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Holiday rentals in Middlebury

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Middlebury

  • Total holiday rentals

    Explore 10 holiday rentals in Middlebury

  • Nightly prices starting at

    Middlebury holiday rentals start at €104 per night before taxes and fees

  • Verified guest reviews

    Over 1,360 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Middlebury holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Middlebury rentals

  • 5 Average rating

    Middlebury stays are highly rated by guests – averaging 5 out of 5!

Top-rated holiday rentals in Middlebury

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Cottage in Middlebury
4.83 out of 5 average rating, 340 reviews

Stone Lake Cottage Middlebury IN Boat Fish getaway

Located on beautiful Stone lake in Middlebury, IN. Crafts Amish antique auction fish swim lake relaxing. Bedding, towels, and personals/toiletries are provided. 2 queens, 1 twin, 2 double beds. Includes 3 BR/4 baths (detached 3rd BR CLOSED in winter), room for 6-8, AC, Smart TV, streaming services , WiFi, fireplace, lake, pier, kayak, paddle boat, grill, fire pit, dishwasher, toys for swimming, fishing, and 5 miles from Shipshewana/Middlebury. Min primary guest age is 21. Motel hotel

Top guest favourite
A spacious living area features an open layout with a dining table, a comfortable sofa, and a white armchair. A wooden coffee table sits on a neutral-toned area rug. The kitchen is visible in the background, showcasing white cabinetry and a dining area with natural lighting.
Flat in Middlebury
4.93 out of 5 average rating, 177 reviews

The Farm Vista

Retreat and unplug in a quite country neighborhood in the heart of Amish country. The covered porch overlooks a farm and you can see a great sunset and often wildlife as well. The apartment itself is a walkout basement with a front entrance and large windows overlooking the farm and field across the road. This apartment offers all the comforts of home with two bedrooms, a pullout sofa bed, large kitchen, living room and bathroom. This retreat provides a chance to unplug and do things together.

Top guest favourite
A compact kitchen area is visible, featuring wooden cabinetry and a light-colored counter. A dining table with four upholstered chairs sits adjacent. Soft lighting and a decorative clock contribute to the welcoming atmosphere. The flooring is finished in a light wood look, enhancing the space's openness.
Camper van/Motorhome in Middlebury
4.96 out of 5 average rating, 162 reviews

1-bedroom RV, in a quiet spot for couples getaway

Enjoy the sounds of nature when you stay in this unique place. This unit is on the grounds of Teaberry Wood Products... In the heart of Amish country... Rise n Roll bakery is less than a 1/2 mile from our location. The Pumpkine Vine bike trail is about a mile away, the attractions in Shipshewana and Middlebury are within 4 miles. A safe place for your children… If you prefer to stay at one of our local campgrounds, we will set up our unit for $50.00 plus you would need to pay the campground.

Top guest favourite
A welcoming front porch features two rocking chairs positioned beside a small decorative table, adorned with bright pink flowers. Lush greenery is visible in nearby planters, while sunlit windows with green shutters complete the charming country setting.
Guest suite in Shipshewana
4.97 out of 5 average rating, 633 reviews

Picket Fence Farm Private Guest Retreat Suite

Stay in a 2nd story private suite in a modern farmhouse where we reside on a family farm in Amish country. Guests have the entire 2nd floor: 2 bedrooms, a private bath, and a sitting room. You can watch Amish buggies drive by while you rock on the front porch, access shared patio spaces or sit by a creek. We have cows, goats & chickens. We're in the heart of Shipshewana Amish/Mennonite community, minutes from downtown Shipshewana & all it has. An authentic, comfortable country getaway.

Top guest favourite
A spacious living area features comfortable seating arranged around a coffee table. A large television is mounted on the wall, and natural light filters in through the glass doors leading to a patio. Decorative plants add a touch of greenery.
Home in Shipshewana
4.97 out of 5 average rating, 129 reviews

The Frey House

PLEASE READ GUEST ACCESS BEFORE BOOKING..... Bring the whole family to this great place with lots of room for fun. Located just 5 minutes from Blue Gate Theater and the Michiana Event Center. Only 3 minutes to the down town shops which includes the Vanilla Bean Icecream shop. 45 minutes from Notre Dame. With in walking distance to the Pumpkin Vine bike trail. Wake up in the morning and make a fresh cup of coffee as you sit at the kitchen table watching the horse drawn buggies drive past .

