Holiday rentals in Winslow

Chestnut Street Retreat

A quaint and friendly neighborhood, with large backyard for kids playing, relaxing in the breeze way with morning coffee, or fun by the fire pit. Biking or walking around the neighborhood is safe and fun on a sunny day. Though you may feel in the country you are very close to downtown Huntingburg, 8 miles to Downtown Jasper. House is cozy and relaxing for a weekend away or if you're looking for activities Holiday World (18 Miles), Patoka Lake, French Lick Casino & West Baden Hotel (27 Miles).

Twin Lakes

Twin Lakes has a unique location on 60 acres in between 2 wildlife filled lakes stock with fish and wild geese flying in and out. A habitat for deer, squires and rabbits. The house is located down a long drive off the county road in a rural area. Very peaceful to sit on the back deck in the morning and enjoy a cup of coffee and watch the wildlife. Fishermen are invited to enjoy the lake from lakeside or small boat. The home is very comfortable with 2 queen size beds and a futon. Enjoy & relax!

Serenity Acres

Over 5 acres of pure serenity, just the sound of nature all around you! Beautiful Tucker Lake with hiking trail all around it just a mile away. This park like atmosphere has room for tents, RVs , boats, 4 wheelers and more. Just under 5 miles from the Fabulous French Lick and West Baden Resort town, but totally secluded.Cabin has two porches with rocker gliders and heavenly views. Cedar swing ,picnic table, fire pit with adirondack chairs for late night BBQs. Water park and boat rental, nearby

Lovely Country Loft Lake, Hiking, Woods, Relaxing

Take it easy at this unique and tranquil getaway. This loft was made from wood sawn and milled on this farm. Enjoy Indiana hardwoods as they surround you in this space. Centrally located, you are not far from Holiday World, Jasper, Lincoln City, Patoka Lake and Historic Huntingburg. The Master Bedroom boasts a king-size bed. The living area has two twin beds, TV, WiFi and Kitchen. This space is perfect for singles, couples, or small families. Most love the spiral staircase and large deck.

Whitetail Woods cabin w/ HOT TUB and Patoka pass

Relax with the whole family at this peaceful cabin minutes from Patoka Lake entrance, winery, distillery, brewery, and dining! Perfect for family adventures, romantic getaways, ladies' weekends, and hunting trips. The cabin is located in peaceful Grant Woods surrounded by gorgeous Southern Indiana nature. You'll love relaxing in the 6-person hot tub, rocking on the covered front porch, and roasting marshmallows around the backyard fire pit. Cabin is a short drive to French Lick/West Baden.

Riverfront Loft Above Honey Moon Coffee Shop

Located right on the riverfront in downtown Newburgh. Perfect access for walking, hiking, running, or bike riding on the popular riverfront trail. With epic views of the Ohio River including a 2nd story balcony view of beautiful sunrises and sunsets, our stylish loft apartment is located directly over Honey Moon Coffee shop. Please note that the loft is above a coffee shop that opens at 7am each day and you will hear some noise. 2 complimentary drip coffees are included with your stay!

The Getaway-3 Bed, 2 Bath, King Bed. Sleeps 6-10

3 Bedroom 2 Bath-Comfortably sleeps 7-10 people. King bed, Queen bed, PackNPlay, Fold Down Couch & Full Air Mattress downstairs. Two Twin XL beds, Daybed, 31x75 Cot & Futon upstairs. Whether you're looking to get away for a wedding weekend, off road riding & hiking at Interlake &/or Sugar Ridge SRA's, or fishing & kayaking at Lynnville Park, this is the perfect location to enjoy all this area of Southern IN has to offer. Easy access to I-64. Large pull through driveway for trailers.

The Bullpen Suite

Welcome to The Bullpen Suite, a newly remodeled apartment perfect for families and ball players. It features a kid-friendly loft, a cozy bedroom, a full kitchen, bathroom, and a theater-style living room. Enjoy exclusive access to Britton’s Bullpen Fort Branch, just 25 minutes from Deaconess Sports Park. Nearby, you’ll find KANT Brewery, R'z Cafe, Iron Horse Saloon, and Zac's Diner all within walking distance. The Bullpen Suite blends comfort, convenience, and local charm.

Peaceful Lake House Cabin 1, Direct Water Access!

This Cozy Cabin Duplex is located directly on West Boggs Lake, with a large, wrap-around, stationary dock to fish from, and multiple floating docks for your boat! Enjoy our kayaks, free with your stay, and explore all West Boggs has to offer! Cabin features 2 bedrooms with 2 Queen beds and a pull out sofa bed in the living room. Fully equipped kitchen, full bathroom, and an amazing deck for watching the sun set.

Country Escape 2

3 bedroom, 2 bathroom pole barn home with shared indoor game room. Spacious living area, bar seating and table for dining with full kitchen. Large game room includes pool table, ping pong, putting green and large tv with couch. Would make a great rental for contractors or a small family. This unit could be rented separately or in addition to the other large family home on the property.

Patoka River Hideaway

Take it easy at this cabin in the woods! If you are looking for a peaceful getaway nestled in the woods, you have found it! Located between Paoli and English this cabin sits back in the woods where you can see and hear the Patoka River flowing through. Sit out on the deck and enjoy our hot tub or firepit and relax! Enjoy your stay as a couple or small group to unplug and reconnect.

The Cabin - Near Holiday World & Splashin' Safari

If you'd like a true log cabin feel while staying on a beautiful, serene wooded 10 acre plot of land, this is the place for you and your friends/family! This small cabin has been reconstructed after being transferred to this location by the owner and his son. All of the decor and fixings are antique in style to fit the log cabin feel, to bring you back to the good ole days.