Holiday rentals in East Enterprise

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Top-rated holiday rentals in East Enterprise

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Top guest favourite
A historic cabin is nestled among lush greenery, showcasing a log design. A covered front porch extends from the cabin, providing a shaded area. Steps lead from the garden filled with ferns and flowers down to the riverside, where tranquility can be enjoyed.
Cabin in Union
4.91 out of 5 average rating, 149 reviews

Rustic Cabin on the Ohio River.

If you're looking for marble countertops, this may not be your place. But if you’re seeking quiet, character, and a taste of how things used to be, with a modern twist, welcome to our 1800s-era cabin. Renovated in 2022, the cabin is comfy but you can expect creaky floors, original woodwork, and a few quirks that come with age. The cabin is authentic, and thoughtfully kept. You will have TV, wifi, central heat, air conditioning but expect to hear the water pump run and there is no dishwasher.

Top guest favourite
A welcoming porch is seen with white railings and wooden flooring, overlooking a lush green landscape. The horizon displays a vibrant sunset with hues of orange and purple, creating a serene ambiance for relaxation.
Guest house in Canaan
5 out of 5 average rating, 42 reviews

Amish Country Cottage

Escape to peaceful southeastern Indiana Amish country! The Amish Country Cottage is a small one-bedroom studio that is perfect for two people. Formerly a writer's office, this quiet space features a beautiful wraparound porch perfect for enjoying your morning beverage as the birds sing. The unique octagonal reading nook will make you want to curl up with the latest title by your favorite author. The property is a working farm and features a walking trail in the woods. NO Animals allowed.

Superhost
A spacious bedroom features a comfortable bed with white linens, complemented by a tufted bench at the foot. Exposed brick walls contrast with sleek modern appliances in the kitchen area, while warm wood flooring and soft lighting create a cozy ambiance.
Flat in Aurora
4.84 out of 5 average rating, 165 reviews

Studio Apartment w/ Beautiful View!

Come and stay a while in this charming and unique studio apartment. Located in the heart of historical Aurora, IN, you can walk to all the shops, parks and restaurants! Step out onto your private patio and enjoy your view of the Ohio River! It’s the perfect romantic getaway. We are also pet friendly so if you want to bring your furry friends we are happy to host them as well, just be aware that there is a $100 fee that covers our additional cost. Just add them with your guests at checkout.

Top guest favourite
A bubbling hot tub is positioned on a wooden deck, with a view of a gathering area featuring several white Adirondack chairs surrounding a fire pit. The background includes green trees and an expanse of open grass under a clear blue sky.
Cabin in Rising Sun
4.99 out of 5 average rating, 118 reviews

Cheerful 2 BR cabin on 48 acres with ponds/firepit

From the bubbling hot tub, take in the country air and tranquility at this breathtaking 48 acre (completely private) two bedroom, two bath cabin centrally located between the Ark and the Creation Museum. Enjoy a cup of coffee or glass of wine around the majestic firepit overlooking the rolling meadows. Enjoy pristine ponds (with LED fountains) to fish and swim. Watch deer and turkey roam the property. Hike the trails which include a frisbee golf course designed to take in the scenery.

Top guest favourite
The cabin showcases a rustic exterior made of natural wood, featuring a welcoming front porch with wooden railings. Surrounding foliage displays autumn colors, enhancing the serene setting. A driveway leads to a garage door, while steps ascend to the main entry of the cabin.
Cabin in Madison
4.98 out of 5 average rating, 787 reviews

Cabin on the Ridge

Welcome to Cabin on the Ridge, your tranquil retreat nestled in the scenic hills of Madison, Indiana. Just 25 minutes from downtown Madison, our cabin offers a perfect blend of rustic charm and modern comfort. Madison, awarded the “Best Small Town in the Midwest” by USA Today and the Great American Main Street Award, is a must-visit. Enjoy the historic architecture, boutique shops, and delightful eats, or explore Clifty Falls State Park. •Fast wifi •Roku TV/Streaming services •Keurig

Guest favourite
The cabin features a welcoming exterior with a large wrap-around deck, offering ample outdoor space. A set of stairs leads up to the entrance. Large windows allow natural light to brighten the interior. Lush green grass surrounds the cabin, enhancing its tranquil setting.
Cabin in Patriot
4.83 out of 5 average rating, 221 reviews

Goose Creek Getaway--A Classy Country Cabin

This well-furnished cabin is surrounded by 18 acres of privately owned fields and woods. A wrap-around deck with a hot tub (extra) provides striking views. Hiking trails, fire pit, gas grill, pond, laundry, Direct TV (3), internet, stereo, equipped kitchen and games all make for a fun country stay. Rising Star and Belterra Casinos are closeby, and a park/boat ramp on the Ohio is nearby. Rising Sun and Vevay are short drives, and the Arc and Creation Museum are both within 1 hour.

