Vacation 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).

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!

Historic Home by Dogwood Lake/Glendale

With only a few minutes drive to Dogwood Lake and Glendale Fish & Wildlife area, this newly renovated historic 1850s home is perfect for your next getaway with friends, or that peaceful vacation. We are located 8 miles from I69 and the town of Washington. We have outfitted our home with all the amenities and comforts to make your stay as pleasant as possible! Our property provides privacy and you will enjoy listening to the sounds of nature while sitting around a campfire with a cup of coffee

The Castle

Bring the whole family to this great place with lots of room for fun! Located 15 miles from Holiday World & Splashin’ Safari. Five minute walk to the city pool, and League Stadium, where the movie “League Of Their Own” was filmed. Also home of the Dubois County Bombers. 4 bedrooms, 3.5 baths. 4000 square feet. Above ground pool, Hot Tub, 4 Sun loungers, outdoor furniture & enclosed outdoor dining area. Spacious kitchen, Movie room, inflatable outdoor projector screen with projector.

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.

Iron Fence Farm - 2 miles from Holiday World

Forget your worries in this spacious and serene space. Newly renovated 6 bedroom, 4 bathroom house only 2 miles from Holiday World! This large vintage farmhouse can accommodate 21 people with its 6 bedrooms and 14 beds all linens included. Towels and toiletries included along with custom showers with rainfall shower heads. TVs in every bedroom. All new appliances including washer and dryer. Fully stocked game room with board games for every age. No pets allowed.

Eagles Nest Plus/Eagle Adventures LLC

Eagles Nest Plus is our Eagles Nest rental PLUS the master BR & bath. It sleeps 12, has 3.5 bathrooms plus a baby bed. It’s perfect for four families traveling together. We also have one cabin on our property that sleeps four, Eagle Pines Cabin. In 2025, the pool & hot tub are no longer shared spaces. This rental has exclusive use of pool and hot tub. For more info check out our website visiteagleadventures. We provide e'thing you'll need for a great vacation.

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.

Lakeside Cottage Getaway Fishing, Hiking, Relaxing

Enjoy the lovely setting of this romantic spot in nature. This quiet getaway comes with a full kitchen, two bedrooms, access to a lovely lake, and an outdoor deck for enjoying the view. The master bedroom has a queen size bed and a crib. The second bedroom has a twin bed and a bunk bed [twin over full]. This space is perfect for singles, couples, or even large families. Close to Patoka Lake and Holiday World. No smoking/not handicap accessible

Lake House

Close to many attractions but isolated enough you will feel relaxed with scenic and lake views. Enjoy the lake or nearby attractions. Nearby Attractions: - Buffalo Trace Golf Course (6 min) - Sultan’s Run Golf Course (9 min) - Patoka Lake Winery (19 miles/27 minutes) - Frenck Lick Casinos and Resorts /Winery (23 miles/29 minutes) -Marengo Caves (50 min) -Holiday World Theme Park (40 minutes)