
Holiday houses in Middlebury
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Top-rated holiday rentals in Middlebury
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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.

Lofty Spaces, entire upper level, 5 mi from town
Stay in our redecorated entire upstairs level with pass-coded private entry to come and go as you please. Queen bed in the primary bedroom, a double in the second bedroom. (2 cots can be set up for any youth). Full bath with tub and shower, TV room with Kuerig, microwave, mini frig, and back wood’s view. Relax on front porch. Short walk to Fairgrounds and Pumpkin Vine trail. Close by places to eat. Notre Dame is 45 mins away. Shipshewana -40 mins. 60 miles to Lake MI. 3 hr drive to Chicago.

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.

Best Couples Vacation, Private, Hot Tub, Creek,
*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

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.

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!

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

| 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!

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.

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 holiday rentals
Other great holiday rentals in Middlebury

Rustic Roots Cabin| 3bd/3ba Cozy/Shipshewana/ND

Lemon Hill Amish Guest House

The Red Thread Retreat

Serene Sanctuary | Tiny Home #1 in Amish Country!

Family Farm Stay+Buggy & Pony Rides + Firepit

Secluded Solar Amish Farm-Breakfast upon request!

Amish paradise

Irish Black Bear Cottage
Frequently Asked Questions
Are there family-friendly house rentals in Middlebury?
Middlebury has more than 10 family-friendly house rentals. 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 holiday rentals in Middlebury

Total holiday rentals
Explore 10 holiday rentals in Middlebury

Nightly prices starting at
Middlebury holiday rentals start at $126 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!
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- Warren Dunes State Park
- University of Notre Dame
- Potato Creek State Park
- 12 Corners Vineyards
- Grand Mere State Park
- Benton Harbor St Joseph Ymca
- Weko Beach
- Blue Gate Restaurant & Bakery
- Four Winds Casino
- Fort Wayne Children's Zoo
- Potawatomi Zoo
- Four Winds Field
- Dablon Winery and Vineyards
- Howard Park
- Studebaker National Museum
- Country Heritage Winery
- Morris Performing Arts Center
- St. Patrick's County Park
- Auburn Cord Duesenberg Automobile Museum
- Blue Gate Theater
- Basilica of the Sacred Heart, University of Notre Dame
- Kalamazoo Valley Museum





