Holiday houses 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).

Spacious 1450 sf 2 BR Private Suite Apartment

This Apartment style basement suite is a comfy space with 1450 sf of living space. Dogs are welcome and we will also share our back fenced dog park! The basement has a private entry, Sleeps 9, and was renovated in 2022. Our home is comfortable with modern & vintage decor. Each bedroom has a bed, closet, dresser, nightstand & desk. We are not a wheelchair friendly home. We are a dog paradise and all breeds welcome. Our third sleeping area is a non-enclosed area you walk through to bedrooms.

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!

10 min from Holiday World —Family Escape

This spacious 4 bedroom house is filled with coziness, games for kids (and adults) and plenty of space to spread out; whether it’s morning talks in the well-equipped kitchen over coffee, foosball table in the game room or playing outside on our playset we hope everyone in your family has a place they can relax. PLAY hard—REST well With an extra thick King bed, 3 top rated Queen mattresses, two thick twins and an overstuffed futon, we aim to give everyone the rest they need to join in the fun!

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.

Lured to the Lake cabin w/ HOT TUB and Patoka pass

Come relax at “Lured to the Lake” cabin minutes from Patoka Lake entrance, Winery, Distillery, and Brewery! Perfect for family adventures, romantic getaways, and ladies' weekends. The cabin sits on a peaceful, wooded 3/4 ac. surrounded by gorgeous southern Indiana nature. Watch wildlife from the hot tub or enclosed back porch. A picnic table, firepit, and Blackstone grill are available for use. The cabin also has corn hole boards and an air hockey table! Short drive to French Lick/West Baden.

Lakeside Cottage

Perfect for couples! Thoughtfully designed with a soothing, rustic chic asthetic. Enjoy the peace and quiet, the wildlife, beautiful views and gorgeous sunsets from the tree tops! Propane fire pit on deck & wood fire pit in the yard with wood provided. About a 15 min drive into Owensboro which is a very cool year-round Rivertown with plenty of restaurants, shops, pubs, and especially the beautiful Riverfront Park! We are also on the Bourbon Trail! Bring your kayaks and enjoy the lake!

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.

Cozy, 2 bdrm home. Weekly and monthly rates avail.

Our sparkling clean home is located in a great neighborhood in the heart of Washington, IN. Our small town boasts of 1) Multiple dining options, 2) Coffee shops, 3) Shopping and entertainment. Or if you are wanting something a little quieter and at home you will find a host of 4) Outdoor games, 5) Bikes, and more in the storage building out back. So whether you are here on vacation or business our goal is to make you comfortable and at home while you are in our area.

Eagle Pines Cabin (Eagle Adventures LLC)

Relax w/us at our beautiful, comfortable, and private Eagle Pines Cabin. We are 12 miles from Holiday World. The Cabin has its own private hot tub and also includes a private fire pit and we supply the firewood. Cabin is stocked with everything you’ll need. Hosts are on site, but out of sight. Our other rentals are Eagles Nest (3BR option) and Eagles Nest Plus (4BR option). Starting with the 2026 season check out will be at 10 am ON SUNDAYS ONLY, 11AM all other days.

Country escape with game room!

Very spacious with lots of space for the whole family to come and spend time together. Enjoy time by the fire in the unique patio grain bin, or in the basement game room playing board games, pool, or darts. Enjoy a meal in the large spacious kitchen with ample seating space for the whole family, 3 separate living areas with smart tvs. 4 full baths, Bedrooms include 2 king beds, 3 queens and possibly 3 or 4 twin beds in the basement game room storage area.