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Holiday rentals in Middlebury

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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
An exterior view of the Wana House showcases the two-story structure, surrounded by green lawns and trees. A spacious yard is visible, with nearby barns and an inviting landscape reflecting a peaceful countryside setting.
Home in Shipshewana
4.97 out of 5 average rating, 148 reviews

The-WANA-House: Shipshe / Amish owned: 6 bed 2 ba

Experience a bit of the Amish lifestyle yet with a few modern touches. Disconnect from the digital world and embrace the joy of conversation, board games, and simply being present in the moment. Surrounded by picturesque fields, you'll wake up to the harmonious sounds of nature and a breathtaking view every morning. Owned by WANA Cabinet & Furniture (next door), the Wana House is a 2-minute drive to Shipshewana’s main strip and the MEC center. It’s a perfect place to visit w/friends and family!

Top guest favourite
Cottage in Middlebury
4.82 out of 5 average rating, 311 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
The spacious living area features arched ceilings and large windows, allowing natural light to fill the room. Comfortable seating is arranged around a central coffee table, with a flat-screen TV mounted on the wall. The adjacent kitchen includes stainless steel appliances and cabinetry.
Flat in Goshen
4.96 out of 5 average rating, 910 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.

Top guest favourite
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.
Flat in Middlebury
4.93 out of 5 average rating, 161 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 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.
Camper van/Motorhome in Middlebury
4.96 out of 5 average rating, 134 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, 570 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 a circular, dark-hued building is illuminated by warm string lights during twilight. A private hot tub and a fire pit with chairs are visible, while the surrounding natural landscape emphasizes the peaceful setting.
Farm stay in Vandalia
5 out of 5 average rating, 268 reviews

Lux, Hot Tub, Restore, Calm, Creekside, Escape

*Escape to your private couple’s retreat. *Whether sipping coffee at sunrise or star gazing, The Grain Binn is the perfect blend of rest and charm *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

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, 221 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
4.95 out of 5 average rating, 317 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 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, 341 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, 121 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 favourite
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, 407 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.

Popular amenities for Middlebury holiday rentals

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 $116 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,190 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Wifi availability

    10 of Middlebury holiday rentals include wifi 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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