Holiday rentals in Middlebury
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Middlebury
Guests agree: these stays are highly rated for location, cleanliness and more.
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
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.
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.
Tiny home log cabin at the pines
Nurture your most important relationships at this peaceful authentic log cabin, built in 2022, set halfway in the long lane of our 18 acre property. Enjoy privacy with the massive pine trees behind you. Relax on the front porch and watch the sunset beyond the horse pasture and cornfields. The cabin boasts Wi-Fi, TV screen w options,a soaker tub, queen bed, recliners with heating feature, a full kitchen stocked with pots and pans, a washer and dryer. Everything you need for a longer stay.
Amen Corner - A Modern Retreat in Amish Country
Welcome to this brand new private guest house in Middlebury, Indiana tucked quietly away in the heart of Amish country. Amen Corner offers the best of both worlds…modern amenities surrounded by nature’s beauty and amazing sunsets. - Enjoy a beverage on the back patio while watching birds or the neighboring horses - Cuddle up for your favorite series inside with bedroom & living room fireplaces - Peace and quiet can be found also if you’re looking to just relax and walk some of our trails
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).
Serenity Cove Peaceful Setting
Serenity Cove is located in the heart of Amish Country in a peaceful pond setting, surrounded by fields of corn and beans. This single wide mobile home has all the amenities of home. Sit on the front porch and enjoy the sounds of nature. Just a short drive to the town of Shipshewana where you can enjoy the MidWest's largest flea market and the MEC Center which hosts concerts and other events. College Sports fans you are just a short 50 minute drive to the Notre Dame Campus.
Private Lake+Fire Pit+Sauna+Kayaks | Pine & Paddle
Welcome to Pine and Paddle — the perfect place to unplug, recharge, and reconnect with nature by the lake. Unwind at this cozy lakeside tiny home, perfect for couples, friends, or solo travelers seeking peace, nature, and a hint of adventure near downtown Shipshewana. 🔥 Campfire pad w/ firewood + lake views 🛶 Kayaks + fishing poles + private dock ♨️ Wooden barrel sauna for ultimate relaxation 🌳 Private lake, beach, & outdoor games 🛏️ Sleeps 5 w/ full-size bunks + couch
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.
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!
Serenity Farmhouse-1 BR in Indiana Amish Country
Come visit the heart of Amish country and experience a stay in a beautiful farmhouse on a quiet road surrounded by farmland . Watch horse drawn buggies pass by and listen to the birds as you sip your coffee either on the front porch or side deck. Sunday mornings at 8am is a great time to be on the porch and watch the buggies pass on their way to church. This location is in between Shipshewana and Middlebury making it just minutes from either town.
| Hot Tub | Amish Farm Country | Pergola | Deck |
Backyard country living at its absolute finest!! Hot tub, back deck, patio, pergola, grill, pastureland, fire pit, open space – Welcome to your Home Away From Home! This newly/fully renovated 3 bed/2 bath ranch house in the heart of Amish country is ready for you to explore the abundant activities. Located right next door to a real working farm makes it ideal for your country getaway, and not to disappoint, Amish buggies pass by often!
Popular amenities for Middlebury holiday rentals
Other great holiday rentals in Middlebury
Secret Haven ~Jacuzzi~Wildlife~Private Trails~
Farm stay in Amish Country - 4 Bedroom 2 Bath
The Red Thread Retreat
Lakin' It Easy
Joy House on Main Luxe - Downtown Middlebury
Cozy Renovated Home / Modern Kitchen / Coffee Bar
Newly Renovated Home-Comfort in Quiet Shipshewana
Secluded Solar Amish Farm-Breakfast upon request!
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.
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 £68 per night before taxes and fees
Verified guest reviews
Over 1,260 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!
Destinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Columbus Holiday rentals
- Cleveland Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Detroit Holiday rentals
- Milwaukee Holiday rentals
- Lexington Holiday rentals
- Traverse City Holiday rentals
- London Holiday rentals
- Downtown Chicago Holiday rentals
- Warren Dunes State Park
- University of Notre Dame
- Potato Creek State Park
- 12 Corners Vineyards
- Grand Mere State Park
- Weko Beach
- Fort Wayne Children's Zoo
- Dablon Winery and Vineyards
- Four Winds Casino
- Blue Gate Restaurant & Bakery
- Studebaker National Museum
- Potawatomi Zoo
- Four Winds Field
- Howard Park
- Pokagon State Park
- Country Heritage Winery
- Morris Performing Arts Center
- Basilica of the Sacred Heart, University of Notre Dame
- St. Patrick's County Park
- Auburn Cord Duesenberg Automobile Museum
- Kalamazoo Valley Museum
- Allen County War Memorial Coliseum
- Blue Gate Theater