Best Vacation rentals and Airbnb offers in Middlebury, IN
9.8 33 reviews
Middlebury, IN
06/27 – 07/04
$119/nighttotal: $833 (7 )
Secluded Solar Amish Farm-breakfast Upon Request!
1 2
house , Middlebury
This Amish farm stay near Middlebury, Indiana offers a secluded retreat convenient to Shipshewana's flea market and Notre Dame, with nearby parks and bike trails. The one-bedroom, one-bathroom house accommodates four guests and features a kitchen with a refrigerator, a garden, scheduled buggy rides, and optional home-cooked Amish meals, plus on-site hiking trails and horse pastures.
10 5 reviews
Middlebury, IN
06/27 – 07/04
$189/nighttotal: $1323 (7 )
Cozy 3 Bedroom Home In Middlebury
1 2
apartment , Middlebury
This family-friendly apartment is located in downtown Middlebury, offering a short walk to local parks and shops, and is 7 miles from Shipshewana. This 3-bedroom, 1-bathroom rental accommodates up to 6 guests and includes a kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, internet, and parking, with a washer and dryer in the basement and a garage available upon request.
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.
10 2 reviews
Middlebury, IN
06/27 – 07/04
$163/nighttotal: $1141 (7 )
Serene Sanctuary | Tiny Home #1 In Amish Country!
2 2
apartment , Shipshewana
This tiny home in Shipshewana, Indiana, is located adjacent to horse pastures and the town park, with a baseball field, playground, and the Pumpkin Vine Bike Trail directly across the street. This modern farmhouse-style rental accommodates up to four guests, featuring two Queen beds, a kitchenette with a stovetop, fridge, and microwave, plus a patio with a fire pit and a front porch.
10 66 reviews
Middlebury, IN
06/27 – 07/04
$256/nighttotal: $1792 (7 )
Hot Tub | Beautiful Backyard Oasis|newly Renovated
3 2
apartment , Middlebury
This vacation home in Middlebury is an excellent choice for travelers seeking a relaxing and comfortable stay. It's located 2.8 miles from Deutsch Kase Haus and within 9 miles of popular attractions like Bonneyville Mill County Park and Shipshewana Auction and Flea Market. The house features 3 bedrooms, 2 bathrooms, and a spacious 2350 square feet of living space, accommodating up to 8 guests. It boasts a fully equipped kitchen, air conditioning, a relaxing spa tub, and a private fenced yard with an outdoor barbecue grill. Guests can enjoy complimentary WiFi, a smoke-free environment, and free parking.
Middlebury, IN
06/27 – 07/04
$139/nighttotal: $973 (7 )
Chickadee’s Cabin
1 2
gîte , Middlebury
This Middlebury, Vermont rental is a secluded two-bedroom cottage near the town, offering wildlife viewing opportunities including birds, deer, and groundhogs. The 5-guest-capacity home features a kitchen, air conditioning, parking, one bathroom, and a campfire area for evening relaxation, providing a peaceful escape near Middlebury's attractions.
9.7 18 reviews
Middlebury, IN
06/27 – 07/04
$132/nighttotal: $924 (7 )
Whispering Cottage #3 | Shewana Tiny Home Village
1 2
apartment , Shipshewana
This studio apartment in Shipshewana, Indiana, offers direct access to the Pumpkinvine Nature Trail, located just 0.2 miles from local shops, markets, and attractions like the Amish Country Visitors Center and Blue Gate Theater. This accommodation provides a queen bed, a sleep sofa, a kitchenette with a mini fridge and microwave, Wi-Fi, air conditioning, parking, and an outdoor patio with a fire pit, accommodating up to two guests.
Middlebury, IN
06/27 – 07/04
$161/nighttotal: $1127 (7 )
Honey Bee.
1 2
apartment , Middlebury
This Middlebury apartment rental boasts stunning Stone Lake views, less than a mile from the public boat ramp. The one-bedroom, one-bathroom unit sleeps four, features a fully equipped kitchen with dishwasher, in-unit air conditioning, and offers access to kayak, fishing boat, and pontoon rentals (availability and fees apply).
Middlebury, IN
06/27 – 07/04
$815/nighttotal: $5705 (7 )
Lake Life At It's Best!
1 2
apartment , White Pigeon
This three-bedroom, four-bathroom lakeside apartment rental in White Pigeon, Michigan offers stunning lake views and is perfect for families. The 9-guest dwelling boasts a fully equipped kitchen, air conditioning, parking, internet access, and convenient lake access for swimming, boating, or fishing.
9.8 225 reviews
Middlebury, IN
06/27 – 07/04
$244/nighttotal: $1708 (7 )
Hot Tub | Beautiful Backyard Oasis|newly Renovated
3 2
apartment , Middlebury
This 3-bedroom Middlebury home is situated in a peaceful residential neighborhood, just a short drive from Shipshewana's famous flea market and Amish community. The home boasts a spacious layout, comfortably accommodating up to 8 guests, and features a fully equipped kitchen, a backyard with a hot tub and fire pit, and a basement with a ping pong table and basketball hoop.
9.8 32 reviews
Middlebury, IN
06/27 – 07/04
$123/nighttotal: $861 (7 )
The Down Under
1 2
gîte , Goshen
This secluded studio apartment is located on the east side of Goshen, offering a tranquil setting less than one mile from the Elkhart County fairgrounds and the Pumpkin Vine bike trail entrance, and within four miles of Goshen College and Goshen Hospital. This gîte accommodates up to four guests with one bathroom, features air conditioning and internet, and provides a private patio and secure bike storage, making it an ideal base for exploring Amish country or visiting the University of Notre Dame, approximately 20 miles away.
10 4 reviews
Middlebury, IN
06/27 – 07/04
$151/nighttotal: $1057 (7 )
Natural Nook | Tiny Home #2 In Amish Country!
2 2
apartment , Shipshewana
This apartment in Shipshewana, Indiana, is located next to horse pastures and the town park, offering direct access to the Pumpkin Vine Bike Trail. This 2-bedroom, 1-bathroom home accommodates up to 4 guests with a fully-stocked kitchen, air conditioning, Wi-Fi, and a porch with a fire table.
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.
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.
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
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?
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.
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.
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.