Holiday houses in Fillmore

Elevated Wilderness | Mindful Retreat | 2 Kings

Executive Forest Sanctuary/2 King Beds, Hot Tub & Trails Escape to an architectural masterpiece set on 40 private, wooded acres. Designed for professionals, couples, and active adults seeking a high-end nature reset, Cabin Porch Paradise balances complete seclusion with proximity to Southern Indiana’s best destinations. Whether you are unwinding in the spa amenities, working remotely via high-speed fiber, or exploring the surrounding lakes and state parks, this is your ultimate ridgetop retreat.

Value · Family · Check-in

A little secret hideaway

Keep it simple at this peaceful and centrally-located place. It’s close to everything, making it easy to plan your visit. It’s close to the airport, sporting events, and downtown. It’s up on the second level, but separate from the downstairs living. It has its own entrance and living space. 2.3 miles to Indianapolis airport 5.1 miles to Lucas Oil IRP 5.3 miles to Indianapolis Motor Speedway 8.3 miles to Lucas Oil Stadium 8.8 miles to Gainbridge Fieldhouse 8.8 miles to Indianapolis Downtown

Family · Location · Bathroom

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

Family · Location · Checkout

Overnight on Main

Overnight on Main is the perfect stay if you are visiting the west side of Indiana. Here's what you'll have easy access to! - Indianapolis International Airport - 28 minutes east - Cataract Falls State Rec/ Park - 11 minutes south - DePaw University/ Greencastle - 15 minutes north - Lieber State Rec/ Park - 10 minutes southeast - C Bar C Expo Center - 2 miles north (4 min) You will also have easy access to local amenities and restaurants, some just a quick walk across or up the sidewalk!

Value · Family · Hospitality

Cozy Lofted Cabin (#1) at Cataract Lake Getaway

This new cabin on a private road is a serene setting perfectly blending rustic charm and modern comfort. Only a half-mile from Cataract Lake, quick and easy access to boating, fishing, kayaking, etc. awaits! Numerous nearby attractions are sure to provide great experiences (Cataract Falls, C Bar C Event Center, Exotic Feline Rescue Center, state parks, brewery/winery, local shops/eateries, etc.) And of course, simply enjoying time in and around the cabin itself is a fulfilling getaway!

Family · Value · Air conditioning

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.

Family · Location · Checkout

Woodlands at Countryside Estates

Escape to nature in this charming tiny glamping cabin nestled near Cagles Mill Lake. This peaceful retreat sits near the end of a private lane in Countyside Estates, surrounded by a rustic woodland setting, perfect for those seeking solitude, camping with modern conveniences or a quiet getaway. It’s located near the public boat launch for Cagles Mill Lake to enjoy many water sport activities. (1.9 miles) The cabin is also close to Lieber State Rec Area and Cataract Falls.

Location · Amenities · Bathroom

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!

Family · Value · Pool

Clean, functional and charming home

Clean and inviting home with an open floor plan and intimate spaces to relax and enjoy your time here. We are located just 7 minuets from DePauw University, 3 minutes from 3 Fat Labs and 12 minutes from Owl Ridge wedding venue. For those coming to enjoy events at C Bar C Expo Center, we are a short 21 minute drive, Lincoln Park Speedway 15 minutes, and for Indiana's premiere Bridge Festival, Mansfield is only 25 minuets away.

Value · Location · Quiet

Captain Bill’s Lake House Heated Salt Water Pool

Captain Bill’s Lake House. This majestic A-frame is at the entrance to the Cataract Lake boat ramp. The house will accommodate up to 7 guests, with three bedrooms and two full baths. All guests have full access to Captain Bill’s shared heated salt water pool and surrounding gardens. Boat parking is available on the property, inquire for details. Heated Salt Water Pool is seasonal beginning May 1, through September 30th.

Family · Value · Walkability

Rare Find. An Experience. Treetop Deck. Ravines.

A truly rare gem. Tucked into the trees, three sides surrounded by wooded ravines, this inviting retreat features a breathtaking treetop deck—perfect for relaxing, unwinding, and soaking in the beauty of nature. Secluded A-frame cabin situated on 2 private acres, bordering 2,700 acres of protected forest. Sleeps 6 with 2 bedrooms, sleeper sofa, memory foam beds, full kitchen, high-speed internet.

Family · Location · Checkout

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.

Family · Location · Accuracy