Holiday houses in Greencastle

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Top-rated holiday rentals in Greencastle

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Guest favourite
A modern kitchenette features sleek dark cabinetry and a polished granite countertop. Open shelves display decorative items and glassware against a rustic exposed brick wall, while a small coffee station is set up with various coffee pods.
Loft in Greencastle
4.96 out of 5 average rating, 215 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.

Top Guest favourite
A dining area features a round wooden table surrounded by transparent chairs, complemented by plush white seat covers. A modern chandelier hangs from the ceiling, illuminating the space. The room showcases a combination of hardwood flooring and black accent walls, with large sliding glass doors leading outdoors.
Home in Greencastle
4.98 out of 5 average rating, 101 reviews

Modern 4 Bed Home On Golf Course Close To Campus +

4 bedroom, 2 bath-master w/shower guest ba w/tub & shower ranch home w/ 5th hole of the golf course as your view & literally steps from patio! Minutes from campus, restaurants & shopping. Quiet established neighborhood. (1) King bdrm, (2) bdrms w/full bed and (1) office/bedroom w/fold down couch. -Blackout curtains -Wifi -Spacious family room w/smart 75 in TV -Close to everything Outdoor patio w/furniture to enjoy the golf course views. Depauw themed basement w/ sauna, pool & poker tables

Top Guest favourite
Loft in Greencastle
4.92 out of 5 average rating, 156 reviews

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.

Top Guest favourite
Cabin in Unionville
5 out of 5 average rating, 205 reviews

Summer Escape: 40 Acre Forest Spa Trails & Boating

Summer Forest Reset🌳🐿 Rejuvenate in 2 bedrooms featuring king-sized beds 🍖☕️ BBQ shed & Coffee bar 🔥🛀 Fire pit & Hot tub Enjoy the best of both worlds: Secluded luxury with on-site trails or 15 minutes from Nashville’s artisan charm and Brown County State Park (pass included). Spend a day boating on Lake Lemon with a 10% discount code or enjoy the excitement of Brown County Dragway "Outlaw Style Racing " Note: As an active ridge top, occasional host sightings or construction may occur.

Top Guest favourite
Home in Greencastle
4.98 out of 5 average rating, 133 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.

Superhost
Home in Greencastle
4.89 out of 5 average rating, 112 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.

Guest favourite
The rustic barn is set against a vibrant sunrise sky, showcasing a mix of pink and orange hues. Lush green grass surrounds the barn, with farm equipment visible nearby. Trees and open fields fill the background, reflecting the charm of the rural landscape.
Barn in Rockville
4.79 out of 5 average rating, 141 reviews

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.

Top Guest favourite
A quaint one-room cabin nestled in a lush green forest, featuring a welcoming front porch with two blue chairs and a small table. The wooden structure is complemented by natural surroundings and has steps leading up to the entrance, creating a rustic yet inviting appearance.
Cabin in Bainbridge
4.94 out of 5 average rating, 108 reviews

Covered Bridge Cabin (on Big Walnut Creek)

Retreat and renew in this charming one-room cabin right 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 a picture window, small TV, writer's desk/library, AC, fans, baseboard heat, kitchenette, toilet, sink, outdoor shower (before first frost), small porch, grill, and a fire pit. (No wifi in cabin!) Simple and beautiful.

Top Guest favourite
A wooden deck provides an outdoor seating area with a circular table and several chairs. Lush greenery surrounds the tranquil lake, reflecting the clear blue sky and distant trees. A wooden staircase leads down to the water's edge.
Home in Brazil
4.93 out of 5 average rating, 373 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.

Top Guest favourite
Cabin in Carbon
4.98 out of 5 average rating, 282 reviews

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!

Top Guest favourite
Loft in Mooresville
5 out of 5 average rating, 424 reviews

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!

Top Guest favourite
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.
Home in Greencastle
4.99 out of 5 average rating, 204 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 holiday rentals

When is the best time to visit Greencastle?

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Frequently Asked Questions

  • What are the best places to stay in Greencastle?

    Greencastle has stays in historic neighborhoods near downtown, options close to DePauw University, and rentals around local parks. Guests seeking quiet surroundings can find vacation homes in residential areas.

  • What are the best things to do in Greencastle with kids?

