Greencastle Vacations from $540

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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.
Hotel Nashville

Hotel Nashville

$540
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Indianapolis (IND)
8.4/10 Very Good! (958 reviews)
 Spacious 5-Bedroom Blue Bungalow

Spacious 5-Bedroom Blue Bungalow

$857
per person
Sep 23 - Sep 27
found 8 hours ago
Roundtrip non-stop flight included
New York (LGA) to Indianapolis (IND)
No reviews
Hilton Garden Inn Bloomington

Hilton Garden Inn Bloomington

Downtown Bloomington
$1,003
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Indianapolis (IND)
8.6/10 Excellent! (1,008 reviews)
This is the location for experiencing the best of Bloomington

Reviewed on Aug 13, 2026

Spacious Duplex for 14 in Downtown

Spacious Duplex for 14 in Downtown

$858
per person
Sep 23 - Sep 27
found 8 hours ago
Roundtrip non-stop flight included
New York (LGA) to Indianapolis (IND)
No reviews
Cozy 3BR Home in Bates-Hendricks

Cozy 3BR Home in Bates-Hendricks

$597
per person
Sep 23 - Sep 27
found 8 hours ago
Roundtrip non-stop flight included
New York (LGA) to Indianapolis (IND)
No reviews
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Stay near popular Greencastle attractions

Skeins of yarn in various colors hanging in a store.
Photo by Sig

Putnam County Fairgrounds

8.2/10 (31 reviews)
The Putnam County Fairgrounds hosts Indiana's cherished agricultural showcase featuring livestock exhibitions, community events, local culture, and traditional competitions each July, complete with regional food vendors.
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A cluster of white flowers growing from a tree stump in a forest.
Photo by Sig

Jaycee Park

Explore the great outdoors at Jaycee Park, a lovely green space in Greencastle. Take in the festivals while you're in the area.
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DePauw University

9.2/10 (52 reviews)
DePauw University's historic campus blends classic architecture with vibrant student life in Greencastle. Visitors can enjoy public lectures, art exhibitions, and performances that showcase its academic excellence.
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Lincoln Park Speedway

8.8/10 (17 reviews)
This classic 5/16-mile dirt oval delivers electrifying Saturday night racing with sprint cars, modifieds, and more. Arrive early to claim prime grandstand spots or bring lawn chairs for the grassy viewing areas.
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DePauw Nature Park

8.6/10 (48 reviews)
This former limestone quarry transformed into a 520-acre natural sanctuary offers over 10 miles of diverse trails. Explore the unique geological features and scenic vistas along the Quarry and Rim Trails.
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Micaela Cancilla Park

Micaela Cancilla Park is just one of the places to see in Greencastle, so why not enjoy the other things to explore during your travels? Take in the festivals while you're in the area.
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Blackstock Stadium

Catch an event at Blackstock Stadium during your trip to Greencastle. Take in the festivals while you're in the area.
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Judson and Joyce Green Center for the Performing Arts

Enjoy an outing to Judson and Joyce Green Center for the Performing Arts during your stay in Greencastle. Take in the festivals while you're in the area.
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Greencastle Hotel Deals

Inn at DePauw

Inn at DePauw

2 West Seminary Street Greencastle IN
Fully refundableReserve now, pay when you stay
$160 nightly
$179 total
Aug 23 - Aug 24
Total with taxes and fees
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 IN
$230 nightly
$258 total
Aug 16 - Aug 17
Total with taxes and fees
9.6/10 Exceptional! (59 reviews)
"The home was nice and the grounds were beautiful. We needed to add a day on the front end last minute and the host was very accommodating. There were 5 of us but they had plenty of bedding and sheets and so we all had somewhere comfortable to sleep regardless of it being a 2 bedroom. It is close ..."

Reviewed on Aug 5, 2026

2-bedroom vacation home minutes away from Greencastle and Depauw campus
Secluded Cabin in the Woods, Private Nature Retreat Near Greencastle & I-70

Secluded Cabin in the Woods, Private Nature Retreat Near Greencastle & I-70

Greencastle IN
Secluded Cabin in the Woods, Private Nature Retreat Near Greencastle & I-70
See all 187 properties in Greencastle
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.

Find the Best Greencastle Vacation Packages

Things to do in and around Greencastle

Greencastle, Indiana offers a delightful blend of outdoor adventures and scenic beauty, making it ideal for leisure travelers and romantic getaways. Visitors can explore magical waterfalls, enjoy recreational areas, and partake in arena entertainment. Whether you're looking for a quick tour or a relaxing beach vacation, Greencastle has activities that cater to all interests, ensuring a memorable experience for everyone.

Shopping

For a unique shopping experience, visit Traderbaker Flea Market, located 28 miles away from Greencastle. This lively public market offers a variety of goods and local vendors, providing a vibrant atmosphere perfect for finding gifts and souvenirs.

Recreation

Experience relaxation at Wabash Valley Family Sports Center, where wellness meets recreation 25 miles from Greencastle. Enjoy family fun at Crawfordsville Aquatic Center, a vibrant pool complex 26 miles away. For a sporty outing, visit Hulman Links Golf Course, also 26 miles from Greencastle, offering beautiful outdoor scenery.

Adventure

Explore DePauw Nature Park for an invigorating hiking experience through scenic trails, perfect for outdoor enthusiasts. For adrenaline junkies, Lincoln Park Speedway offers thrilling motor racing events, combining speed and excitement in an energetic atmosphere.

Nightlife

In Greencastle, enjoy a cozy nightlife scene with local bars and restaurants. Visit The Inn at DePauw for a lively atmosphere, or check out the local pubs for craft beers and live music. Stroll through downtown to find intimate spots perfect for a relaxed evening with friends.

*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 perfect for outdoor adventures and scenic experiences. Explore urban parks, historic colleges, and fairgrounds, making it ideal for family outings and city exploration. Be sure to check out popular attractions, as well as local golf motels for a relaxing stay. Whether you're looking for nature or history, Greencastle offers a variety of activities that cater to every traveler.

  • Putnam County Fairgrounds: Experience the lively atmosphere at Putnam County Fairgrounds, where family-friendly events and outdoor activities come to life. This fairground is perfect for enjoying local fairs, festivals, and community gatherings, offering a taste of small-town charm.
  • DePauw University: Immerse yourself in the rich history and culture of DePauw University. Stroll through its picturesque campus, admire the historic architecture, and engage with the vibrant arts scene that includes galleries and performances, reflecting the university's commitment to excellence.
  • Greencastle Dog Park: Enjoy a relaxing day at Greencastle Dog Park, a welcoming space for dogs and their owners. With open areas for play and socialization, it's an ideal spot to unwind, meet fellow dog lovers, and let your pup have some fun.

Best time to go to Greencastle

The best time to visit Greencastle is dependent 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 cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.4°F (-2.0°C)Light RainMostly CloudyAverageSlightly Low
February31.5°F (-0.3°C)Light RainMostly CloudyAverageAverage
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 RainMostly CloudySlightly LowSlightly Low

Tips to save on your trip to Greencastle

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Greencastle.
  • 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.

Greencastle Essential Information

Language
English
Currency
U.S dollars
Population
10,400
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
DePauw University, Lincoln Park Speedway and DePauw Nature Park

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Frequently asked questions

How much does a Greencastle vacation package cost?
You'll find cheap prices from $540 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.

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