Vacation rentals in Greencastle

4.97 out of 5 average rating, 202 reviews

The exterior of Namaste Lofts is shown, highlighting the red brick façade and large windows with green awnings. Nearby sidewalk seating is visible, along with surrounding storefronts, creating a vibrant downtown atmosphere.

Loft in Greencastle

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.

4.91 out of 5 average rating, 149 reviews

A modern kitchen space is featured, showcasing an island with bar stool seating. Nearby, a decorative wall art piece adds color. A glass bookshelf displays various items, complemented by a dining table against the wall. Warm light enhances the inviting atmosphere.

Loft in Greencastle

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.

A cozy bedroom features a dark wood bed with clean linens and two pillows. A lamp sits on a nightstand beside the bed. A window with dark curtains allows natural light to filter in, and framed art is displayed on the wall.

4.98 out of 5 average rating, 123 reviews

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.

4.97 out of 5 average rating, 149 reviews

An exterior view of the home is captured, featuring a light gray facade and metal roof. Colorful flowers and pumpkins decorate the landscaped garden, complemented by a bench positioned under a tree. Neatly arranged windows provide an inviting look to the property.

Home in Gosport

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. ☺️

A dining area is featured with a dark wooden table surrounded by six chairs. Natural light enters through two windows, illuminating the space. The kitchen is visible in the background, fitted with white cabinetry and modern appliances.

4.93 out of 5 average rating, 106 reviews

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.

4.9 out of 5 average rating, 113 reviews

A view of the dining area is presented, featuring a wooden table set in the center beneath a pendant light. The floor is adorned with a patterned rug, surrounded by windows that allow for natural light. A sideboard can be seen against the wall.

Home in Farmersburg

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.

Superhost

A well-appointed kitchen features modern appliances, including a black refrigerator, with wooden cabinetry providing ample storage. A large island with bar stools invites casual dining. Natural light fills the space through multi-paned windows, enhancing the warm wood tones of the decor.

Home in Poland

4.94 out of 5 average rating, 223 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.

A spacious living area is illuminated by recessed lighting, featuring a large gray sectional sofa adorned with decorative pillows. A round wooden coffee table is centered on a textured area rug, while a television stands on a light wood console. The open layout connects to a dining area with modern seating.

4.96 out of 5 average rating, 23 reviews

Modern Cottage In Town

Enjoy a comfortable and relaxing experience at this centrally-located home just 0.4 miles from Depauw's campus! 2 bed, 1 bath adorable home walking distance to downtown, campus, restaurants & shopping. Quiet established neighborhood. Features (1) King bdrm, (1) quen bdrm -Blackout curtains -Wifi -Spacious family room w/smart TV -Close to everything Outdoor patio w/furniture to enjoy the peace & quiet The space Modern cottage home with a minimalist aesthetic.

4.98 out of 5 average rating, 249 reviews

A single-story cabin is framed by lush greenery, showcasing natural wood siding and a welcoming front porch. The porch features seating arrangements and decorative elements, while the pathway leads to a gravel driveway, enhancing the serene ambiance of the surrounding woods.

Cabin in Carbon

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!

5 out of 5 average rating, 142 reviews

A cozy living area features a dark gray sofa adorned with yellow and patterned throw pillows. A television is mounted on the wall, with a wooden entertainment center below. A lamp stands beside the couch, and a potted plant is positioned near a window.

Loft in Spencer

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.

5 out of 5 average rating, 394 reviews

Loft in Mooresville

Loft Apartment: Beautiful Farm and Country Views

This beautiful, over the garage private apartment is located in a wooded area across from our 94 acre farm. A very peaceful setting to wind down and enjoy the nature around you. Conveniently located 15 minutes from the airport and 30 minutes from downtown Indianapolis. A work space is also available that overlooks this beautiful farm!! Also perfect for couples or small families to enjoy some time in the country!

The home features a charming facade with a gabled roof and symmetrical design. Two American flags are displayed on the front. A well-maintained lawn surrounds the house, complemented by neatly trimmed shrubs. A inviting walkway leads to the entrance, flanked by wooden chairs.

4.98 out of 5 average rating, 194 reviews

The Monon Belle

Welcome to The Monon Belle, located at 522 East Washington Street in Greencastle, Indiana, the home of DePauw University. This neo-classical home was built in 1920 just blocks from Greencastle's historic Courthouse District. Its location is within easy walking distance to all points on the DePauw campus. This is the ideal home to gather with friends and family members while visiting DePauw and Greencastle.

Popular amenities for Greencastle vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Greencastle

4.91 out of 5 average rating, 23 reviews

The exterior of a single-story building is shown, featuring a welcoming wooden door with a glass panel. Large windows with white trim allow natural light to enter. A black awning extends over the entrance, and two red planters with greenery are positioned on the sidewalk.

Home in Cloverdale

Overnight on Main

5 out of 5 average rating, 20 reviews

A spacious living room features a rounded gray sectional sofa facing a flat-screen TV on a wooden stand. Natural light enters through a window, with a view of greenery. A wall with rustic wood paneling adds texture, complemented by a clock and plants.

Guesthouse in Rockville

Raccoon Lake Retreat

Superhost

A charming green two-story structure is viewed from the street, featuring a covered porch and decorative gables. A large tree is positioned in front, providing shade. A parking area with a vehicle is visible in the foreground, along with a walkway leading toward the entrance.

Apartment in Greencastle

4.8 out of 5 average rating, 10 reviews

The Carriage House

4.98 out of 5 average rating, 90 reviews

The cabin's exterior is characterized by a wooden frame and a green metal roof. A covered porch is furnished with two rocking chairs and surrounded by lush greenery. String lights are suspended above the seating area, adding a welcoming touch to the outdoor space.

Cabin in Brazil

Purdy Hill Cabin

4.99 out of 5 average rating, 73 reviews

A comfortable living area is highlighted by hardwood floors and wooden beam ceilings. A cozy sofa is positioned opposite a media console, which houses a television. Natural light enters through a window, complementing the soft tones of the furnishings and decor.

Apartment in Danville

The Cozy Cottage II

4.87 out of 5 average rating, 45 reviews

The exterior of a yellow cottage is visible, framed by greenery. A welcoming porch features hanging plants and a hammock. A pathway leads to a landscaped area with a fire pit and flower beds, while a garage is positioned in the background.

Home in Rockville

The Cozy Canary

5 out of 5 average rating, 10 reviews

A rustic log home is showcased with a stone chimney and a welcoming porch. The property features large windows, wood siding, and a spacious outdoor area, surrounded by lush greenery and landscaping, creating a serene and inviting environment.

Cabin in Greencastle

Cabin retreat

A historic farmhouse with a large wrap-around screened-in porch is set against a backdrop of autumn leaves. A gravel pathway leads to the main entrance, and several white Adirondack chairs are positioned on the lawn, inviting guests to relax and enjoy the surroundings.