Photo by Ann Sair

Middlebury vacation rentals

We found 86 vacation rentals — enter your dates for availability

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.

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Find out more about Middlebury

Why visit Middlebury

  • Outdoor Adventures: Enjoy scenic parks, serene lakes, and beautiful nature reserves perfect for hiking and relaxation.
  • Charming Downtown: Explore quaint shops and experience the welcoming atmosphere of Middlebury's friendly locals.
  • Rich History: Discover engaging historical sites in and around Middlebury, offering a glimpse into the past.
  • Family-Friendly Activities: Find a variety of recreational options that cater to both families and romantic getaways.
  • Unique Accommodations: Choose from cozy cottages, rustic cabins, or spacious homes for a memorable stay.

Popular types of accommodation in Middlebury

Planning a getaway to Middlebury? You're in for a treat. Discover the charm of this picturesque destination by exploring our top vacation rental options, including houses, cozy cottages, and rustic cabins. Whether you're looking for a spacious house for rent or a monthly rental, Middlebury has something for everyone. Start your adventure today and find the perfect vacation home in Middlebury to make your stay unforgettable.

  • Houses: The top choice for visitors in Middlebury, these homes offer spacious accommodations ideal for families or groups.
  • Cottages: A charming option, cottages provide a cozy atmosphere perfect for a romantic getaway or a peaceful retreat.
  • Cabins: Nestled in nature, cabins are a fantastic choice for those seeking a rustic experience amidst the great outdoors.
  • Apartments: Convenient and stylish, apartments cater to travelers looking for a home-like setting in the heart of Middlebury.
  • Condos: Offering modern amenities, condos are ideal for those wanting a blend of comfort and luxury during their stay.**

Top attractions in and around Middlebury

Middlebury, Indiana, is perfect for outdoor enthusiasts and those seeking a romantic getaway, offering stunning scenery and various attractions. Visitors can explore urban parks, serene lakes, and beautiful nature reserves, making it ideal for families and those wanting a city experience. Whether you're looking to relax in nature or enjoy recreational activities, Middlebury has something for everyone to enjoy.

  • Stone Lake: A serene destination in Middlebury, Stone Lake is perfect for outdoor enthusiasts. Enjoy romantic strolls along the beach, picturesque scenery, and opportunities for fishing and boating.
  • Blue Gate Performing Arts Center: Located 6 miles away, this cultural gem hosts a variety of performances, showcasing local talent and professional acts, making it a must-visit for arts lovers.
  • East Park: This family-friendly urban park in Middlebury offers playgrounds, walking paths, and picnic areas, making it an ideal spot for relaxation and outdoor fun.

Things to do recommended for couples

Middlebury offers a charming escape for couples. Stroll hand-in-hand through the picturesque downtown, explore quaint shops, or enjoy a cozy dinner at a local bistro. Don’t miss a scenic bike ride along the trails, perfect for creating unforgettable memories together.

Things to do recommended for families

Families visiting Middlebury can enjoy a fun-filled day at the Amish Acres, where kids can explore farm life and enjoy craft activities. Additionally, the nearby Shipshewana offers unique shopping and entertainment options, including the popular Blue Gate Theatre for family-friendly shows.

Things to do recommended for groups

Explore the charming Amish countryside on a guided tour, savor delicious homemade treats at local markets, or take a scenic boat ride on the scenic rivers nearby. Enjoy group activities like pottery classes or farm-to-table dining experiences that showcase the region's unique culture.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Middlebury

If you're traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your preferences when searching. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Middlebury with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group activities. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Middlebury with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, think about how close you are to attractions that are friendly for families.
  • Taking your pets with you to Middlebury: For many families, a vacation wouldn't be the same without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Middlebury: If you're searching for vacation rentals with special offers for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Middlebury

Middlebury, Indiana, offers a charming blend of outdoor beauty and rich history, perfect for a romantic getaway or family-friendly adventure. Explore the quaint downtown area, where friendly locals welcome you to enjoy scenic parks and unique shops. Nearby cities and neighborhoods provide vibrant atmospheres, from sunny excursions to engaging historical sites. Whether you're seeking leisure or excitement, Middlebury and its surroundings promise an unforgettable travel experience.

