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Greencastle places to stay

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Top-rated places to stay in Greencastle

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Loft in Greencastle

4.96 out of 5 average rating, 169 reviews

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.

Bungalow in Clinton

4.89 out of 5 average rating, 205 reviews

Small Town Bungalow

Welcome to peaceful small town life. Two-bedroom bungalow on quiet street, close to everything. Newly renovated. Fully furnished. Original hardwood floors, new tile bath, king master, daybed/trundle second, queen sofa bed in living room. Large country kitchen stocked with fresh non-GMO eggs. Desk with printer. Roku TV in living room. Wi-fi internet. Garage parking. Spacious well groomed yard with tire swing. Sun porch. Pets welcome. Clean, comfortable, ready to be your home away from home.

Guesthouse in Crawfordsville

4.96 out of 5 average rating, 524 reviews

Mimi's Country Cottage

Quaint, quiet and cozy cottage set in a tranquil park like setting with all the amenities of home. Close to Shades and Turkey Run State Parks. 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 the cottage. We clean the cottage in accordance with CDC guidelines. Pets are allowed on a case by case basis. Please contact us for pet guidelines.

Barn in Greencastle

4.91 out of 5 average rating, 23 reviews

Come Live The Barn Life In Town!

1 bed 1 bath unique red barn w/ sleeper couch + air mattress to accommodate up to 5 people! Experience the slow pace of the country life 3.6 miles from Depauw University. Imagine the peace & quiet from this location while roasting smore's in the chimenea from the front porch, but a quick 2.2 mile drive to all the restaurants and shopping! Features -Wifi -Washer/Dryer -Kitchenette -Coffee Bar -Walk In Shower (handicap accessible) -Air Mattress -Pull Out Sofa Bed -Walk In Closet -Keyless Entry

Guest suite in Rosedale

4.97 out of 5 average rating, 176 reviews

Getaway in the Country. Large Hot Tub and more!

Beautiful, large area-perfect for the relaxing getaway. Ground floor unit (2 story unit-upstairs available for additional charge, otherwise not rented except for the month of Oct. both units will be rented separately) Queen sz bed + queen sleeper sofa. 55 in TV w/Showtime. Tastefully decorated. Massage chair. We do have internet, but we are rural and it's spotty.. Large private hot tub. Several State Parks nearby. If needing another room, check out The Getaway 2 on AirBNB (the upstairs unit).

Guesthouse in Terre Haute

4.96 out of 5 average rating, 154 reviews

College Cottage

Centrally located to 3 colleges and 2 hospitals in a peaceful neighborhood, this cozy, open concept studio guesthouse is perfect for a short- or long-term stay. This newly renovated garage apartment to guesthouse requires no steps and features a spacious fenced in area for your pet. Creativity abounds in this uniquely decorated space. It features a king-sized bed as well as queen sized sofa sleeper. The kitchen is well stocked and has a coffee/tea bar for your enjoyment. Pets are welcome.

Cabin in Martinsville

4.91 out of 5 average rating, 438 reviews

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!

Guesthouse in Terre Haute

5 out of 5 average rating, 124 reviews

10th Street Studio

Welcome to 10th Street Studio! This unit is very spacious, clean, quiet and comfortable. It is located on a quiet street in the Collett Park neighborhood, just minutes to Union Hospital, ISU, and downtown. It is a perfect location for traveling nurses and out of town workers as well as overnight guest passing through town, or those visiting family, friends or students. There is no extra cleaning fees and discounts for weekly and monthly stays. I look forward to hosting you!

Home in Poland

4.96 out of 5 average rating, 178 reviews

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.

Guesthouse in Rockville

4.96 out of 5 average rating, 201 reviews

Hideaway Hollow

This is a fully furnished picturesque Amish-built cabin in beautiful and secluded Parke County, Indiana. The cabin comes complete with all amenities including full bath with shower, queen bed, A/C, dish TV, wifi internet and full kitchen. There is a large deck attached with a beautiful view of the swinging bridge and the woods. Cook out on the deck's gas grill and enjoy cool evenings by the fire pit (wood provided). Enjoy a nap in the shade in the hammock.

Home in Brazil

4.92 out of 5 average rating, 283 reviews

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.

Cottage in Terre Haute

4.96 out of 5 average rating, 288 reviews

The Cozy Cottage

For only $75/night (plus one time cleaning fee) you can enjoy The Cozy Cottage for all your travel needs. Whether you just need a great place to stay for a couple of nights or for several months, this home has it all. Pet Friendly with one car carport. Great workspace for the business traveler and nice space to just relax. Free Hi-Speed, Wi-Fi. Roku is the main source of TV. Home is located near several amenities and only a mile from Interstate-70.

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Popular amenities for Greencastle places to stay

Laptop-friendly workspace

Air conditioning

Stay near Greencastle's top sights

Bridges Craft Pizza & Wine Bar10 locals recommend

Walmart Supercenter9 locals recommend

Almost Home Restaurant8 locals recommend

DePauw Nature Park7 locals recommend

Starbucks6 locals recommend

DePauw University6 locals recommend

Other great vacation rentals in Greencastle

Home in Greencastle

4.98 out of 5 average rating, 48 reviews

Greencastle Retreat:Hot Tub Haven & Fireside Charm

Cabin in Bainbridge

4.96 out of 5 average rating, 51 reviews

Covered Bridge Cabin (on Big Walnut Creek)

Home in Greencastle

5 out of 5 average rating, 32 reviews

Convenient to 3 fat labs and The DePauw campus

Guesthouse in Crawfordsville

5 out of 5 average rating, 89 reviews

Red House Guesthouse

Home in Greencastle

5 out of 5 average rating, 4 reviews

Park Place

Barn in West Terre Haute

4.99 out of 5 average rating, 81 reviews

The Goat-el at Old 40 Farm

Home in Greencastle

4.86 out of 5 average rating, 57 reviews

Cozy family home near restaurants and DePauw

Cabin in Brazil

4.9 out of 5 average rating, 21 reviews

Purdy Hill Cabin

Quick stats about vacation rentals in Greencastle

Total rentals
40 properties
Total number of reviews
1.8K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Popular amenities
Gym, BBQ grill, and Laptop-friendly workspace

Frequently Asked Questions

Are there house rentals with a dedicated workspace in Greencastle?
Yes! Work meets play with ease at over 10 house rentals in Greencastle featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Greencastle have wifi?
Absolutely! We offer over 20 house rentals with wifi in Greencastle. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Greencastle?
Greencastle has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Greencastle?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore