
Family-friendly vacation rentals in Greencastle
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Greencastle
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.

NAMASTE Lofts - Downtown Greencastle!
Looking for peace and serenity in the heart of downtown Greencastle, welcome to Namaste Lofts! We provide 2 distinctively designed lofts that exude a sense of calmnessin the bustling downtown. Each unit reflects the architectural features from the 1800’s, but the eclectic design with a mix of urban & modern furnishings makes the lofts a one of a kind place to stay. Located on the north side of Greencastle’s downtown square, you are walking distance to all entertainment, and DePauw University.

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.

Heavenly Acres Farm and Learning Center
Experience a relaxing stay, spending time watching chickens happily foraging or barn animals as they graze in the pasture. Take a walk by the creek, taking in the country sunset.Enhance your experience by interacting with the animals during a farm tour or helping with daily chores. We also offer a variety of learning opportunities as we share how we process fiber, health care for animals or maybe a simple hay ride. Here at Heavenly Acres we want to provide you with a unique farm experience.

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.

The Goat-el at Old 40 Farm
If you enjoy unique spaces & love animals, this is the apartment for you. Stay in the most unique "barn" you'll find. This loft apartment includes a full bath & is shared with 20+ goats & other farm animals. You're sure to have a memorable stay. There is a small pond on the property & ample free parking. If you time your stay right you could join in goat yoga or another farm event! This barn is located just off I-70 & a short drive to several areas colleges, the casino, & entertainment!

Mimi's Country Cottage
Quaint, quiet and cozy cottage set in a tranquil park like setting with all the amenities of home. Ten minutes to Shades State Park and twenty minutes to Turkey Run State Park. A great place to stay for the Covered Bridge Festival. 15 minutes to Wabash College, 25 minutes to DePauw University, 45 minutes to Purdue. We live on site and our back door is approximately 600 ft. from from the Airbnb. At this time we do not allow pets. We clean the cottage in accordance with CDC guidelines.

Grandpa's Cabin at Heidenreich Hollow
Grandpa’s Cabin at Heidenreich Hollow offers exclusive lodging on our hilly 5 acre wooded property. We offer a peaceful getaway from life while being right in the middle of both Indianapolis and Bloomington! Our quiet rustic cabin has a loft bedroom with stair access that includes a King size bed, 2 twin beds and an air mattress. We have a spacious bathroom and a fully equipped kitchen to help you feel at home. Search YouTube for Grandpas Cabin at Heidenreich Hollow for a video!.

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.

Bridge-View Suite at Cataract Falls Lodge
Welcome to Cataract Falls Lodge at the entrance to the Cataract Falls State Recreation Area. A one minute walk from the lodge and you will be standing on the overlook of the most spectacular waterfall in the Midwest. The lodge has three private suits that can be rented individually or combination thereof. This unit, Bridge-View, sleeps 4 offering one bedroom, a great room with attached kitchenette, full bathroom and personal outdoor space overlooking the entrance to the park.

Parke County Dream Cabin
Come experience the serenity of country living and get away from the daily grind of everyday life. Come fish in our five-acre lake (catch & release only), paddle-boat, kayak, or stroll through the woods. A covered porch and seating lakeside for relaxing. Located close to Mansfield and Bridgeton, 30 minutes from Turkey Run State Park, and only 30 minutes toTerre Haute or Greencastle. Come explore everything Parke County has to offer! KIDS WELCOME!
Popular amenities for Greencastle family-friendly rentals
Family-friendly home rentals with a hot tub

Country vacationing everyone will enjoy!

Eagles Rise Cabin on Sugar Creek with hot tub

Cozy Cabin on Lake front with Hot tub & firepit

Luxe Retreat in the Woods~Theater, Gym, Hot Tub

Couples Getaway with Outdoor Hot Tub!

Cozy Lakeside Cabin at Lake Lemon

Private 4 BDRM house, 5 Miles from Downtown #4

Cozy Cabin Close to University 1
Family- and pet-friendly home rentals

Lil BUB's Really Nice Apartment - EAST

Cozy and Comfortable, great Fall destination!

Blue Lemon Bungalow - Quiet Getaway in Town!

Cozy Country Guest Suite

Cozy Bungalow/With Parking/Close 2 Downtown Indy

Strawbale Bungalow. Bloomington Indiana USA.

The Cozy Cottage

Main Cabin-Wilkins Mill Guest House
Family-friendly home rentals with a pool

Serene 1BR: Perfect Indy Stay

Peaceful country home by DePauw and Monon Bell!

Stylish Stay | Near Everything!

Cabin retreat

1 Sweet Retreat

The Getaway House with Hot Tub and Pool

Avon Farmhouse-Sleeps 14 Game Room, Hot Tub, Pond!

Stylish Basement wAmenities/ Lounge; Close to DT
When is the best time to visit Greencastle?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ727 | ﺩ.ﺇ716 | ﺩ.ﺇ742 | ﺩ.ﺇ735 | ﺩ.ﺇ885 | ﺩ.ﺇ735 | ﺩ.ﺇ731 | ﺩ.ﺇ760 | ﺩ.ﺇ826 | ﺩ.ﺇ742 | ﺩ.ﺇ808 | ﺩ.ﺇ602 |
| Avg. temp | -2°C | 0°C | 6°C | 12°C | 18°C | 23°C | 24°C | 24°C | 20°C | 13°C | 6°C | 1°C |
Quick stats about vacation rentals that are family-friendly in Greencastle

Total vacation rentals
Explore 20 vacation rentals in Greencastle

Nightly prices starting at
Greencastle vacation rentals start at ﺩ.ﺇ441 per night before taxes and fees

Verified guest reviews
Over 1,290 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Greencastle vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Greencastle rentals

4.9 Average rating
Greencastle stays are highly rated by guests—averaging 4.9 out of 5!
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- Lucas Oil Stadium
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- Indianapolis Motor Speedway
- The Golf Club at Eagle Pointe
- Brown County State Park
- The Fort Golf Resort
- Brickyard Crossing
- The Country Club of Indianapolis
- The Pfau Course at Indiana University
- River Glen Country Club
- Woodland Country Club
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- Greatimes Family Fun Park
- Crooked Stick Golf Club
- Broadmoor Country Club
- The Trophy Club
- Hopwood Cellars Winery & William Rose Distillery
- Cedar Creek Winery & Brew Co.
- Oliver Winery
- Brown County Winery
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- Bridgewater Club
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