Vacation rentals in Middlebury

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Top-rated vacation rentals in Middlebury

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Cottage in Middlebury
4.82 out of 5 average rating, 318 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 favorite
The exterior of the cabin features a rustic wooden facade with white horizontal stripes. Green window shutters frame four windows, contributing to a charming and inviting appearance. A covered porch supported by wooden beams offers a welcoming entryway.
Cabin in Shipshewana
4.97 out of 5 average rating, 436 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 favorite
A spacious living area features an open layout with a dining table, a comfortable sofa, and a white armchair. A wooden coffee table sits on a neutral-toned area rug. The kitchen is visible in the background, showcasing white cabinetry and a dining area with natural lighting.
Apartment in Middlebury
4.93 out of 5 average rating, 162 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.

Top guest favorite
Camper/RV in Middlebury
4.96 out of 5 average rating, 136 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 favorite
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, 583 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 favorite
Farm stay in Vandalia
5 out of 5 average rating, 276 reviews

Lux, Couples Hideout, Creek, Private Hot Tub,

*Imagine soaking in your private hot tub under the stars while a gentle creek flows just steps away. You are surrounded by trees and natural beauty. *Situated on 70 acres with flowing creek *Pickle Ball court 1 mile from Binn *Fully stocked kitchen *Fireplace *Hot tub with towels provided * Firepit with firewood *Bird feeder for Bird lovers *King size bed with quality bedding *Forgot something? Got cha *In floor heat *Snacks *Walking trails *Good WIFI *Unplug to reconnect

Top guest favorite
The log cabin, surrounded by snow-covered ground, features a wooden facade with a stone base. A porch with railings and steps leads to large glass doors, allowing views of the wooded area in the backdrop. A fence runs in front, adding to the secluded atmosphere.
Cabin in Goshen
4.95 out of 5 average rating, 324 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 favorite
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, 348 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 favorite
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, 124 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!

Top guest favorite
A hot tub is situated under a wooden pergola, with an expansive view of rolling pastureland and an open sky. Sunlight filters through fluffy clouds, creating a relaxing atmosphere for guests to unwind and enjoy nature.
Home in Middlebury
4.95 out of 5 average rating, 263 reviews

| 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!

Top guest favorite
A charming log cabin features a welcoming facade with large windows framed by wooden accents. The entrance is accessed via a stone pathway lined with landscaped garden beds, showcasing lush greenery and colorful plants. Surrounding trees provide a serene, natural setting.
Cabin in Middlebury
4.99 out of 5 average rating, 417 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.

Guest favorite
A kitchen countertop is adorned with a wooden tray featuring an arrangement of fresh flowers and greenery. Beside it, two glasses filled with lemonade and garnished with lemon slices are positioned on a smooth, textured surface. Modern kitchen appliances are visible in the background.
Home in Middlebury
4.9 out of 5 average rating, 266 reviews

Mayberry on 8 In Amish Country Sleeps 12+

Family get togethers, Girlfriend shopping trips, Couples looking for a place to reconnect with friends...we look forward to providing a great place to make memories. The wraparound porch invites you to stay awhile in the heart of Amish Country. Hosts live onsite in Owners Suite, you have the entire house to yourselves! Booking allows exclusive use of all guest bedrooms, as well as all common spaces at Mayberry on 8.

Popular amenities for Middlebury vacation rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Middlebury?

    Middlebury has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Middlebury?

    Experience the best of Middlebury with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Middlebury?

    Yes! Work meets play with ease at over 10 vacation rentals in Middlebury featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Middlebury have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Middlebury. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Middlebury have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Middlebury. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Middlebury have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Middlebury. Enjoy a tailored experience with all the comforts you desire.

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 ﺩ.ﺇ331 per night before taxes and fees

  • Verified guest reviews

    Over 1,260 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Middlebury vacation 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!

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