Holiday rentals in Middlebury

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Top-rated holiday rentals in Middlebury

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Guest favourite

Guest suite in Shipshewana

4.98 out of 5 average rating, 125 reviews

Cozy Industrial Farmhouse Walkout Basement

A newly renovated basement guest suite in the heart of Amish Country. Enjoy playing pool and a 60"TV during your stay. 1 mile from town and 34 miles from Notre Dame stadium. Enjoy a morning walk around the block and campfire in the evening. Playset and in-ground trampoline. Private entrance. One queen bed with futon and/or air mattress. Living room with smart TV, WiFi, cozy elec. fireplace, AC, elec. heat. Kitchenette with fridge, microwave, coffee maker /griddle /toaster oven. (No kitchen sink)

Guest favourite

Rental unit in Goshen

4.96 out of 5 average rating, 795 reviews

Half-Moon Cottage

Enjoy privacy in this beautifully handcrafted cottage with arched ceilings. The cottage is 2 miles from downtown Goshen - a vibrant small town with restaurants and shops. It's 1 mile from Goshen College, 45 minutes from Notre Dame and 25 minutes from the Amish town of Shipshewana. The cottage is beside a fruit, nut and berry orchard and gardens. It's adjacent to a city bike trail that links to the Pumpkinvine nature/bike trail. It's close to a train crossing (with whistle) and a busy street.

Guest favourite

Cabin in Shipshewana

4.97 out of 5 average rating, 367 reviews

Log Cabin

Are you looking for a quiet, relaxing and peaceful place to stay? Look no further, this little cabin is all that and more! These pictures do not do the cabin justice, we have heard this from so many guests that have stayed at our cabin! You will not be disappointed with your stay at our cabin. The kitchen is equipped with a stove, microwave, refrigerator and dishwasher. A front and back porch with beautiful views to drink a cup of coffee, read a book or relax! We hope you will come stay soon!

Guest favourite

Guest suite in Shipshewana

4.97 out of 5 average rating, 429 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.

Guest favourite

Home in Middlebury

4.91 out of 5 average rating, 152 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.

Guest favourite

Cabin in Goshen

4.95 out of 5 average rating, 202 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.

Guest favourite

Cottage in Topeka

4.9 out of 5 average rating, 173 reviews

Honeyville Cottage

Escape from the hustle of daily life in the heart of Amish country. Step into this quaint cottage and leave your worries at the door. Soak your cares away in the cast iron claw foot tub or relax on the patio watching the neighbors horses run. Bicycles are available for a stroll through back country roads. Play games around the kitchen table. Take a trip into town for fresh baked Amish goods, a traditional Amish dinner or shopping. At night you can grab a blanket and lay under the stars.

Guest favourite

Tiny home in Shipshewana

4.91 out of 5 average rating, 113 reviews

Minimalist Tiny house on a quiet lake

Enjoy a fall trip with a relaxing stay at this cozy tiny house located just a short trip from downtown shipshewana With a beautiful campfire pad on the back patio overlooking the lake , kayaks to take out for a relaxing morning ride or some fishing ( keep your eyes open for eagles and ospreys ) playing games with friends inside the house, reading a book you’ve been waiting to indulge in or heading to town for a concert , shopping or dinner you’re sure to have a wonderful time.

Guest favourite

Loft in Shipshewana

4.98 out of 5 average rating, 188 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.

Guest favourite

Rental unit in Middlebury

4.97 out of 5 average rating, 147 reviews

RV's, Amish, and Notre Dame, Oh My!

Located in small town Middlebury this open, bright, spacious 2 bedroom duplex is located perfectly to enjoy many area activities whether its enjoying a Nortre Dame game or visiting the largest Flea Market with lots of local Amish crafters. Local restaurants and breweries, as well as being near larger restaurants and shopping opportunities, makes this a great location. With beautiful Michigan lakes being only a short drive away makes this a great getaway!

Guest favourite

Guest house in LaGrange

5 out of 5 average rating, 121 reviews

Bird’s Nest Air BnB

Keeping it simple at this peaceful and centrally-located family farm. Within two miles of the famous Shipshewana Auction & Flea Market, Blue Gate Restaurant and Performing Arts Center. The Michiana Event Center which is also Located in Shipshewana has many attractions. We are located in the middle of a small, quiet farming community with all Amish neighbors, so be ready to listen to the clipclop of horses going by. Enjoy the peaceful country sunsets.

Guest favourite

Cabin in Middlebury

4.99 out of 5 average rating, 264 reviews

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.