Guest favourite
The floating home is illuminated warmly, showcasing large windows that reveal the interior. A wooden dock lines the side of the houseboat, with a railing providing safety. The setting includes lush greenery in the background, enhancing the peaceful atmosphere.
Houseboat in Florence
4.91 out of 5 average rating, 203 reviews

Peaceful Houseboat off the Ohio River

This mermaid themed, boatel is located in a beautiful setting in a cove off the Ohio River. Drive to nearby towns and visit antique shops and restaurants in Vevay and Madison, Indiana. Clifty Falls is a great place to hike. Beltera Casino Resort is down the street and the marina is also close to Rising Sun, Hollywood Casino, and Sunset Grill on the water in Warsaw, Kentucky. Conveniently located close to The Neeley Family Distillery. Some have visited the Ark while staying here also.

Top guest favourite
Two ceramic swans are placed close together on a wooden surface, creating a charming focal point. The backdrop features a calm lake surrounded by lush greenery, enhancing the serene atmosphere of the setting.
Cottage in Crittenden
5 out of 5 average rating, 154 reviews

Lake Front w/ Pool! Between Ark & Creation Museum.

If you are looking to experience lake life, look no further! Our Guest House sits on the beautiful 140 acre Bullock Pen Lake. It's a great place to relax, or enjoy kayaking, paddle boating, paddle boarding and fishing. We have one of the best views of the lake. The Guest House is fully renovated and decorated with relaxation in mind. It has everything you would need for your stay. After all, the lake is where your worries fade and memories are made! (The pool is now OPEN!!!) 5/11/26

Top guest favourite
The modern treehouse is showcased with a yellow deck extending from the entrance, situated on a gravel driveway. Large windows invite natural light, while the surrounding trees add to the natural setting. The structure appears elevated, resting on concrete stilts.
Treehouse in Rising Sun
4.98 out of 5 average rating, 138 reviews

The Dibble Treehouse

Welcome to The Dibble Treehouse! This cozy haven accommodates 4 guests and boasts all the amenities for an unforgettable stay. Relax in the hot tub or sauna, gently swing in the suspended bed or hanging chairs, and savor meals at the outdoor picnic table. The full kitchen is equipped for your stay and the wrap around porch offers stunning views. Enjoy evenings by the fire pit or take in your favorite shows on the smart TV. Book this stay to fully recharge and reconnect with nature!

Top guest favourite
Farm stay in Vevay
5 out of 5 average rating, 17 reviews

Mimi’s Guesthouse | Cozy Farmstay Retreat

Slow down and unwind at Mimi’s — a peaceful countryside retreat in Switzerland County. Sip coffee on the porch at sunrise, relax by the fire table, enjoy open skies, and explore nearby Amish country favorites. Thoughtfully styled with original artwork, Mimi’s was created to feel restful and welcoming. A portion of each stay supports local giving. 🐐 We love giving our guests a chance to meet the goats. These visits are a special extra and cannot be guaranteed during every stay.

Top guest favourite
An open living area features a grey couch with red accent pillows facing a decorative fireplace. A large area rug covers the hardwood floor, while a ceiling fan hangs above. Kitchen appliances and cabinetry are visible in the background, enhancing the spacious feel.
Flat in Vevay
5 out of 5 average rating, 8 reviews

Historic Delaney's Saloon- Main Floor

Built in the early 1800's, Delaney's Saloon is a renovated main floor unit with ceilings that soar! Located just one block from Ogle Park and the scenic Ohio River, you’ll be within walking distance of many local attractions including the Vevay Art Center, the Switzerland County Historical Museum, antique shops, restaurants, & bars/ lounges. Vevay is also home to Kat Von D's tulip field and VonDLand Shoes. Madison IN, Creation Museum, and The Ark are within an hour.

Top guest favourite
A vast, grassy area is bordered by a fence, providing an open space. Lush trees dot the landscape, with a clear blue sky and scattered clouds overhead. The serene environment reflects the rural setting, inviting activities such as relaxation or exploration.
Farm stay in Glencoe
4.96 out of 5 average rating, 133 reviews

Shepherd House, amazing view, King bed, lux tub

Enjoy this beautiful, peaceful dwelling with space for everyone. Sit on the covered porch taking in the hillside view or watch goats and sheep romp around the farm. You can take a guided tour and be greeted by all the animals during the day and do a little star gazing at night. We are a 50 acre working farm that practices sustainable agriculture, raising the best meats in humane ways. You can grill some to try for yourselves or make smores at the firepit.

Popular amenities for East Enterprise holiday rentals