Holiday rentals in Greentown

The 1889

A historic treasure gently awakened for the modern traveler. From its grand staircase to its cozy nooks, this 1889 home has been fully reimagined—offering peace, warmth, and classic Midwestern hospitality Enjoy a meticulously updated interior for up to six guests, premium finishes, and cozy spaces just minutes from local favorites. Come be a part of the story and book today! 5 minutes from Kokomo Speedway, 10 minutes from Championship Pk 40 minutes to Grand Pk, 1 hr to Indiana Beach 1 hr 20✈️

Cozy Country Bear log cabin with many amenities

You won’t forget the peaceful surroundings of this rustic destination. Enjoy wildlife, kayaking, fishing, campfires, horses, hiking and games. We also have a sauna and a hot tub available on the premises There is Roku TV and WIFI in the cabin. You can sit on the front porch and enjoy the swing or rocking chairs and listen to the night sounds or chat with friends. You can also enjoy a campfire and cook over the open fire on our tripod grill. We have 2 other cabins and our cozy apartment listed.

Sunlit Sanctuary w/Country View. Tranquil & Clean.

Retreat to the country with this newly renovated guest house. Located just 8 minutes away, this modern space offers a tranquil, country setting with quick, easy access to Kokomo. A lovely space to unwind and relax after a busy day at work or play, this quiet setting ensures you rest peacefully. In the morning, after drawing back the blackout curtains, take in the serene views of the countryside and perhaps catch a glance of the local wildlife as rabbits, squirrels and birds are abundant.

Vintage Farmhouse Charm

Welcome to Grace Farm, this house and farm have been part of our family for over 100 years. It is newly renovated to reflect our rural farm heritage. The house is spacious and ready to host your family gathering, girls weekend or peaceful retreat. Explore the barns, hay field, fire pit; ride bikes or walk along the quiet country road and find the beaver dams in the creek. Our farm is 20 minutes from Indiana Wesleyan, 30 minutes from Taylor University and 1 hour to Indy and Fort Wayne.

The Brick-Road Penthouse - 5BR, 4BATH, Walkable

Stay in the entire top floor of Kokomo’s most iconic Building. This stunning 5BR/4BA penthouse blends historic charm with modern design—featuring a grand piano, glass fireplace, and open-concept living. Walk to top restaurants, breweries, festivals, and the Heritage Trail. Ideal for business, groups, retreats, or unforgettable getaways. Privacy, style, and location all in one. ✔️ Entire 3rd Floor ✔️Walkable Location Downtown ✔️ Wifi ✔️Smart TV's ✔️Full Kitchen & Laundry ✔️Free parking

Parkside Perch - King Bed - large covered balcany

✩ Parkside Perch Highlights ✩ • Newly renovated Living Space • 110 sq ft covered balcony • Walking distance for all interests • Dream Coffee Bar for any style. • Park across the street offers pickleball, basketball, tennis, large playground, and live music featured on weekends. • Access Kokomo's paved trail across the street and walk or bike for miles. This space is perfect for small families, traveling professionals, or anyone looking to spend some time in downtown Kokomo.

The Cozy Corner

Kick back and relax in this calm, stylish space, which has just been completely renovated! New white spaces with lots of comfy touches will be sure to relax your mind and rejuvenate your soul! Come get away and relax or connect with family/friends. Play games in the living room with friends or sit around the firepit area outside to enjoy smores and conversation. This home is conveniently located in a rural area 5 minutes from Greentown and 7 minutes from Kokomo.

1890's Farmhouse

Welcome to our mid-century modern farmhouse retreat! This stylish and spacious home features four bedrooms & two bathrooms, making it perfect for couples, families, or groups of friends looking for a place to call a temporary home, just 35min north of Indy. This home is cozy with mid-century furnishings and decor throughout. Each bedroom is simple yet tastefully decorated & the overall space is clean and cozy for guests to have a memorable experience.

The Garden Cottage at The English Rose

The Garden Cottage at The English Rose is a beautiful, clean, spacious, light and airy 750 sqft , 1 bedroom, 1 bath apartment. This renovated carriage house is adjacent to our 1903 Queen Anne Victorian and is a registered historical landmark of Kokomo, Indiana. The garden cottage gets it’s name by being surrounded by beautiful lush perennial gardens. Only registered guests allowed. Small, well trained, apartment dogs under 12lbs allowed.

Grandma’sFarmhouseonNickleplate

Walk into the door of a old country farmhouse it feels kinda like grandmas. With warm touches, antiques and a unique twist of modern along with old floors, sweet treats and quilts. It is comforting to sit by a modern fireplace and a relaxing countryside. A big desk space in the kitchen if you need a workspace. Come and sit down and take the pressure off of life kicking back at this Grandma’s farmhouse special.

Sweet Escape

Welcome to your cozy retreat near Highland Park! This charming, fully furnished home offers the perfect blend of updated comfort and nostalgic charm. Nestled in a peaceful neighborhood, it’s the ideal escape with everything you need just a few miles away—whether it’s grocery stores, dining, or shopping. Experience warmth and comfort in every corner of this inviting space, designed to make you feel right at home.

Adorable Dutch Colonial Home

Bright and cheerful with a modern twist. This beautifully remodeled home has all the amenities that are needed to make your stay enjoyable. Take advantage of the 3 season room and watch the squirrels play in the backyard or take a stroll to the walking path for some fresh air and a riverfront view. Just minutes from downtown shopping and many restaurants to make your stay enjoyable.