Photo by Ann Sair

Middlebury vacation rentals

We found 73 vacation rentals — enter your dates for availability

Discover a selection of 16 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.

Vacation rentals with weekly discounts - Middlebury

Showing deals for:Nov 14 - Nov 21

Image gallery for Lakefront retreat, hot tub, beach, pontoon, treehouse, 2 min walk to restaurants

Kitchen
10 out of 10 rating
Exceptional
(11 reviews)

Lakefront retreat, hot tub, beach, pontoon, treehouse, 2 min walk to restaurants

Union, MI

10% off
Price is CA $496
CA $4,239 total
includes taxes & fees
Lakefront retreat, hot tub, beach, pontoon, treehouse, 2 min walk to restaurants

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Find out more about Middlebury

Find out more about Middlebury

Why visit Middlebury

  1. Scenic Outdoor Adventures: Middlebury is surrounded by beautiful lakes and parks, perfect for hiking, biking, and enjoying nature.
  2. Middlebury Tasting Trail: Explore local flavours with a leisurely walk downtown, sampling delicious treats along the way.
  3. Charming Accommodation: Enjoy a cozy stay in private vacation homes, rustic cabins, or the welcoming Middlebury Inn.
  4. Romantic Getaways: The picturesque scenery and tranquil atmosphere make Middlebury ideal for couples seeking a romantic retreat.
  5. Family-Friendly Activities: With a variety of attractions suitable for all ages, Middlebury offers fun for the whole family.

Popular types of accommodation in Middlebury

If you're looking for the perfect getaway in Middlebury, you've come to the right place! Our most popular vacation rentals include charming houses, cozy cottages, and rustic cabins. Whether you're seeking a relaxing spa retreat or the comfort of the Middlebury Inn, there's something for everyone. Explore nearby hotels and star-rated options to enhance your stay, ensuring a memorable experience in this picturesque town.

  • Houses: The top choice for visitors in Middlebury, these homes offer spacious and comfortable accommodations ideal for families or groups.
  • Cottages: A charming option, cottages provide a quaint and cozy atmosphere, perfect for a peaceful getaway.
  • Cabins: Nestled in nature, cabins are popular for those seeking a rustic experience with modern amenities.
  • Apartments: Offering convenience and flexibility, apartments are great for solo travellers or couples.
  • Condos: These properties provide a blend of luxury and comfort, often with shared facilities for added enjoyment.**

Top attractions in Middlebury

Middlebury, Indiana, is a charming destination perfect for outdoor and romantic getaways. Visitors can explore scenic lakes, urban parks, and event venues, offering a mix of family-friendly and city experiences. Don't miss the Middlebury Tasting Trail, a leisurely stroll downtown, and nearby scenic trails, all ideal for day trips. Whether you're seeking adventure or relaxation, Middlebury has something to offer every traveller.

  1. Michiana Event Center: Located 11.3km from Middlebury, this event venue exudes a professional atmosphere, perfect for conferences and business meetings. Its versatile spaces can accommodate various events, making it a hub for local gatherings.
  2. Blue Gate Performing Arts Center: Situated 9.7km away, this arts centre offers a taste of local culture through live performances, plays, and concerts, showcasing the artistic heritage of the region.
  3. Elkhart County Fairgrounds: About 12.9km from Middlebury, this fairground is a family-friendly destination featuring outdoor activities, seasonal fairs, and community events that bring locals and visitors together.

Things to do recommended for couples

If you're seeking a romantic getaway in Middlebury, don't miss Fruit Hills Winery, just 9.7km away. Enjoy the entertainment and charming atmosphere, perfect for couples looking to relax and connect over a glass of wine in a picturesque setting.

Things to do recommended for families

During your family vacation in Middlebury, Indiana, enjoy nature at Bonneyville Mill County Park and Hermance Park, both offering relaxation. For adventure, visit South Lanes Family Fun Center for exciting arcade games, perfect for a fun-filled day together.

Things to do recommended for groups

In Middlebury, groups can enjoy a performance at the Blue Gate Theater, explore the bustling Shipshewana Flea Market, and visit the local Deutsch Kase Haus for a taste of regional cheese. These experiences offer a delightful mix of culture, entertainment, and local flavours.

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

When planning your trip, whether you're traveling with a group, family, pets, or seeking extended stays, it’s important to prioritize your preferences. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Middlebury with a group: Think about how many bedrooms you require, as well as features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Middlebury with young kids: Traveling with young children can present some challenges. It's important to prioritize their comfort and safety, along with ensuring access to age-appropriate facilities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • 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 properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that both you and your pet feel completely at home.
  • Planning for a long term stay visiting Middlebury: If you're in search of vacation rentals offering discounts for stays of a month or more, 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 consider adding features like a parking space, a well-equipped kitchen, or even a private pool to enhance your search.

Where to stay in Middlebury

Middlebury, Indiana, offers a delightful escape for those seeking a cozy retreat or a romantic getaway. Surrounded by picturesque scenery and friendly locals, visitors can enjoy outdoor adventures and explore nearby historical attractions. Whether it's a family-friendly outing or a peaceful mountain view getaway, Middlebury provides the perfect backdrop for creating lasting memories. With its sunny weather and charming atmosphere, it's truly the ultimate destination for a refreshing vacation experience.