  • Shipshewana: Located 6 miles from Middlebury, Shipshewana is a charming town that offers a delightful blend of romantic and family experiences. Known for its vibrant outdoor markets, this city is a haven for those who appreciate unique finds and local crafts. Visitors can explore the public market, catch a show at the local theater, or enjoy the beautiful scenery at nearby lakes and national state parks. The community often hosts events at its conference venue, making it a lively place to soak in the local culture.
  • Elkhart: About 14 miles from Middlebury, Elkhart is a city that thrives on outdoor beauty and scenic views. This destination is perfect for couples and families alike, offering a range of recreational areas for fun-filled days. Explore educational attractions like the historic college university, or catch a performance at one of the local theaters. The city is also home to picturesque lakes and sports facilities, making it an excellent stop for those seeking both relaxation and activity.
  • Goshen: Just 9 miles from Middlebury, Goshen is another delightful city known for its stunning landscapes and romantic ambiance. With a rich selection of recreational areas, it’s an ideal spot for outdoor enthusiasts. Visitors can immerse themselves in educational experiences at local institutions or enjoy theatrical performances. Close to national state parks and beautiful lakes, Goshen offers a perfect balance of nature and culture, making it a must-visit for anyone in the area.

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking an extended stay for even greater savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient area for you to plan new trips, manage your existing plans, or review and organize your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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)
  • Wawasee Golf Club (18 mi / 29 km)
  • Cedar Lake Golf Club (18.3 mi / 29.5 km)
  • Swiss Valley Ski Area (20.1 mi / 32.4 km)
  • Saint Joe Valley Golf Course (20.5 mi / 32.9 km)
  • Meadow Valley Golf Club (1.2 mi / 2 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:

  • Stone Lake (5.5 mi / 8.8 km)
  • Long Lake (9.3 mi / 15 km)
  • Baldwins Lake (9.5 mi / 15.3 km)
  • Heaton Lake (11.1 mi / 17.9 km)
  • NIBCO Water and Ice Park (13.6 mi / 22 km)
  • Wellfield Botanic Gardens (14 mi / 22.6 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 best area to stay in Middlebury, Indiana, United States of America when booking a vacation rental?
When looking for the best area to stay in Middlebury, Indiana, consider the charming neighborhoods that embody the town's unique character. One popular area is the heart of downtown Middlebury, where you'll find a delightful mix of quaint shops and restaurants. This central location offers easy access to attractions like the Amish Acres, which provides a glimpse into the local culture with its beautiful performances and historical tours.

Another great option is the vicinity around the scenic lakes, where you can enjoy outdoor activities such as fishing and kayaking. This area is superb for those looking to relax and immerse themselves in nature while still being close to local dining and shopping experiences. In terms of vacation rentals, you can find a variety of properties in both areas, accommodating different group sizes and preferences.
How much does it cost to rent a vacation home in Middlebury?
Prices for vacation rentals in Middlebury vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Middlebury to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Middlebury vacation house rentals?
You can find great discounts on house rentals in Middlebury on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Middlebury?
In Middlebury, vacation houses are the most popular type of rental, with around 11 available throughout the area. These properties typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Additionally, there are several cottages and cabins that provide a charming, rustic experience, often featuring outdoor spaces for relaxation and gatherings. Apartments are also available, offering a more compact option for travelers looking for convenience.
Are there any family house rentals in Middlebury?
In Middlebury, Indiana, there are some family-friendly house rentals available, with approximately 12 options spread throughout the area. This charming town, known for its picturesque landscapes and Amish heritage, provides a welcoming environment for families. Many of these homes offer spacious living areas, full kitchens great for preparing family meals, and outdoor spaces where children can play or families can gather for barbecues.

