Vacation rentals in Middlebury
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Quick stats about vacation rentals in Middlebury
Total vacation rentals
Explore 10 vacation rentals in Middlebury
Nightly prices starting at
Middlebury vacation rentals start at $166 CAD per night before taxes and fees
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Over 1,360 verified reviews to help you choose
Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 of Middlebury vacation 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 vacation rentals in Middlebury
Guests agree: these stays are highly rated for location, cleanliness, and more.
Cozy 3 bedroom home in Middlebury
Relax with the whole family at this peaceful cozy home in downtown middlebury where you can relax on the back deck or a short walk to the park and downtown shops . We are a few miles from Essenhaus , pumpkin vine trail two blocks away for biking/ walking. The historic Krider Garden. Inviting Coffee shops, Danny’s diner. We are 7 miles from Shipshewana where you experience Amish country, blue gate restaurant, theatre ,Ben’s pretzels, flea market, Michiana Event Center. 35 miles from Notre Dame.
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
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.
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.
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.
Joy House on Main Luxe - Downtown Middlebury
Experience luxury at The Joy House on Main - a beautifully restored historical home from 1904. Now owned and operated by us, Wes & Chelsea, owners of Joyfully Said. Immerse yourself in the charm of the past while enjoying modern comforts. Located in the heart of downtown, you'll have easy access to the renowned Pumpkinvine Trail, the charming shops, and top-notch local restaurants. Only 10 minutes away from Shipshe, this is the perfect destination for a small-town getaway with loved ones.
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.
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).
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!
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!!
Cabin off 39 - Peaceful, private one bedroom cabin
Kick back and relax in this calm, stylish space. Nestled among the trees, it provides a quiet getaway from the chaos of life allowing you to recharge and renew. The main residence is approximately 400 feet from the cabin. The cabin is secluded and yet close to local attractions, restaurants, biking and nature trails. The Cabin has a total of 420 sq ft living space with 280 sq ft on the ground floor and a 140 sq ft bedroom loft.
Popular amenities for Middlebury vacation rentals
Other great vacation rentals in Middlebury
The Cozy Cottage on Main Street
Modern Amish Country Tiny Home w/ Outdoor Shower
Secret Haven ~Jacuzzi~Wildlife~Private Trails~
Serenity Farmhouse-2 BR
Rustic Roots | Middlebury Log Cabin | Shipshewana
Lemon Hill Amish Guest House
Irish Black Bear Cottage
Haven Suites - “Apt. A” YOUR place of REST.
When is the best time to visit Middlebury?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $205 CAD | $180 CAD | $164 CAD | $175 CAD | $218 CAD | $230 CAD | $193 CAD | $189 CAD | $177 CAD | $180 CAD | $209 CAD | $180 CAD |
| Avg. temp | -4 °C | -3 °C | 3 °C | 9 °C | 15 °C | 20 °C | 22 °C | 22 °C | 18 °C | 11 °C | 4 °C | -1 °C |
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.
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