Guest favourite
A new hot tub is featured on a spacious deck, surrounded by natural greenery. A cozy chair sits nearby, offering a relaxing place to enjoy the peaceful outdoor setting. Sunlight creates a bright atmosphere, highlighting the tranquil environment.
Home in Middlebury
4.93 out of 5 average rating, 240 reviews

HOT TUB | Beautiful Backyard Oasis|Newly Renovated

HOT TUB! There's a brand-new hot tub on this property that is ready for unlimited fun! This fully renovated 3 bed/2 bath ranch house in the heart of Amish country is ready for you to explore the abundant activities in northern Indiana. It is the perfect place for your stay in Middlebury and Shipshewana! It's in a tranquil neighborhood and close to everything in town. Enjoy the backyard oasis for an excellent relaxing time: hot tub, seating, fire pit (firewood provided), and backyard games.

Top guest favourite
Home in Middlebury
4.99 out of 5 average rating, 103 reviews

Peaceful Amish Country Home | Family-Friendly

Relax at our peaceful, clean, and family-friendly home in the heart of Amish Country. This three-bedroom, two-bath retreat features a spacious living room perfect for family time after a day of exploring. Enjoy quiet mornings, fresh country air, and easy access to Shipshewana Flea Market, Essenhaus, local concert venues, and Amish bakeries. Just 40 minutes from South Bend, it’s the perfect blend of a relaxing getaway and city events. Let us show you what Midwest hospitality means to us.

Guest favourite
A charming two-story house is situated on a spacious lawn, surrounded by trees displaying autumn foliage. An attached garage with a stone facade complements the home. The driveway leads up to the entrance, inviting guests to explore the peaceful surroundings.
Home in Middlebury
4.94 out of 5 average rating, 106 reviews

Home with loft, Shipshewana, Elkhart, Notre Dame

Whether you are on a weekend getaway, wanting to explore the lovely towns of Shipshewana & Middlebury, or in the area to enjoy a Notre Dame game the Back Porch is the perfect place for you. At the Back Porch, guests enjoy a dreamy interior with live plants and the peaceful nature out back. Guests can easily observe Amish country, the Shipshewana flea market (16 min), stroll through the beautiful quilt gardens of Middlebury (15 min), or cheer on a Notre Dame football game (40 min).

Top guest favourite
Loft in Shipshewana
4.96 out of 5 average rating, 394 reviews

Hidden Country Hide-A-Way

Come relax in our cozy, modern country, studio apartment. It is  equipt with a fully stocked kitchenette, private bathroom, comfortable living space, large screen tv and office work space.  Enjoy some of the most picturesque landscape Northern Indiana has to offer.  We are just a 10 min walk from Stone Lake and have kayak rentals available upon request.  We are conveniently located 8 miles from Shipshewana and Middlebury, IN and just a 40 minute drive from Notre Dame.

Top guest favourite
Home in Shipshewana
4.96 out of 5 average rating, 381 reviews

The Oasis in Shipshewana

Enjoy the benefits of a furnished home during your stay! The perfect spot to enjoy a quiet place yet very close to local attractions in Shipshewana. The Shipshewana Auction & Flea Market is within walking distance. This is an ideal house for families looking for an economical vacation stay. A large deck and backyard for you to enjoy the outdoors. Bring your bicycles and take a ride on the Pumpkinvine Nature hiking and biking trail nearby. No TV but no time to miss it!

Top guest favourite
A modern kitchen area is highlighted by a large central island with a white countertop. Exposed brick walls add character, while vintage signage provides a nostalgic touch. A cozy seating arrangement features a small chair and a fireplace TV setup against the wall.
Guest suite in Middlebury
5.0 out of 5 average rating, 175 reviews

Mullet's Speed Shop

Refresh and relax at this newly constructed guest suite! Mullet's Speed Shop is conveniently located just 3 minutes from the famous Das Dutchman Essenhaus Restaurant and Bakery, less than 10 miles from the quaint shops of Shipshewana, and an easy 40 minute drive to Notre Dame (for the football fans). Take a bike ride or a peaceful walk on the Pumpkinvine Nature Trail less than 2 miles away. Nestled in the heart of Amish country, enjoy the buggies passing by!

Top guest favourite
Home in Middlebury
5.0 out of 5 average rating, 101 reviews

Farm stay in Amish Country - 4 Bedroom 2 Bath

Come visit the The White Barn Inn! It is nestled in the heart of Amish Country where you can slow down and relax as you watch buggies pass by, see beautiful sunrises and sunsets and watch our animals grazing and playing in the field. Our animals will more than likely meet you at the fence hoping for a treat. We are located 1/4 mile from the Pumpkinvine Nature Trail. *** MAXIMUM NUMBER OF GUESTS IS 10 ***NO PETS !! *** NO SMOKING, ALCOHOL OR PARTIES!!

