Holiday houses in Greencastle

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Greencastle

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

0 of 0 items showing

1 of 3 pages

Superhost

Cabin in Greencastle

4.81 out of 5 average rating, 70 reviews

Raccoon Lake Cabin

Relax with the whole family at this peaceful place to stay. This beautiful cabin sleeps four people comfortably. Galley kitchen, screened back porch, new rear deck with gas grill. Fire pit overlooking Lake. Lake access and boat dock available. This cabin has fiber optic Internet, 70 inch TV with surround sound, stereo system, fully stocked kitchen and a magnificent view of raccoon Lake. Owner also has five kayaks that can be a rented for an additional charge. This cabin sets in the woods.

Guest favourite

Loft in Greencastle

4.96 out of 5 average rating, 192 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.

Guest favourite

Barn in Greencastle

4.89 out of 5 average rating, 47 reviews

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

Top Guest favourite

Home in Greencastle

4.98 out of 5 average rating, 111 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.

Top Guest favourite

Home in Gosport

4.98 out of 5 average rating, 120 reviews

Maria’s Haven

Welcome to “Maria’s Haven”💕 A beautiful cozy home in the heart of a beautiful small town. This home belonged to my mother, Maria, who passed away in 2020 to breast cancer. This home was truly her “Haven”. Take a walk to the local diner, museum, Gosport playground, local shops, or to our delicious Amish bakery. We are also just a few miles from the popular “Hilltop” restaurant as well as McCormicks Creek State Park. Our mission is to make you feel like you never even left home. ☺️

Top Guest favourite

Loft in Greencastle

5 out of 5 average rating, 65 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.

Guest favourite

Home in Poland

4.96 out of 5 average rating, 204 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.

Guest favourite

Home in Greencastle

5 out of 5 average rating, 10 reviews

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.

Guest favourite

Home in Brazil

4.92 out of 5 average rating, 325 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 favourite

Cabin in Carbon

4.98 out of 5 average rating, 202 reviews

Parke County Dream Cabin

Come experience the serenity of country living and get away from the daily grind of everyday life. Come fish in our five-acre lake (catch & release only), paddle-boat, kayak, or stroll through the woods. A covered porch and seating lakeside for relaxing. Located close to Mansfield and Bridgeton, 30 minutes from Turkey Run State Park, and only 30 minutes toTerre Haute or Greencastle. Come explore everything Parke County has to offer! KIDS WELCOME!

Top Guest favourite

Loft in Greencastle

5 out of 5 average rating, 25 reviews

The Historic Boulders Circa 1910

Within walking distance to DePauw University and Downtown Greencastle in a park like setting on the historic Boulders property. Second floor private studio with an upscale kitchen with full set of appliances, queen size bed with power motion base, private bath, designated office area, WIFI, streaming video, 75 inch flat screen TV, central heat and AC, with access to outdoor patio and dining area with gas grill grill. Off street private parking

Top Guest favourite

Home in Greencastle

4.98 out of 5 average rating, 186 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.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodation and amenities

Popular amenities for Greencastle holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Greencastle

Superhost

Home in Greencastle

4.89 out of 5 average rating, 36 reviews

Splendor On Seminary

KristinaRating, 5 stars7 months ago

Another wonderful stay! Close to campus, comfy beds, full kitchen for cooking and lovely neighborhood. Pups were happy too. Thanks Josie for being a great host! :)

Guest favourite

Guesthouse in Rockville

5 out of 5 average rating, 10 reviews

Raccoon Lake Retreat

TimothyRating, 5 stars2 months ago

Place was absolutely gorgeous, the pallet wood wall in the living room with the different color stains was remarkable. Great parking for multiple vehicles and my large cargo trailer. Very quiet and peace and relaxing.

Guest favourite

Home in Greencastle

4.88 out of 5 average rating, 8 reviews

Quaint Home wlk to Town & DePauw

LewisRating, 5 stars3 weeks ago

Christina's cottage is a great place to stay if you need to be in the Greencastle area. It's very clean and well appointed and in a quiet neighborhood that is close to downtown.

Barn in Rockville

4.77 out of 5 average rating, 113 reviews

The 1938 Barn

EhlayRating, 5 stars2 weeks ago

The 1938 Barn was a wonderfully secluded peaceful getaway. The barn is full of charm and the bedroom apartment is comfy and clean. Brianna has done a great job renovating the old barn into a lovely stay. We had a fun time playing pool, enjoying the views, and being offline for a short while.

Top Guest favourite

Home in Greencastle

4.91 out of 5 average rating, 101 reviews

Martinsville Home

CharityRating, 5 stars3 weeks ago

We had a great stay at Larry’s place. We were visiting our son who coaches at DePauw and we needed something close to him. The house was super clean and had everything we needed.

Top Guest favourite

Loft in Greencastle

4.91 out of 5 average rating, 138 reviews

Courthouse Square Loft

HeidiRating, 5 stars1 month ago

Mackenzie's place was everything we hoped it would be. It was charming, very clean (most important feature), well-organized for guests, and a perfect location for walks to restaurants on the square in Greencastle and Depauw University. In the past, we have always stayed at the Inn at Depauw when visiting Greencastle. We will always seek to stay at Mackenzie's place from now on. We are so very grateful to have such a lovely space to access for short visits when we are in the area. Thank you, thank you, thank you! Heidi

Guest favourite

Cabin in Monrovia

4.97 out of 5 average rating, 91 reviews

Waterfront getaway *cozy & peaceful*fishing*swings

JaydenRating, 5 stars1 week ago

Wonderful little lot that was very secluded and private while still being a reasonable driving distance to activities. Pier and fire pit offer serene natural environment with many ambient sounds and wildlife to watch and listen to. The house is perfectly small to comfortable fit two with all of the amenities needed to find yourself at home.