Greencastle Vacations from $266

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Your Greencastle Vacation

Skip the stress of planning your next epic adventure with a Greencastle vacation package. Whether you're in town for its cuisine, history, art or other highlights, there's a never-ending supply of new experiences to be had. Make your trip to Greencastle even more fun and exciting by including some sightseeing. DePauw University, Putnam County Fairgrounds and Lincoln Park Speedway are some of the big attractions worth exploring. Expedia is here to help you escape your daily routine. Tailor your vacation to Greencastle to suit your travel style, whatever that may be.

The Latest Greencastle vacation packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Indianapolis-N.E./Castleton
Embassy Suites by Hilton Indianapolis North
Bottleworks Hotel
Landing Apartments Indianapolis - Bayview
Holiday Inn Indianapolis Downtown by IHG
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Greencastle Hotel Deals

Inn at DePauw

Inn at DePauw

3.5 out of 5
2 West Seminary Street, Greencastle, IN
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $179 total per night from Aug 31 to Sep 1
$179 total
Aug 31 - Sep 1
Total with taxes and fees
9.2/10 Wonderful! (272 reviews)
"Fine hotel close to university and downtown."

Reviewed on Jul 30, 2025

Inn at DePauw
2-bedroom vacation home minutes away from Greencastle and Depauw campus

2-bedroom vacation home minutes away from Greencastle and Depauw campus

Greencastle
$230 nightly
The price is $258 total per night from Aug 31 to Sep 1
$258 total
Aug 31 - Sep 1
Total with taxes and fees
9.4/10 Exceptional! (28 reviews)
"Lovely comfortable home. Beautiful grounds. Peaceful with walking paths and beautiful trees. Exactly what we were looking for. Close to Depauw. Nice restaurants in nearby Greencastle. My host was gracious and responsive. Highly recommend When we return to this area next spring, we defitnitly check ..."

Reviewed on Aug 25, 2025

2-bedroom vacation home minutes away from Greencastle and Depauw campus
Charming Greencastle Home < 1 Mi to Depauw!

Charming Greencastle Home < 1 Mi to Depauw!

3 out of 5
Greencastle
Charming Greencastle Home < 1 Mi to Depauw!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Things to do in and around Greencastle

Greencastle, Indiana offers a delightful mix of outdoor adventures and scenic beauty, perfect for a memorable vacation. Explore local education centers, enjoy recreational areas, and visit the fairground for events. Ideal for romantic getaways and day trips, you can also discover magical waterfalls nearby. Whether you're after quick tours or beach vacations, Greencastle provides a charming backdrop for a relaxing escape.

Shopping

In Greencastle, you can check out local shops and boutiques for unique gifts. If you're up for a drive, visit Traderbaker Flea Market, located 28 miles away, where you can find a variety of items in a vibrant market atmosphere.

Recreation

The Wabash Valley Family Sports Center, 25 miles from Greencastle, provides a welcoming atmosphere for relaxation and fitness activities. The Crawfordsville Aquatic Center, 26 miles away, offers fun for the whole family with its pool and sports amenities. Enjoy a round of golf at Hulman Links Golf Course, also 26 miles from town.

Adventure

Experience the thrill of racing at Lincoln Park Speedway, where you can feel the rush of speed and adrenaline in a vibrant motorsport atmosphere. For a more tranquil adventure, explore the scenic trails of DePauw Nature Park, perfect for hiking amidst beautiful outdoor landscapes.

Nightlife

Greencastle offers a charming nightlife with cozy pubs and bars. Enjoy craft beers at The Putnam Inn or unwind at the Brick House Grill for delicious food and drinks. For live music and local talent, check out The Roost, a popular spot among locals and visitors alike.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Greencastle

Greencastle, Indiana, is an ideal destination for outdoor enthusiasts and families, offering a mix of urban parks, historic college surroundings, and fairgrounds. Visitors can enjoy exploring local attractions like the picturesque parks and engaging in city experiences. For those seeking leisure, there are opportunities for golfing and staying at motels. This charming town provides a perfect blend of adventure and relaxation for all travelers.

  • DePauw University: Immerse yourself in the rich culture and history of DePauw University, a historic institution known for its beautiful campus and vibrant arts scene. Attend a concert, art exhibit, or a sporting event to experience the lively atmosphere that surrounds this esteemed college.
  • Putnam County Fairgrounds: Enjoy a family-friendly atmosphere at the Putnam County Fairgrounds, where you can participate in various outdoor activities, fairs, and events throughout the year. It's a great place to experience local culture, food, and fun.
  • Greencastle Dog Park: Bring your furry friend to the Greencastle Dog Park, a well-maintained space where dogs can socialize and play. It's a perfect spot for pet owners to relax while their dogs enjoy some recreational time.

Best time to go to Greencastle

The best time to visit Greencastle is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.4°F (-2.0°C)Light RainMostlyAverageSlightly Low
February31.5°F (-0.3°C)Light RainMostlyAverageAverage
March42.6°F (5.9°C)Light RainMostly SunnySlightly HighAverage
April52.3°F (11.3°C)Light RainMostly SunnySlightly HighAverage
May63.1°F (17.3°C)Light RainMostly SunnyAverageSlightly High
June71.6°F (22.0°C)Light RainMostly SunnyAverageAverage
July74.3°F (23.5°C)Light RainMostly SunnyAverageAverage
August72.9°F (22.7°C)Light RainMostly SunnyAverageAverage
September67.3°F (19.6°C)Light RainMostly SunnySlightly HighSlightly High
October55.6°F (13.1°C)Light RainMostly SunnySlightly LowSlightly High
November43.0°F (6.1°C)Light RainMostly SunnySlightly LowSlightly Low
December34.7°F (1.5°C)Light RainMostlySlightly LowSlightly Low

Tips to save on your trip to Greencastle

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Greencastle during the low season (November to January) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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Frequently asked questions

How much does a Greencastle vacation package cost?
You'll find cheap prices from $266 on Expedia for your Greencastle getaway. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Greencastle costs.
What are the cheapest months to go to Greencastle?
If you'd like to book a cheap Greencastle vacation package, consider traveling in February, October and December. You're likely to find lower prices on hotels and airfares during these months — ideal for a budget-friendly break.
How many days is enough for Greencastle?
The ideal length for your Greencastle vacation depends on what you'd like to do. Usually, a few days to a week will give you enough time to tick off all the top sights and explore some hidden treasures along the way.
Is it worth booking a vacation package to Greencastle?
Popular for its walking trails, hiking and festivals, a Greencastle vacation is a hit with all types of travelers. Be sure to visit main sights like Putnam County Fairgrounds and DePauw Nature Park, and consider renting a car for day trips to experience even more.
How to find the best Greencastle package deals?
Begin your search for a Greencastle package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Greencastle package deal right away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Greencastle getaway off to a flying start.
Is it cheaper to book a Greencastle vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and stays separately. Better still, you can customize your Greencastle escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Greencastle?
Land amazing discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Greencastle adventure.
Does Expedia offer Book Now, Pay Later Greencastle vacation packages?
Your Greencastle break should be an escape from your daily routine, not a reason for money-related stress. So to allow you a bit more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.