
House vacation rentals in Greencastle
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Top-rated house rentals in Greencastle
Guests agree: these houses are highly rated for location, cleanliness, and more.

Adorable Bungalow 3 blocks from the 1st TURN
Cozy bungalow that lives bigger than it looks! Affordable luxury all at a terrific price! Fully private duplex has 2 stories and basement. We do allow dogs only, however I would like to know the breed & how many are staying. We do have some special "rules" for our furry friends! The neighborhood is walkable to restaurants, and very safe! Speedway boasts a low crime. The airport is close & downtown is closer! 465 is just 1.5 miles to access 465. Please no cats, or other type of pet.

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 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.

Feels Like Home!
You will love our home. Read our reviews and see for yourself!! Enjoy a stylish experience at this centrally-located place. We offer a one bedroom and one bathroom house. The bedroom has a queen size bed and the sofa has a memory foam queen size pull out bed. We’ve added a desk in the dining room and a cute coffee bar in the kitchen. You can enjoy the enclosed front porch while relaxing in the rocking chairs. We have a full size washer and dryer located off of the kitchen .

My little Speedway house
Cozy and upscale bungalow located in the heart of Speedway, Indiana.. Enjoy a small, but polished bungalow built in the 1930s. 2 bedroom, fully stocked kitchen, fenced private yard, and great location to all things racing and Indy! 5 Short miles to downtown and a 15 minute drive to the convention center. 1 dog is welcome! (More with written permission) Please share a bit of the nature of your trip, your hometown, & breed of your dog. No cats or other type animals, please.

Captain Bill's Guest House/seasonal swimming pool
Welcome to Captain Bill's Guest Lodge at Cagels Mill Lake! This gorgeous home offers modern amenities in a countryside setting. Perfect for bikers, boaters, fisherman, and anyone looking to enjoy lake life. Our guests are welcome to join us poolside at the main house. Our private pool is open only to us and our listed guests at our two Airbnb units. We're located seconds from the boat ramp and a short drive to Cataract Falls and Lieber State Park. Pool is seasonal.

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.

5 Min IU, Parking, Chef's Kitchen, Sunroom
🏡 Spacious & Thoughtfully Curated Home ⚡️2 Miles: IU, Stadiums, DT, Golf, Lake & More!⚡️ Newly renovated with style, comfort & convenience in mind. Guests love the thoughtful touches, cozy ambiance and immaculate cleanliness. Whether you're visiting IU, here for business, or a relaxing getaway, you’ll find everything you need. ✨Early/late check-in/check-out — $25 (2-3 hrs) ❤︎ Add to your wishlist by clicking the ❤︎ in the top-right corner!

Luxury Lake House: Stay French Lake
This bright and airy 4 bedroom home is a destination getaway perfect for your family, friends, or business retreat. With new furniture, appliances, and décor this retreat is the perfect getaway or staycation for your leisure or business needs. Nearby Attractions: Queen of Terre Haute Casino, Griffin Bike Park, Fowler Park, Laverne Gibson Cross Country Course, Rose Hulman, Indiana State University, and The Mill Concert Venue

freshly renovated 1 bedroom home
This freshly renovated beautifully decorated 1 bedroom home located in a great neighbor hood, within minutes to ISU and rosehulman college. Grocery store, restaurants and golf course just blockes away. kitchen has all utensils, plates, cups, pots and pans if you wish to cook. two tv's with Wi-Fi and Netflix is provided. there is a washer and dryer. New queen size mattress and an air mattress for a good night's rest.
Popular amenities for Greencastle house rentals
House rentals with a pool

Family Getaway: Indoor Pool, Sauna & Arcade

Downtown Whitestown, King Suite & Pool

Peaceful country home by DePauw and Monon Bell!

LuxeVilla-Pool-GameZone-Sleeps14-Kid|PetFriendly

Amazing Spacious Luxurious Home - Sleeps Up To 16!

The Getaway House with Hot Tub and Pool

Pool ~ Hot tub~Game Room~Theater~15mi to DT Indy

Entire house in Speedway! ~Big Yard~King Beds
Weekly house rentals

Overnight on Main

Major Dunbar Home

1860’s Art House

Park Place

Tiny House Retreat!

Indulgence at DePauw

Clean, functional and charming home

Authentic Country Farmhouse on Pond / Greencastle
Private house rentals

Azul Abode

Peaceful Wooded Lake Cottage Retreat

The Cozy Canary

Home in Brazil

Stacie’s Mom’s with Infrared sauna!

Kozy Kove

Asbury Guest House

Raceway Hideaway-quiet spot near all things Indy!
Quick stats about house rentals in Greencastle
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Destinations to explore
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- Lucas Oil Stadium
- Indianapolis Zoo
- Eagle Creek Park
- 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
- Prairie View Golf Club
- Greatimes Family Fun Park
- Woodland Country Club
- Broadmoor Country Club
- Crooked Stick Golf Club
- Hopwood Cellars Winery & William Rose Distillery
- The Trophy Club
- Cedar Creek Winery & Brew Co.
- Oliver Winery
- Harrison Hills Golf Club
- Urban Vines Winery & Brewery
- Bridgewater Club
- Brown County Winery