Vacation rentals in Middlebury, IN

16 available vacation rental offers

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Middlebury, IN vacation rentals
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Best Vacation rentals and Airbnb offers in Middlebury, IN

Compare Vacation Rentals for Families in Middlebury, IN

These family-friendly vacation rentals in Middlebury, IN offer spacious layouts and easy access to top city attractions.

Rustic Roots Cabin| 3bd/3ba Cozy/shipshewana/nd - Middlebury, IN
9.9 62 reviews
Middlebury, IN
06/27 – 07/04
$538/nighttotal: $3766 (7 )

Rustic Roots Cabin| 3bd/3ba Cozy/shipshewana/nd

1 2
cabin , Middlebury
This charming cabin sits just a short drive from Middlebury's downtown area and the shores of Lake Champlain, offering a peaceful escape in the scenic Vermont countryside. The cabin consistently receives excellent ratings for its cleanliness, location, and overall experience, making it a popular choice for travelers. This cozy retreat features a spacious layout that comfortably accommodates up to 10 guests, perfect for families or groups of friends. Enjoy modern amenities like air conditioning and a fully equipped kitchen, relax in the private garden, or take advantage of the outdoor recreation options, including a sport court for pickleball.
Family Farm Stay+buggy & Pony Rides + Firepit - Middlebury, IN
9.9 32 reviews
Middlebury, IN
06/27 – 07/04
$161/nighttotal: $1127 (7 )

Family Farm Stay+buggy & Pony Rides + Firepit

1 2
gîte , Shipshewana
This Shipshewana family farm stay, located minutes from downtown Shipshewana, offers a peaceful rural retreat near local attractions.
The one-bedroom, one-bathroom house sleeps six guests and features a fully equipped kitchen with a ceramic grill, a firepit, indoor/outdoor games, and access to home-canned goods for purchase, plus buggy and pony rides.

Best Middlebury, IN vacation rentals with parking

218 M² Apartment ∙ 3 Bedrooms ∙ 8 Guests - Middlebury, IN
Middlebury, IN
06/27 – 07/04
$255/nighttotal: $1785 (7 )

218 M² Apartment ∙ 3 Bedrooms ∙ 8 Guests

3 2
apartment , Middlebury
This fully renovated Middlebury ranch house offers a tranquil neighborhood setting near Middlebury and Shipshewana attractions, ideal for exploring Northern Indiana's Amish Country. This 2,350-square-foot home features three bedrooms, two bathrooms, a hot tub, fire pit, and backyard games, comfortably accommodating up to eight guests.

Frequently Asked Questions about vacation rentals in Middlebury, IN

  • Which walking or cycling routes are the best in Middlebury, IN?

    The Middlebury Greenway Trail is a paved, 3-mile trail that runs along the Little Elkhart River, perfect for walking or biking. You can also explore the scenic backroads around Middlebury on a leisurely bike ride, enjoying the rolling hills and farmland.
  • What are the best Airbnb and vacation rentals in Middlebury, IN?

  • What sports or outdoor activites can visitors enjoy in and around Middlebury, IN?

    Middlebury is a great place for outdoor enthusiasts! You can enjoy fishing, kayaking, and canoeing on the Little Elkhart River. The nearby Shipshewana Lake offers boating and swimming, and the area has several golf courses. For a more relaxed experience, visit the Middlebury Farmers Market.
  • What are the most popular Airbnbs in Middlebury, IN?

  • What other towns or cities can be easily accessed from Middlebury, IN?

    Middlebury is conveniently located near several other towns and cities. You can easily reach Elkhart, Goshen, and South Bend, all within a 30-minute drive. These cities offer a variety of attractions, including museums, theaters, and shopping.
  • What are the best vacation rentals with a pool in Middlebury, IN?

    The best vacation rental with a pool in Middlebury, IN is The Maple House.

  • What amenities are commonly available in vacation rentals in Middlebury, IN?

    Vacation rentals in Middlebury typically offer amenities like kitchens, laundry facilities, and Wi-Fi. Some rentals may have additional features such as hot tubs, fireplaces, or private yards. It's best to check the listing for specific amenities.
  • What are the best rentals for families and kids in Middlebury, IN?

  • What time of year is best to rent a vacation rental Middlebury, IN?

    The best time to visit Middlebury depends on your interests. Spring and fall offer mild weather and vibrant colors, while summer is ideal for outdoor activities. If you enjoy the holiday season, consider visiting during the winter for the town's festive events.
  • What are the best rentals or Airbnbs with a jacuzzi in Middlebury, IN?

    | Hot Tub | Amish Farm Country | Pergola | Deck | and Hot Tub|beauitiful Backyard Oasis|newly Renovated are the best vacation rentals or Airbnb with a jacuzzi in Middlebury, IN.

  • What are the local dishes in Middlebury, IN region?

    The region around Middlebury is known for its Amish cuisine. You can find delicious homemade pies, breads, and pastries at local bakeries. Don't miss the traditional Amish chicken dinners, often served with mashed potatoes, gravy, and vegetables. The area also has a strong German heritage, so you'll find some German-inspired dishes as well.

Destinations nearby

Choose the Right Vacation Rentals with a Terrace in Middlebury, IN

Enjoy a Middlebury, IN vacation rental with a balcony and stunning city skyline views for a truly memorable stay.

Countryside Amish Cottage Near Shipshewana W/ 2 Br - Middlebury, IN
9.9 129 reviews
Middlebury, IN
06/27 – 07/04
$133/nighttotal: $931 (7 )

Countryside Amish Cottage Near Shipshewana W/ 2 Br

2 2
house , Topeka
This charming countryside cottage is located near Shipshewana, a community just minutes away from the property, offering a unique glimpse into Amish life. The house boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This cozy cabin features two bedrooms and one bathroom, comfortably accommodating up to five guests. The property offers a range of amenities, including a vegetable garden, play structure, fire pit, horse stable, and paddock, allowing guests to immerse themselves in the peaceful Amish lifestyle.

Discover Pet-Friendly Vacation Rentals in Middlebury, IN

Experience a pet-friendly stay in Middlebury, IN with vacation rentals located steps away from city dog parks and walking trails.

The Hidden Gem-sleeps 18,hot Tub,40 Min Nd - Middlebury, IN
10 28 reviews
Middlebury, IN
06/27 – 07/04
$803/nighttotal: $5621 (7 )

The Hidden Gem-sleeps 18,hot Tub,40 Min Nd

1 2
apartment , Bristol
This 5-bedroom, 3.5-bathroom woodland retreat is located a quarter mile off the main road in Elkhart County, offering seclusion and proximity to Goshen, Elkhart, Middlebury, Shipshewana, the RV Hall of Fame, the Pottawattomi Zoo, and Notre Dame Stadium.
This fully furnished apartment accommodates up to 16 guests, featuring a game room with an arcade console, a secluded hot tub, and a back patio perfect for outdoor dining and wildlife viewing.
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