Vacation rentals in Fillmore

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Top-rated vacation rentals in Fillmore

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

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Top guest favorite

A dining area features a round wooden table surrounded by transparent chairs, complemented by plush white seat covers. A modern chandelier hangs from the ceiling, illuminating the space. The room showcases a combination of hardwood flooring and black accent walls, with large sliding glass doors leading outdoors.

Home in Greencastle

4.98 out of 5 average rating, 110 reviews

Modern 4 Bed Home On Golf Course Close To Campus +

4 bedroom, 2 bath-master w/shower guest ba w/tub & shower ranch home w/ 5th hole of the golf course as your view & literally steps from patio! Minutes from campus, restaurants & shopping. Quiet established neighborhood. (1) King bdrm, (2) bdrms w/full bed and (1) office/bedroom w/fold down couch. -Blackout curtains -Wifi -Spacious family room w/smart 75 in TV -Close to everything Outdoor patio w/furniture to enjoy the golf course views. Depauw themed basement w/ sauna, pool & poker tables

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Top guest favorite

A shaded porch area is visible, featuring several turquoise chairs arranged closely together along a concrete path. Lush greenery and blooming flowers frame the scene, offering a serene outdoor space conducive to relaxation.

Barn in Greencastle

4.93 out of 5 average rating, 69 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

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Guest favorite

The exterior of the A-frame cabin is framed by lush greenery, showcasing a wooden deck with potted plants at the entrance. The black exterior features large windows, allowing natural light to brighten the interior spaces. Gravel pathways lead to the cabin amidst the tranquil wooded surroundings.

Cabin in Rockville

4.99 out of 5 average rating, 106 reviews

Walker Getaway | A-Frame•Hot Tub•Decks•Lake•Hiking

Escape to Walker Getaway, an updated A-frame cabin on 5 private wooded acres w a creek, hot tub, fire pit and multi-level decks. Located across from Walker Boat Ramp and only 5 minutes from Raccoon Lake Beach. Use the provided Indiana State Park pass to explore nearby Turkey Run and Shades. Fully stocked and family-friendly, it’s perfect for couples, friends, or families looking to relax, recharge, and explore Parke County. Walker Getaway is where modern comfort meets Indiana’s natural beauty.

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Top guest favorite

The exterior of a charming house is depicted, featuring light-colored siding and multiple gabled roofs. A landscaped path lined with flower pots leads to the entrance, surrounded by lush green grass and vibrant shrubs, creating a welcoming appearance in the daylight.

Home in Greencastle

4.97 out of 5 average rating, 58 reviews

Major Dunbar Home

Located directly off the DePauw campus, in the highly-coveted Eastern Enlargement Historic District, the attention to detail and premium amenities at Major Dunbar House will knock your socks off!! Enjoy our gourmet kitchen, 1st floor Master Suite, 3-spacious upstairs bedrooms, and 2.5 bathrooms. Our house can comfortably sleep 9 guests (with 5 individual beds, total). We are proud to serve the Greencastle and DePauw communities and we frequently welcome wedding-party guests from nearby venues.

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Top guest favorite

A charming one-room cabin features a wooden exterior with a green metal roof. Two blue chairs are placed on the small porch beside a door, which invites guests to enjoy the surrounding greenery in a tranquil setting.

Cabin in Bainbridge

4.94 out of 5 average rating, 118 reviews

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, or find inspiration. With raw poplar walls, the cabin offers a full-sized bed by a picture window, small TV, writer's desk/library, air conditioning, 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.

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Top guest favorite

A cozy bedroom features a dark wood bed with clean linens and two pillows. A lamp sits on a nightstand beside the bed. A window with dark curtains allows natural light to filter in, and framed art is displayed on the wall.

Home in Greencastle

4.98 out of 5 average rating, 140 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.

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Top guest favorite

Cabin in Unionville

5.0 out of 5 average rating, 220 reviews

Elevated Wilderness | Mindful Retreat | 2 Kings

Executive Forest Sanctuary/2 King Beds, Hot Tub & Trails Escape to an architectural masterpiece set on 40 wooded acres. Designed for professionals, couples, and active adults seeking a high-end nature reset, Cabin Porch Paradise balances 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 ridge top retreat.

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Top guest favorite

A historic farmhouse with a large wrap-around screened-in porch is set against a backdrop of autumn leaves. A gravel pathway leads to the main entrance, and several white Adirondack chairs are positioned on the lawn, inviting guests to relax and enjoy the surroundings.

Home in Greencastle

5.0 out of 5 average rating, 38 reviews

Authentic Family Farmhouse on Pond / Greencastle

Family Farmhouse surrounded by woods & crop fields, an expansive lawn, pond, screened-in porch, fire pit and historic barn. 10 min. to downtown Greencastle & DePauw/35 min. to IND airport. Ideal for a multi-generational family or friends gathering for special events.Adjacent guesthouse can be reserved to sleep 4 more. Fishing poles, yard & board games provided. Children are welcome, but please send inquiry to hosts about safety concerns for little ones before reserving.

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Top guest favorite

A lakefront house in warm golden tones is depicted among tall, leafy trees. The property features a two-car garage, a gravel driveway, and a prominent walkway leading to the entrance, with scenic views of the lake visible in the background.

Cabin in Rockville

4.99 out of 5 average rating, 102 reviews

Classic Lakefront Retreat on Raccoon Lake

Your dream lakefront retreat on Raccoon Lake awaits! This 3,800 sqft lake house is screaming with character - exposed timber beams and serene views are just the beginning of what this mid-century vacation home has to offer. Enjoy traditional charm combined with modern amenities and conveniences like 1Gb fiber internet. This vacation home is lakefront, with private access to a private dock where guests can dock a boat. Parties not permitted. Registered guests only.

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Guest favorite

A spacious heated pool is surrounded by lounge chairs and umbrellas, set in a lush garden area. The inviting pool features a fountain, while the deck offers ample seating for relaxation. A cozy living space features comfortable seating, a flat-screen TV, and a dining table amid warm wood accents.

Home in Poland

4.94 out of 5 average rating, 140 reviews

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.

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Top guest favorite

The home features a charming facade with a gabled roof and symmetrical design. Two American flags are displayed on the front. A well-maintained lawn surrounds the house, complemented by neatly trimmed shrubs. A inviting walkway leads to the entrance, flanked by wooden chairs.

Home in Greencastle

4.99 out of 5 average rating, 210 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.

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Guest favorite

A charming two-story house is depicted, featuring light grey siding and a welcoming front porch. The well-maintained garden displays vibrant flowers and lush green grass. Concrete steps lead to the entrance, framed by soft greenery. The cloudy sky adds a serene backdrop to the scene.

Home in Greencastle

5.0 out of 5 average rating, 17 reviews

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.

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