Holiday houses in Greencastle
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Top-rated holiday rentals in Greencastle
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“Lemon Blossom”Lakehouse by Brownsmith Studios
This home is a dream come true for me building it from the ground up. Bring your boat. No Partiers this home is being offered to families and couples who won’t disturb my neighbors or our peaceful cove. The home features a steam shower, king bed, reclining sofa, dock, kayaks,reading/social nook at signature windows over the creek/lake. The deck floats in the forest with abundant wildlife all around. premium WiFi . 15min to Bloomington. 20min to Nashville/Brown County St. Park. Newly paved lane
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.
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
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.
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.
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.
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.
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.
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.
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.
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.
Loft 202 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 one bedroom with a connecting bathroom, full kitchen, washer & dryer, key FOB entry, front door bell with camera, motorized shades, Wifi, & high end finishes that make this space feel unique and inviting.
Popular amenities for Greencastle holiday rentals
Other great holiday rentals in Greencastle
Overnight on Main
Raccoon Lake Retreat
Charming Retreat Near DePauw & Indy Hotspots
Depauw Dream Escape
Park Place
Modern 3BR Home Minutes from Campus & Restaurants
Cabin retreat
The Tiger's Den
When is the best time to visit Greencastle?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $318 NZD | $285 NZD | $295 NZD | $306 NZD | $337 NZD | $320 NZD | $276 NZD | $295 NZD | $318 NZD | $315 NZD | $313 NZD | $280 NZD |
| Avg. temp | -2°C | 0°C | 6°C | 12°C | 18°C | 23°C | 24°C | 24°C | 20°C | 13°C | 6°C | 1°C |
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 $84 NZD 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!
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- Lucas Oil Stadium
- Indianapolis Motor Speedway
- Indiana Convention Center
- Indianapolis Zoo
- Brown County State Park
- Eagle Creek Park
- The Golf Club at Eagle Pointe
- Gainbridge Fieldhouse
- Indiana State Fairgrounds & Event Center
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- Childrens Museum
- McCormick's Creek State Park
- Grand Park Sports Campus
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- Indiana State Museum
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