Photo by Ann Sair

Middlebury holiday lettings

We found 87 holiday rentals — enter your dates for availability

Discover a selection of 13 homes and other holiday rentals in Middlebury that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

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Travel to cosy Middlebury

The gardens and surrounding scenery provide a peaceful ambience to your holiday home in Middlebury. Travellers to this welcoming city praise the shopping, hiking and cycling. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday 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

Do you want to discover things to do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Middlebury has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Meadow Valley Golf Club (1.2 mi / 2 km)
  • Dutch Creek Farm Animal Park (5.8 mi / 9.3 km)
  • Wawasee Golf Club (18 mi / 29 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 traveller or just want to appreciate the scenery, Middlebury is a great place to get out in nature. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport to and around Middlebury

Fly into Goshen, IN (GSH-Goshen Municipal), the closest airport, located 11.5 mi (18.5 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into South Bend, IN (SBN-South Bend Intl.), which is 31.3 mi (50.4 km) away.

Frequently asked questions

What is the best area to stay in Middlebury when booking a holiday rental?
When considering a holiday rental in Middlebury, Indiana, a popular area to stay is the charming downtown district. This area is not only picturesque with its historic buildings and small-town charm, but it also offers a delightful selection of local shops and eateries. Nearby, you can explore the scenic Riverbend Park, which provides lovely walking trails and picnic spots, superb for enjoying the natural beauty of the region.

Another appealing neighbourhood is the area surrounding the Amish community, where visitors can immerse themselves in the rich culture and traditions of the local Amish population. Here, you can find unique handmade crafts and delicious homemade treats, which are a true highlight of the area.

In terms of holiday rentals, there are a variety of properties available in both districts, suiting different preferences and group sizes. Staying in these areas allows you easy access to local attractions, such as the Amish Acres, which is a delightful place to learn more about Amish life and enjoy various performances.
How much does it cost to rent a holiday home in Middlebury?
Prices for holiday 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 holiday 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.
Where are the best Middlebury ski resort rentals?
For skiing near Middlebury, the closest resort is likely the Swiss Valley Ski & Snowboard Area, located a short drive away. In the surrounding areas, particularly in nearby villages like Elkhart and Nappanee, travellers can find a variety of rental options suitable for those looking to enjoy a winter getaway. Many properties in these areas include family-friendly amenities such as spacious living areas, fully equipped kitchens, and sometimes even game rooms or entertainment systems, suiting groups after a day on the slopes.

In addition to these conveniences, rentals often feature outdoor spaces for relaxation, such as decks or patios, where guests can unwind and enjoy the crisp winter air. Some accommodations may even provide access to local trails for cross-country skiing or snowshoeing. The proximity to local shops and restaurants in Elkhart enhances the experience, allowing guests to easily explore dining options and other amenities.
What is the most popular type of holiday rental accomodation in Middlebury?
In Middlebury, holiday houses are the most popular type of holiday rental, with around 22 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or larger groups. Many also include outdoor spaces like patios or gardens, great for relaxation after a day of exploring. Additionally, there are several cottages and cabins that provide a quaint, rustic charm, often located in nature for a peaceful retreat. Apartments are also available, offering a convenient option for those seeking a more compact stay.
Are there any family house rentals in Middlebury?
In Middlebury, Indiana, there are twelve family-friendly house rentals available, making it an excellent choice for visitors seeking spacious rooms. The area features charming properties that often boast multiple bedrooms, generous living areas, and fully equipped kitchens, superb for preparing family meals together.

Many homes come with outdoor spaces where children can play, and some may include amenities such as game rooms for added entertainment.

Middlebury is known for its picturesque surroundings and a strong sense of community, with nearby attractions such as the Amish countryside and local markets offering great experiences.
Can I rent a holiday home with a pool or hot tub in Middlebury?
In Middlebury, Indiana, there are several holiday homes available for rent that come with pools and hot tubs. This charming town, known for its picturesque surroundings and close-knit community, offers a variety of options for those looking to enjoy a relaxing getaway. Many of these properties feature private pools, spacious outdoor areas, and hot tubs, superb for unwinding after a day of exploring the local sights.

Travellers can expect amenities such as fully equipped kitchens, comfortable living spaces, and outdoor seating areas ideal for gatherings.
Can I find long-stay holiday rentals in Middlebury?
A long-stay holiday 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 for travellers. The area is known for its serene countryside and charming small-town atmosphere, making it an inviting choice for families and pet owners alike. Many of these holiday rentals typically feature spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam freely.

In addition to the comforts of home, the surrounding area offers a variety of pet-friendly points of interest, including local parks and nature trails that are superb for walking dogs. The nearby Bonneyville Mill County Park is a lovely spot to explore, with scenic trails and open spaces, providing plenty of opportunities for outdoor activities with your furry friends.
Are there any remote work holiday rentals in Middlebury?
In Middlebury, Indiana, there are numerous remote work-friendly holiday rentals available, with around 32 options to choose from. These properties typically come equipped with essential amenities for those looking to work remotely, including free Wi-Fi in both the rooms and public areas, and designated workspaces or desks to ensure a comfortable work environment. Many rentals also offer additional comforts, such as fully equipped kitchens and spacious living areas, making them suitable for longer stays.

The town itself is known for its picturesque surroundings and community spirit, providing a peaceful atmosphere that can be conducive to productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Middlebury holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 rental amenities include kitchens, allowing guests to prepare their own meals, and decks or patios that provide outdoor spaces for relaxation and enjoying the surrounding scenery. Onsite parking is commonly available, making it convenient for those travelling by car. Additionally, many rentals offer coffee and tea makers, ensuring that guests can enjoy their morning brew at their leisure.
When is the best time to visit Middlebury for a holiday rental?
The best time to visit Middlebury for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts families and outdoor enthusiasts eager to explore the charming surroundings and partake in various local festivities. The warm summer days, typically ranging from 20 to 30 degrees Celsius, create a friendly space for outdoor activities such as hiking, biking, and enjoying the picturesque Amish countryside.

During this time, you can experience the unique culture of Middlebury, with its delightful shops, farmers' markets, and seasonal events that bring the community together. The lovely weather makes it superb for leisurely strolls through the town or picnicking by the nearby lakes.

If you're seeking a more budget-friendly option, consider visiting in December. This quieter month allows you to enjoy the serene beauty of Middlebury, with a chance to experience the festive holiday spirit through local events and decorations, all while avoiding the summer crowds.

Ultimately, your choice depends on whether you prefer the lively summer atmosphere filled with activities or the peaceful charm of winter.
How early should I book a Middlebury holiday rental?
Book your Middlebury holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Middlebury?
In Middlebury, Indiana, visitors can enjoy a variety of attractions that reflect the town's unique charm and heritage. The downtown area features quaint shops and local eateries, superb for leisurely strolls. One of the highlights is the Amish community surrounding Middlebury, where guests can explore local markets and experience traditional craftsmanship.

The nearby Bonneyville Mill County Park offers scenic walking trails, picnic spots, and the historic Bonneyville Mill, which is a great place for photography and enjoying nature. Additionally, the area is known for its picturesque countryside, making it ideal for outdoor activities like cycling and hiking.

For those interested in local culture, the Middlebury Community Public Library often hosts events and activities, and the town has an inviting space that makes it easy to immerse oneself in the local way of life.
Can I change or cancel my Middlebury home rental booking on Vrbo?
To find Middlebury holiday 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 cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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