Family-friendly holiday rentals in Greencastle

Covered Bridge Cabin (on Big Walnut Creek)

Retreat and renew in this charming one-room cabin by Big Walnut Creek and Baker's Camp Covered Bridge. Fish, kayak, or swim; hike or birdwatch in a nearby preserve; read, write, find inspiration. With sweet-smelling poplar walls, the cabin offers a full bed by picture window, inflatable single mattress, small TV, writer's desk, AC, fans and baseboard heat, kitchenette, toilet, sink, outdoor shower (before first frost), small porch, grill, and a fire pit. (No wifi in cabin.) Simple and beautiful.

Peaceful apartment space in beautiful farm house

Our lovely farmhouse is minutes from Lake Lemon, Griffey Lake, Indiana University & many spots in Bloomington. Conveniently not far from I-69, we're 20 minutes away from Nashville. This is a basement apartment with private bedroom, private bathroom, large living/dining area, & kitchenette. Shared front door & ~10 steps inside main floor. The ranch is 50+ acres with 8+ acres of woods for hiking, pastures with cattle, a heated pool & patio area, & a beautiful front porch looking over the ranch.

A room with view - great location

This room is a good value. It is close enough to Indianapolis yet peaceful, clean, quiet, and private. We are: 7.1 miles (10 minutes) from Indianapolis international airport. 18 miles (26 minutes) from downtown Indianapolis, 17miles (20 min drive) from Indianapolis convention center and Lucas stadium. 35 miles (52 minutes) from Indiana University in Bloomington. ~3 miles from I-70. If interested in booking please answer our pre booking questions found at the beginning of the house rules.

Hideaway Hollow - A Woodsy Getaway

Hideaway Hollow is a cozy, private guest suite in Bloomington, Indiana. Located on the north side, it is just fifteen minutes from the heart of downtown Bloomington, IU stadium, and an hour from Indianapolis. Nestled in the forest, the suite offers a covered porch with a private entrance, a spacious living room, a kitchenette, and a master bedroom with a full bath. Suitable for up to four guests, come to enjoy the serenity of country living, the comforts of home, and easy access to the city.

Courthouse Square Loft

At the intersection of DePauw University and historic downtown Greencastle! Recently renovated, our spacious and modern Loft is located above Scoops Ice Cream Shop and overlooks Greencastle’s Courthouse Square Historic District. You’ll be just steps away from many fantastic restaurants, boutiques, and charming shops. Come and enjoy scenic Putnam County all throughout the year! We are a short walk from the DePauw campus and close to many covered bridges. Turkey Run State Park is a short drive.

Castle 853 - We aim to be the cleanest!

Very Clean, stylish and up-to-date, Bedford Stone, single level home. Fully furnished, all linens, towels, cookware included. Coffee and snacks are there for your stay. We are a 3 minute drive to DePauw University, Crown Industrial Park, and the Historic Downtown full of Fine Dining, Craft Beer & Wine, Music. 300 feet from People's Pathway. Located in the heart of Covered Bridge country. 40 minutes from Indianapolis including the International Airport and the Indianapolis 500 raceway.

Maria’s Haven

Welcome to “Maria’s Haven”💕 A beautiful cozy home in the heart of a beautiful small town. This home belonged to my mother, Maria, who passed away in 2020 to breast cancer. This home was truly her “Haven”. Take a walk to the local diner, museum, Gosport playground, local shops, or to our delicious Amish bakery. We are also just a few miles from the popular “Hilltop” restaurant as well as McCormicks Creek State Park. Our mission is to make you feel like you never even left home. ☺️

Peaceful Ctry Home 1 ac. Wlk to 3FatLabs. 3BR 2BA

Peaceful country home near 3 Fat Labs and Depauw University. Situated on beautiful and quiet 1 acre lot with fire pit. Relax on the back deck and enjoy view, visit Oakalla covered bridge or hike at nearby Depauw nature trails. Home has en suite master with King bed and open floor plan. Kids room with bunk, toys and pack n play. Bathtub in 2nd bathroom. Enjoy large selection of DVDs and games for kids and adults. Satellite TV and internet. Washer/dryer. Only 3.5 miles to Depauw.

The 1938 Barn

The 1938 Barn is located in the ❤ of Covered Bridge Country in Parke County. You will love the rustic charm of this converted hay barn built in 1938. Come relax by the camp fire or explore our many Covered Bridges and local State Parks. The farm also hosts Henry's Market, a market garden providing fresh meat and vegetables which makes summertime an excellent time to visit! Please note: There is NO WI-FI, NO CABLE. We have a selection of DVDs. Limited cell service, AT&T works best.

The Main Street Retreat-NO CLEANING FEES

Enjoy your time to simply get away or as a must need sleep over due to travel or work. Only 14 miles south of I70. A Dollar General Store, Subway and Gas Station are nearby. Ten minute drive south to Sullivan for Walmart, restaurants, and grocery stores. Fifteen minute drive north to Terre Haute for all the city attractions. County and State Parks are near by as well. Located in a great neighborhood on main street with privacy. Maximum of only four adults allowed per reservation.

Swans Nest

If you are looking for a place to get away from the stresses of life this is it. You can fish on our 10 acres lake, walk thru the woods or just relax on the porch swing. Only 5 minutes from the nearest town, 30 minutes from Terre Haute and 40 minutes from Indy. Front porch faces a walnut tree grove and back porch faces 10 acre lake. At least 3 State Parks are within 20 miles of this property. Also super close to the Parke County Covered Bridge Festival.

Carriage House 1 bedroom loft suite w/ fireplace.

Keep it simple at this peaceful and centrally-located loft. Carriage House Guest Suite is located in a quiet neighborhood just five blocks from the courthouse square. Spencer's historic downtown offers the restored Tivoli theater, restaurants, art galleries & shops. Two miles from beautiful McCormick's Creek State Park and 3 miles to Owen Valley Winery. A convenient 20 miles to downtown Bloomington & Indiana University.