Holiday houses in Middlebury

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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 $130 AUD 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 and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Middlebury holiday rentals include Wi-Fi 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, 334 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 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.
Campervan/RV in Middlebury
4.96 out of 5 average rating, 144 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, 604 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
The exterior of The Joy House on Main showcases a historic porch with stylish rocking chairs and beautifully landscaped gardens. Inside, a cozy living area is highlighted by comfortable seating and natural light. Bedrooms feature relaxing designs, and the kitchen displays organized utensils and plants, enhancing the homey feel.
Home in Middlebury
4.98 out of 5 average rating, 85 reviews

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.

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
4.92 out of 5 average rating, 229 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
The cabin is constructed of warm wood, surrounded by lush greenery and tall pine trees. A welcoming front porch features two chairs and flower beds, inviting relaxation. Large glass doors provide views of the outdoor space, enhancing the connection with nature.
Cabin in Goshen
4.96 out of 5 average rating, 342 reviews

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.

Top Guest favourite
A modern guest house features a striking black exterior contrasted by natural wood detailing. Large windows allow ample light to filter in, while surrounding greenery and trees provide a tranquil environment. A covered porch extends from the side, adding to the outdoor living space.
Tiny home in Middlebury
5 out of 5 average rating, 45 reviews

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

Guest favourite
Loft in Middlebury
4.94 out of 5 average rating, 65 reviews

Haven Suites - “Apt. A” YOUR place of REST.

Step away from and escape to a place of rest Surrounded by birds. Chirping - sound of nature While enjoying this luxurious ** NEW! ** 1 bedroom, 1 bath with fold down couch , designed with your comfort in mind. .. This spacious retreat has another space available ForLarger groups. Can reach out .. another bed and bath with couch as well The unique layout is perfect for the get away you’re looking for ..! 10 mins to Shipshewana, 40 mins to ND, and 10 mins to downtown Middlebury

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
4.95 out of 5 average rating, 99 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
A cozy studio apartment features a comfortable bed with soft linens, a wooden coffee table, and a light-colored chest of drawers. Natural light filters in through a nearby window, illuminating the space. A green armchair is positioned in one corner, adding to the inviting ambiance.
Loft in Shipshewana
4.96 out of 5 average rating, 372 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
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 out of 5 average rating, 147 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!

Guest favourite
The spacious bedroom features a queen bed with crisp white linens, flanked by stylish lamps on either side. Two large windows allow natural light to fill the room, enhanced by blue curtains. A soft carpeted floor adds to the cozy ambiance.
Apartment in Middlebury
4.95 out of 5 average rating, 107 reviews

Quiet, rural apt w/lg yard-8mi to Shipshewana

Nestled in the quiet countryside between Middlebury and Shipshewana, this 2nd level apartment is the perfect place to recharge on your next getaway to Amish country. We offer a latge outdoor wpace with a newly installed pergola, firepit, swing and hammock for your ultimate relaxation. We offer a well-stocked kitchen, including a sink, refrigerator, countertop convection oven and microwave. You will love the options this space offers. NOTE: No stove

Popular amenities for Middlebury holiday rentals

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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