  • Shipshewana: Located 11.3km from Middlebury, Shipshewana is a vibrant city known for its rich Amish heritage and charming atmosphere. Visitors are drawn here for romantic getaways and outdoor adventures amid picturesque scenery. Enjoy the lively public market, where you can sample local delicacies and shop for handmade crafts. The area also offers excellent theatre performances and events that highlight the local culture. Nearby attractions include tranquil lakes and the breathtaking landscapes of a national state park, making it a perfect stop for nature lovers.
  • Goshen: Situated 14.5km from Middlebury, Goshen is a city that captivates with its stunning natural beauty and recreational opportunities. Known for its outdoor experiences and romantic settings, Goshen features various parks and a fairground, providing ample chances for family fun. Visitors can explore educational attractions and enjoy local events throughout the year. The scenic lakes and national state parks in the area offer breathtaking views and outdoor activities, making it a lovely destination for those seeking adventure and relaxation alike.
  • Bonneyville Mills: Just 6.4km from Middlebury, Bonneyville Mills is a quaint village that invites adventure seekers to explore its natural beauty. Known for its outdoor experiences and picturesque scenery, this village offers recreational areas and parks ideal for hiking, picnicking, and enjoying the outdoors. The public market showcases local artisans and fresh produce, enhancing the community feel. Nearby landmarks include a national state park, serene lakes, and scenic dunes, providing a perfect backdrop for exploration and photography.

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's innovative Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or easily view and organize your travel plans. You can find the properties you've saved and booked under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-ca/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:

  • Deutsch Kase Haus (2.7 mi / 4.4 km)
  • Dutch Creek Farm Animal Park (5.8 mi / 9.3 km)
  • Cedar Lake Golf Club (18.3 mi / 29.5 km)
  • South Shore Golf Club (19.8 mi / 31.9 km)
  • Swiss Valley Ski Area (20.1 mi / 32.4 km)
  • Saint Joe Valley Golf Course (20.5 mi / 32.9 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:

  • Stone Lake (5.5 mi / 8.8 km)
  • Long Lake (9.3 mi / 15 km)
  • Baldwins Lake (9.5 mi / 15.3 km)
  • Elkhart Environmental Center (12.3 mi / 19.7 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 when booking a vacation rental?
When considering a vacation rental in Middlebury, Indiana, the downtown area is an excellent choice. This charming neighbourhood offers a delightful blend of small-town charm and vibrant local culture. Staying here places you within walking distance of various quaint shops, cafés, and restaurants, allowing you to immerse yourself in the local lifestyle. One of the top attractions nearby is the Amish Acres, where you can explore the fascinating Amish heritage and enjoy traditional food and crafts. Additionally, the scenic Riverwalk Park provides a lovely setting for leisurely strolls, picnics, or simply relaxing by the water.

Another appealing option is the area around the local parks, such as the Middlebury Community Park. This region boasts several vacation rental properties that cater to families and larger groups. The park itself is a fantastic spot for outdoor activities, featuring playgrounds, walking trails, and sports facilities, making it an ideal location for those looking to combine relaxation with recreation.
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 travelling 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.
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 accommodation, with around 13 available throughout the area. These houses typically offer spacious living areas, multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxing after a day of exploring. Additionally, there are several cottages and cabins, which provide a charming and rustic atmosphere, superb for those seeking a more intimate experience. Many of these properties are set in picturesque surroundings, allowing guests to enjoy the natural beauty of the region.
Are there any family house rentals in Middlebury?
In Middlebury, Indiana, there are numerous family-friendly house rentals available, with around 13 options to choose from. This charming town is known for its picturesque landscapes and close-knit community, making it a lovely destination for families. Many of the properties offer spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces great for children to play safely.
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 or hot tubs. This charming town, situated in the heart of Amish country, offers a peaceful setting with easy access to local attractions. Many of the rentals come equipped with private pools, hot tubs, and outdoor spaces, superb for relaxation after a day of exploring the area.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Middlebury?
In Middlebury, Indiana, there are several pet-friendly house rentals available, making it a great destination for travellers looking to bring their furry friends along. Many of these vacation homes come equipped with amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.
Are there any remote work vacation rentals in Middlebury?
In Middlebury, Indiana, there are numerous remote work vacation rentals available, with around 18 options to choose from. This quaint town is well-suited for those looking to combine work and leisure, offering a peaceful atmosphere amidst beautiful surroundings. Many of these properties come equipped with essential amenities for remote work, such as high-speed Wi-Fi, dedicated desk spaces, and comfortable chairs. Some may even feature business centres that are accessible around the clock, along with additional conveniences like laptop workspaces and computer monitors. 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 travellers 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 kitchens, free Wi-Fi, microwaves, and cookware, dishware, and utensils. These amenities are commonly found in the rentals available in the area, allowing guests to prepare their own meals and enjoy a comfortable stay. Additionally, refrigerators are typically provided, making it easy for travellers to store food and beverages during their visit.
When is the best time to visit Middlebury for a vacation rental?
The best time to visit Middlebury for a vacation rental is during the summer months of June to August, with July being the peak month for travellers seeking adventure and leisure. This vibrant season is characterised by warm temperatures, typically ranging from the low 20s to mid-30s Celsius, making it ideal for a variety of outdoor activities. Visitors can enjoy biking, hiking, and exploring the beautiful surrounding countryside, all while soaking up the lively atmosphere that summer brings to this charming Indiana town.

During these months, Middlebury comes alive with local events and festivals, offering ample opportunities to engage with the community and experience the rich culture of the area. The warm weather and longer days mean you'll have plenty of time for sightseeing, whether it's visiting the picturesque Amish farms or taking a leisurely stroll through the quaint downtown area, filled with unique shops and restaurants.

For those looking to save a bit on their vacation rental, consider visiting in December. While this is a quieter time in Middlebury, the season brings its own charm with festive decorations and a peaceful atmosphere, superb for cosy getaways. You'll find that the town is less crowded, allowing for a more intimate experience as you explore local traditions and perhaps partake in some vacation events.
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.
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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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