Visitors can explore the nearby attractions, such as the scenic Lakes of the Four Seasons and the local parks that offer picnic areas and walking trails. The town's quaint atmosphere is complemented by its proximity to attractions like the Amish Acres and local markets, where families can experience unique cultural offerings.
Can I rent a vacation home with a pool or hot tub in Middlebury?
In Middlebury, Indiana, there are several vacation homes available for rent that feature pools and hot tubs. This charming town, known for its picturesque landscapes and Amish heritage, offers a variety of accommodations suited for relaxation and leisure. Many of these rentals come equipped with private pools, hot tubs, and spacious outdoor areas, superb for enjoying the serene surroundings. Additionally, travelers can expect amenities such as fully equipped kitchens and comfortable living spaces, making them ideal for families or groups looking to unwind.
Can I find long-stay vacation rentals in Middlebury?
A long-stay vacation rental in Middlebury is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Middlebury?
In Middlebury, travelers will find several pet-friendly house rentals that cater to those traveling with furry companions. Many of these properties offer spacious layouts, fully equipped kitchens, and outdoor areas where pets can play and enjoy the fresh air. The charm of Middlebury is enhanced by its scenic surroundings, making it an inviting destination for families and groups seeking a comfortable stay.

While enjoying your time in Middlebury, you can explore nearby parks and open spaces that are great for walks with pets. The community is known for its picturesque landscapes and friendly atmosphere, making it a superb spot for pet owners looking to relax and unwind.
Are there any remote work vacation rentals in Middlebury?
In Middlebury, Indiana, there are some remote work vacation rentals available, with around 16 options to choose from. These properties cater specifically to those needing a conducive work environment while traveling. Expect amenities such as complimentary Wi-Fi, dedicated workspaces equipped with desk chairs, and access to printers in some units. Many rentals also feature comfortable living areas, fully equipped kitchens, and outdoor spaces, making them ideal for a balance of work and relaxation. The town itself offers a quaint atmosphere, with local shops and eateries just a short distance away, providing a nice break from work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Middlebury vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Middlebury with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Middlebury?
In Middlebury, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals. Many rentals feature decks or patios, providing outdoor space to relax and enjoy the surrounding scenery. Onsite parking is also a common amenity, making it convenient for guests with vehicles. Additionally, most properties come with a coffee or tea maker, ensuring that guests can enjoy their favorite morning beverages.
When is the best time to visit Middlebury for a vacation rental?
The best time to book a vacation rental in Middlebury is during the peak season from June to August. This vibrant period attracts travelers seeking to immerse themselves in the charming atmosphere of this quaint Indiana town. Visitors can enjoy warm summer temperatures, typically ranging from the mid-60s to mid-80s Fahrenheit, great for outdoor activities such as exploring local parks, hiking, or visiting the picturesque Amish countryside.

July stands out as the most popular month, where the town comes alive with festivals, farmers' markets, and community events that showcase the rich culture and traditions of the area. It's an excellent time for families and friends to gather, enjoy the outdoors, and create lasting memories.

For those who prefer a quieter experience, consider planning your visit in December. While it may be the low season, the holiday charm of Middlebury is enchanting, with festive decorations and cozy winter activities that offer a unique perspective of the town.

Ultimately, your ideal time to visit Middlebury will depend on whether you crave the vibrant summer activities or the peaceful, festive ambiance of the winter months.
How early should I book a Middlebury vacation rental?
Book your Middlebury vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Middlebury, Indiana, United States of America?
In Middlebury, Indiana, visitors can enjoy a charming blend of small-town attractions and natural beauty. The downtown area features local shops and eateries, where travelers can experience the town's unique Amish heritage. Nearby, the Essenhaus complex offers a delightful restaurant, bakery, and shops, all showcasing local craftsmanship and traditional cuisine.

For those interested in outdoor activities, the scenic Millrace Park provides walking trails, picnic areas, and a picturesque setting along the Elkhart River, great for a leisurely day out. Just a short drive away, the Bonneyville Mill County Park features a historic gristmill and beautiful landscapes that are great for hiking and photography.
Can I change or cancel my Middlebury home rental booking on Vrbo?
To find Middlebury vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Middlebury vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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