    Kids can explore playgrounds in city parks, join library programs, and visit educational exhibits at campus museums. Seasonal festivals and hands-on art workshops are frequently suggested for families.

  • What are some of the best things to do in Greencastle?

    Explore public art around downtown, stroll through campus gardens, and enjoy live performances at cultural venues. Outdoor enthusiasts can wander local trails or relax in city parks.

  • How is the weather in Greencastle?

    Greencastle experiences cold winters around 21–36°F (-6–2°C), with ample rainfall and snow. Summers are warm, reaching 66–85°F (19–30°C), and spring brings mild temperatures with increased rain and blooming landscapes.

  • When is the best time to visit Greencastle?

    Late spring through early fall is often recommended for outdoor activities, cultural events, and comfortable temperatures around 54–85°F (12–30°C). Winter appeals to visitors who enjoy quieter streets and festive traditions.

  • What are the best places to visit in Greencastle?

    Explore the historic downtown, visit the campus of DePauw University, and enjoy natural surroundings at nearby parks. Locally rooted galleries and cultural spaces add to Greencastle’s appeal.

  • What are some hiking trails in Greencastle?

    Greencastle has walking and hiking trails in local parks, with scenic paths around wooded areas and community gardens. Nature preserves nearby give opportunities for longer hikes amid Indiana’s landscape.

  • What are some family activities we can do in Greencastle?

    Families can enjoy playgrounds and green spaces in local parks, educational events at community centers, and interactive exhibits at museums on the DePauw University campus. Outdoor picnics and seasonal festivals invite visitors of all ages.

  • What are some of the best day trip ideas from Greencastle?

    Explore local nature preserves, visit art museums in nearby towns, or experience regional festivals in surrounding communities. Outdoor enthusiasts often head to conservation areas for hiking or birdwatching.

  • Are there any pet friendly accommodations available in Greencastle?

    Greencastle has a variety of vacation rentals and accommodations that welcome pets, particularly in residential areas near local parks. Hosts often share guidelines about bringing pets, so it is helpful to check for pet policies before booking.

  • What are some local tips for visiting Greencastle?

    Bring layers for changing weather, and plan on walks through downtown to discover murals, locally owned shops, and cafés. Attending campus or community events is often recommended for meeting locals and experiencing Greencastle’s vibe.

  • What is Greencastle known for?

    Greencastle is known for its historic downtown, the vibrant campus of DePauw University, and locally rooted arts and music scenes. Community traditions and green spaces are also part of its distinct character.

  • What are the best hidden gems to explore in Greencastle?

    Artists’ murals around downtown, quiet walking trails, and community-run galleries showcase Greencastle’s creative spirit. Small cafés and historic homes often offer unexpected charm.

  • What are the best foods to try in Greencastle?

    Greencastle has locally rooted flavors, including classic Midwestern comfort foods, diner breakfasts, and seasonal pies made with Indiana produce. Barbecue and homemade ice cream are also frequently suggested.

  • What should I bring for a trip to Greencastle?

    Pack layers for variable temperatures, rain gear for spring and fall, and comfortable walking shoes for exploring parks and downtown streets. A reusable water bottle and a camera can also be useful for outings.

  • What is the nightlife in Greencastle like?

    Greencastle’s nightlife features laid-back venues with live music, campus events, and casual gathering spots. Downtown pubs and coffeehouses draw a mix of locals and visitors for evening conversation and entertainment.

  • What are the most popular events or festivals in Greencastle?

    Greencastle hosts community festivals in summer and fall, as well as arts and music happenings linked to DePauw University. Town fairs and seasonal celebrations are often recommended for visitors looking to connect with local traditions.

  • Are there family friendly vacation rentals in Greencastle?

    Family friendly vacation rentals in Greencastle are available in quiet neighborhoods, near parks, and within easy reach of community centers. Some hosts provide amenities like games and crib options for families traveling with young children.

Quick stats about holiday rentals in Greencastle

  • Total holiday rentals

    Explore 40 holiday rentals in Greencastle

  • Nightly prices starting at

    Greencastle holiday rentals start at $70 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,720 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Greencastle holiday 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!

  1. Airbnb
  2. United States
  3. Indiana
  4. Putnam County
  5. Greencastle