Vacation rentals in Middlebury

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Top-rated vacation rentals in Middlebury

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Guest favorite

Home in Middlebury

4.93 out of 5 average rating, 147 reviews

Farm Country|Amish Country|Newly Renovated|

Welcome to your home away from home!! This newly/fully renovated 2 bedroom / 2 bathroom ranch house in the heart of Amish country is ready for you to explore the abundant activities in northern Indiana. This is not only a wonderful house, but the location of this property next door to a real working farm is what makes it ideal for your country getaway, where the Amish buggies will pass leisurely by the house. You can enjoy a relaxing evening by the firepit in the backyard (firewood is provided), or you can travel about. You are less than 5 minutes away from the famous Das Dutchman Essenhaus restaurant; 10 minutes from world renowned Shipshewana where there are shops, restaurants, the well known Flea Market and Blue Gate Theatre; 15 minutes to the Bonneyville Mill Park where you can watch the old fashioned grinding and enjoy hiking and lovely scenery. The Pumpkinvine Trails is only about 1 mile away where you can take a relaxing walk/bike-ride through the countryside. Nappanee has additional Amish culture with shopping, theatre, and dining. All this and more as you relax and enjoy this wonderful area full of culture and hospitality.

Nov 1 – 8

$151 per night

Guest favorite

Guest suite in Shipshewana

4.98 out of 5 average rating, 101 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)

Aug 23 – 30

$100 per night

Guest favorite

Apartment in Goshen

4.96 out of 5 average rating, 735 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.

Feb 26 – Mar 5

$72 per night

Guest favorite

Cabin in Shipshewana

4.97 out of 5 average rating, 317 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!

Aug 24 – 31

$112 per night

Guest favorite

Apartment in Middlebury

4.93 out of 5 average rating, 120 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.

Aug 29 – Sep 5

$92 per night

Guest favorite

Guest suite in Shipshewana

4.98 out of 5 average rating, 346 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.

Jul 18 – 25

$70 per night

Guest favorite

Cabin in Goshen

4.92 out of 5 average rating, 145 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.

Sep 10 – 17

$94 per night

Guest favorite

Cottage in Topeka

4.89 out of 5 average rating, 147 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.

Nov 29 – Dec 6

$89 per night

Guest favorite

Loft in Shipshewana

4.98 out of 5 average rating, 104 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.

Sep 8 – 15

$77 per night

Guest favorite

Home in Shipshewana

4.96 out of 5 average rating, 254 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!

Oct 7 – 14

$133 per night

Guest favorite

Apartment in Middlebury

4.97 out of 5 average rating, 113 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!

Jan 28 – Feb 4

$90 per night

Guest favorite

Cabin in Middlebury

4.99 out of 5 average rating, 195 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.

Dec 17 – 24

$170 per night