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Vacation rentals in Greencastle

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Greencastle

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A spacious modern structure is set against a clear blue sky, featuring a hip roof and large windows that allow natural light to fill the interior. The exterior is accented by stone pillars and a wide porch, surrounded by a grassy field.
Home in Greencastle
5 out of 5 average rating, 54 reviews

Quiet Country Retreat Near DePauw University

Discover the charm of Throttle Back Ranch, a brand-new (2023) home just minutes from Greencastle, DePauw University, Cataract Falls State Park, Putnam Park Road Course, and Cowpokes Arena. Racing enthusiasts will love our unique touch - a full-size race car mounted on the wall! Enjoy country living at its best, with a fully equipped kitchen, entertainment options, and an expansive covered porch for breathtaking sunset views. Feel free to reach out with questions. We can't wait to host you!

Guest favorite
The exterior of Namaste Lofts is shown, highlighting the red brick faƧade and large windows with green awnings. Nearby sidewalk seating is visible, along with surrounding storefronts, creating a vibrant downtown atmosphere.
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 favorite
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, 100 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 favorite
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
4.92 out of 5 average rating, 155 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 favorite
Cabin in Unionville
5 out of 5 average rating, 203 reviews

Summer Escape: 40 Acre Forest Spa Trails & Boating

Summer Forest Reset🌳🐿 Rejuvenate in 2 bedrooms featuring king-sized beds šŸ–ā˜•ļø BBQ shed & Coffee bar šŸ”„šŸ›€ 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 favorite
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.
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
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.
Home in Greencastle
4.89 out of 5 average rating, 111 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.

Top guest favorite
A modern living area is showcased with high ceilings and large windows allowing ample natural light. A sleek gray sofa complements a dark coffee table and is paired with minimalist seating options. A mounted TV is positioned above a low console, and artwork adorns the wall.
Loft in Greencastle
5 out of 5 average rating, 72 reviews

Loft 201 on Greencastle square above Bridges

Thank you for your interest in our contemporary loft on the Greencastle square above Bridges Craft Pizza & Wine bar. This apartment features 2 bedrooms, one being a loft on the second floor with a connecting bathroom. The second bedroom is on the main floor with a bathroom across the hall. This apartment also includes a full kitchen, washer & dryer, FOB key entry, front door bell with camera, motorized shades, WiFi, & high end finishes that make this place feel like a one of a kind.

Top guest favorite
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
4.93 out of 5 average rating, 107 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.

Guest favorite
A serene pool area is framed by lush greenery, highlighted by a sparkling pool with colorful floats. Cozy lounge chairs provide inviting seating around the pool, complemented by shaded gazebo spaces, ideal for relaxation. The scene reflects a tranquil outdoor retreat.
Home in Poland
4.94 out of 5 average rating, 230 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.

Top guest favorite
A single-story home is displayed, featuring a light-colored exterior with a red metal roof. A spacious porch, equipped with seating, is visible at the front. Surrounding grass is neatly maintained, and trees provide natural shade nearby.
Home in Brazil
4.93 out of 5 average rating, 370 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 favorite
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, 203 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

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 cafĆ©s. 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 cafĆ©s 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 vacation rentals in Greencastle

  • Total vacation rentals

    Explore 40 vacation rentals in Greencastle

  • Nightly prices starting at

    Greencastle vacation rentals start at € 43 per night before taxes and fees

  • Verified guest reviews

    Over 2,720 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 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!

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