Popular amenities for Middlebury holiday rentals

When is the best time to visit Middlebury?

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Frequently Asked Questions

  • What are the best places to stay in Middlebury?

    Stays near the town center make it easy to access shops, markets, and walkable areas. Quiet, rural surroundings are also frequently suggested for those looking to experience Middlebury’s countryside atmosphere.

  • What are the best things to do in Middlebury with kids?

    Families often explore local parks, interactive farms, and the Pumpkinvine Nature Trail. Visiting area museums or hands-on craft shops can also provide fun, educational experiences for children.

  • What are some of the best things to do in Middlebury?

    Walk the Pumpkinvine Nature Trail, visit Krider World’s Fair Garden, and sample regional foods at local markets or cheese shops. Exploring area craft studios and learning about Amish culture are also popular activities.

  • How is the weather in Middlebury?

    Middlebury has cold, snowy winters around 17–36°F (-8–2°C), and warm, humid summers reaching 79–83°F (26–28°C). Rain is spread throughout the year, with spring and summer bringing the highest rainfall.

  • When is the best time to visit Middlebury?

    Late spring through early fall is often recommended for comfortable temperatures and lively outdoor activities. This period highlights blooming gardens, local markets, and community festivals in and around Middlebury.

  • What are the best places to visit in Middlebury?

    Krider World’s Fair Garden is often recommended for a relaxing stroll, while local cheese factories and markets let you explore regional flavors. The Pumpkinvine Nature Trail draws those interested in outdoor activities.

  • What are some hiking trails in Middlebury?

    You can explore the Pumpkinvine Nature Trail, which runs through scenic countryside and woodlands. Parks and nature preserves around Middlebury also have walking paths suited for different activity levels.

  • What are some family activities we can do in Middlebury?

    Try biking or walking the Pumpkinvine Nature Trail, visiting family-friendly farms, or relaxing at local parks. Craft demonstrations and seasonal community events also invite families to participate together.

  • What are some of the best day trip ideas from Middlebury?

    Explore Amish-related experiences, visit local markets, or discover small towns around the region. Nature areas, craft shops, and museums nearby are often recommended for a broader view of northern Indiana’s heritage.

  • Are there any pet friendly accommodations available in Middlebury?

    You can find a range of pet-friendly accommodations in and around Middlebury. Many hosts list pet policies, so it is often possible to travel with dogs or other companion animals.

  • What are some local tips for visiting Middlebury?

    Consider exploring Middlebury’s locally rooted shops and restaurants, and take time to appreciate the area’s traditional crafts. Respect local customs in Amish communities, and check schedules for markets or seasonal festivals.

  • What is Middlebury known for?

    Middlebury is known for its Amish heritage, local cheese producers, and the connection to the Pumpkinvine Nature Trail. Many visitors come to experience its traditional crafts, welcoming markets, and small-town atmosphere.

  • What are the best hidden gems to explore in Middlebury?

    Explore local antique shops, quiet stretches of the Pumpkinvine Nature Trail, or small independent bakeries for a taste of Middlebury’s charm. Pocket gardens and handcraft studios are also frequently suggested by returning travelers.

  • What are the best foods to try in Middlebury?

    Local kitchens often serve comfort dishes, homemade pies, and traditional baked goods reflecting Amish and Midwestern influences. Many visitors look for freshly made noodles, chicken dinners, and seasonal produce at local restaurants or markets.

  • What should I bring for a trip to Middlebury?

    Pack for changing weather—layered clothing, a rain jacket, and comfortable footwear are useful year-round. Outdoor activities call for sun protection and sturdy shoes, while winter visits often require warm coats, gloves, and hats.

  • What is the nightlife in Middlebury like?

    Middlebury is known for a calm, laid-back evening atmosphere with casual dining spots and community gathering places. Live music, small cafes, or occasional local events are the main evening attractions rather than late-night venues.

  • What are the most popular events or festivals in Middlebury?

    Middlebury frequently celebrates its agricultural roots with fairs and seasonal festivals, especially in late spring and summer. Nearby towns host similar gatherings featuring local crafts, music, and traditional foods.

  • Are there family friendly vacation rentals in Middlebury?

    Many vacation rentals in and around Middlebury are well suited for families, often featuring extra space, kitchens, and outdoor areas. Family travelers can filter for amenities such as yards, multiple bedrooms, or child-friendly furnishings.