 15 homes and other vacation rentals in Middlebury that are perfect for your trip. Whether you're staying in a vacation rental with your kids or with friends, you'll find the amenities you need and want, which might include parking and a fireplace. You'll be sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
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Travel to cozy 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. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Middlebury

Are you hoping to find top things to see and do while you're in the area? Venture out of your vacation home and check out everything that makes Middlebury a fun place to get away. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Dutch Creek Farm Animal Park (5.8 mi / 9.3 km)
  • Deutsch Kase Haus (2.7 mi / 4.4 km)
  • Elkhart Tactical Laser Tag (14.6 mi / 23.5 km)
  • Wawasee Golf Club (18 mi / 29 km)
  • Cedar Lake Golf Club (18.3 mi / 29.5 km)
  • South Shore Golf Club (19.8 mi / 31.9 km)

Exploring the natural landscape of Middlebury

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Middlebury is a great place to spend some time outside. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Wellfield Botanic Gardens (14 mi / 22.6 km)
  • Lakeside Park (17 mi / 27.4 km)
  • Syracuse Lake (17.3 mi / 27.8 km)
  • Corey Lake (17.8 mi / 28.6 km)
  • Lake Wawasee (19.1 mi / 30.8 km)
  • Diamond Lake (21.2 mi / 34.1 km)

Transportation 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 might consider flying into South Bend Intl. Airport (SBN), which is 31.3 mi (50.4 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Middlebury?

The most popular types of vacation rentals in Middlebury are houses. After something a little different? Vrbo has plenty of options to match our guests' unique needs, so you'll see vacation properties in all sizes, and for all budgets. The perfect fit is ready and waiting for you — grab yours today.

How much does it cost to rent a vacation rental in Middlebury?

Length of stay, property type and time of year are among the factors that can affect the price of a vacation home. Simply click on your dates of travel to find your perfect fit. From cozy chalets to expansive luxury villas, all Vrbo vacation rentals offer amazing value.

How much does it cost to rent a beach house in Middlebury?

Prices for beach houses in Middlebury differ depending on the type and size of the property and time of year you're traveling. Simply enter your travel dates into Vrbo and how many guests to view available options and prices. From there you can use the filters to narrow your search by ratings, amenities, nearby activities and more.

Are there pet-friendly vacation rentals in Middlebury?

Yes. There are. You'll have your pick of two vacation rentals that cater to pets in Middlebury. Lots of our pet-friendly vacation rentals even have an outdoor area for your four-legged pal to play around in, complimentary treats, doggie beds and proximity to parks and green space. Apply the "Pets allowed" filter to find a vacation home on Vrbo that's pawfect.

What are popular rental amenities in Middlebury?

When it comes to rental amenities that people prefer in Middlebury, a nearby river, a barbecue grill and a garden are the most popular. With Vrbo vacation homes, you'll enjoy options to fit your style and taste, whether you're vacationing with your partner, family members or even pets.

Are there vacation rentals in Middlebury that welcome kids?

Gather the whole crew for an adventure in Middlebury at one of our two family-friendly vacation rentals. A lot of these stays come with conveniences that are ideally suited to getaways with the little ones, such as dining rooms, bunk beds and swimming pools. Just click on the "Properties good for families" filter and decide on your favorite.

What are the top attractions for families in Middlebury?

Spend a family day out at Elkhart County Fairgrounds. This major attraction is situated near the center of Middlebury.

Are there vacation rentals with WiFi in Middlebury?

You can choose from two vacation rentals with WiFi in Middlebury. If you want to disconnect from daily life during your escape, but still need to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Middlebury?

Work out your travel dates and then make use of the filters to look for vacation rentals with ac in Middlebury on Vrbo. With two air-conditioned properties on offer here, you can look forward to a comfortable and cool stay.

How old do you have to be to rent a vacation rental in Middlebury?

The minimum age permitted can differ between properties on Vrbo, so double-check the rules of the vacation home in Middlebury you want to book. But normally, it's 16, 18 or 21.

How long can I rent a vacation rental in Middlebury for?

How long you can rent a vacation rental in Middlebury is up to the property. Simply enter your selected travel dates to see a list of options offering extended stays. With many creature comforts such as kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to get somewhere perfect to call your home away from home in Middlebury.