Holiday rentals in Greencastle

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Top-rated holiday rentals in Greencastle

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

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Guest favourite
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
4.96 out of 5 average rating, 217 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, 102 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
The exterior of a charming house is depicted, featuring light-colored siding and multiple gabled roofs. A landscaped path lined with flower pots leads to the entrance, surrounded by lush green grass and vibrant shrubs, creating a welcoming appearance in the daylight.
Home in Greencastle
4.96 out of 5 average rating, 55 reviews

Major Dunbar Home

Located directly off the DePauw campus, in the highly-coveted Eastern Enlargement Historic District, the attention to detail and premium amenities at Major Dunbar House will knock your socks off!! Enjoy our gourmet kitchen, 1st floor Master Suite, 3-spacious upstairs bedrooms, and 2.5 bathrooms. Our house can comfortably sleep 9 guests (with 5 individual beds, total). We are proud to serve the Greencastle and DePauw communities and we frequently welcome wedding-party guests from nearby venues.

Top guest favourite
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, 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
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, 134 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.

Guest favourite
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, 73 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 favourite
A charming one-room cabin features a wooden exterior with a green metal roof. Two blue chairs are placed on the small porch beside a door, which invites guests to enjoy the surrounding greenery in a tranquil setting.
Cabin in Bainbridge
4.94 out of 5 average rating, 110 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 favourite
Guest house in Greencastle
5 out of 5 average rating, 42 reviews

The Pond House at Deer Creek Farms/ Greencastle

10-min. to DePauw & downtown Greencastle is an idyllic 1 bdrm/1 ba cottage facing a stocked pond, woods & farm fields. King in bedroom, queen sleeper sofa in living room for extra guests. WiFi, TV, dining table/chairs, electric fireplace, kitchenette w/small fridge, coffee maker & microwave. Enjoy the grassy lawn, fire pit, fishing in pond, drinks on dock with Adirondack chairs and more. Families w/ young children please contact us before reserving to learn of safety concerns.

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, 205 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.

Top guest favourite
A charming two-story house is depicted, featuring light grey siding and a welcoming front porch. The well-maintained garden displays vibrant flowers and lush green grass. Concrete steps lead to the entrance, framed by soft greenery. The cloudy sky adds a serene backdrop to the scene.
Home in Greencastle
5 out of 5 average rating, 13 reviews

Haven on Hanna

Welcome to Haven on Hanna — your home base for campus visits, alumni weekends, or quiet getaways in the heart of Greencastle. Just steps from DePauw University and downtown, this spacious 3-bedroom, 4-bath home blends historic character with sleek, modern finishes. Sip coffee on the back patio, stroll to events at DePauw, and experience the best of small-town comfort with big hospitality.

Top guest favourite
A two-story house with a sloped roof and front porch is framed by symmetrical bushes on either side. A sidewalk leads up to the porch, which features steps and a railing. Grass lines the front yard, and a street sign stands nearby.
Home in Greencastle
4.96 out of 5 average rating, 26 reviews

Campus Cottage

Enjoy all the comforts of home in this charming, centrally-located house. Just one block from DePauw University and near downtown Greencastle, it features three bedrooms (1 king, 1 queen, and 1 twin bed), three full bathrooms, a fully equipped kitchen, and a delightful front porch. (1 queen size air mattress is also available)

Top guest favourite
A compact kitchenette is visible, featuring a stainless-steel refrigerator and microwave positioned above a counter with a coffee maker. Soft lighting from a lamp illuminates the nearby bedroom area, where a bed is dressed in neutral linens, enhancing the calming ambiance.
Flat in Greencastle
4.99 out of 5 average rating, 398 reviews

Charming apartment on the edge of DePauw campus.

After traveling around the world ourselves we know what its like to have a peaceful place to land and unwind. This apartment was designed with that in mind. We have been hosted by some of the finest people around the world and we desire to return the favor to those traveling through our lovely hometown.

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 £38 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 & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 of Greencastle holiday rentals include wifi 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