Vacation rentals in Winslow

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Top-rated vacation rentals in Winslow

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

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Top guest favorite

The single-story home features a charming yellow exterior, complemented by well-maintained grassy areas and large trees providing shade. A spacious driveway leads to a garage, while large windows allow natural light to enter the inviting interior.

Home in Huntingburg

4.99 out of 5 average rating, 140 reviews

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).

Top guest favorite

A serene landscape features a lush, green lawn surrounded by trees and two reflective lakes. The tranquil scene invites relaxation under a clear sky, with gentle sunlight filtering through the leaves.

Home in Winslow

5 out of 5 average rating, 42 reviews

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!

Guest favorite

A view from above captures a six-person hot tub with inviting blue water. Nearby, a circle of Adirondack chairs surrounds a fire pit, all nestled in a wooded area illuminated by warm string lights hanging overhead.

Cabin in Eckerty

4.98 out of 5 average rating, 120 reviews

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.

Top guest favorite

The exterior of a two-story house is shown, featuring a covered porch with two blue chairs. The white siding and gray stone accents create a clean appearance, while well-maintained landscaping complements the inviting entrance. Windows are evenly spaced along the upper and lower levels.

Home in Lynnville

5 out of 5 average rating, 32 reviews

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.

Superhost

A living room area features a dark blue sofa adorned with patterned cushions. A circular coffee table is positioned in front of the sofa, which rests on a textured area rug. Natural light filters through nearby windows, complemented by light curtains.

Apartment in Princeton

5 out of 5 average rating, 3 reviews

Princeton Place | QUEEN 2BD/1BA Apt

Be our guest in this 2-bedroom, 1-bathroom apartment just minutes from TMMI (TOYOTA) and all the restaurants and amenities in Princeton. This is a simple, affordable option ideal for traveling professionals who want more than just a hotel stay. 🛌 What You’ll Enjoy: 🛏️ 2 comfortable bedrooms 🚿 1 clean, functional bathroom 🧺 In-unit washer and dryer ⚡ Fast, reliable Wi-Fi 🍽️ Fully stocked kitchen 🚗 Free street parking 📍 Convenient location near TOYOTA and Princeton

Guest favorite

A cozy living area showcases wooden walls and ceiling, enhancing a rustic feel. The space features a dining table with wooden chairs, a kitchenette with a countertop, and a comfortable seating area with a television. Soft lighting adds warmth to the inviting space.

Guesthouse in Tennyson

4.91 out of 5 average rating, 117 reviews

Guest House with acreage to explore.

Relax with the whole family at this peaceful place to stay. The wooded property provides maintained walking trails for plenty of wildlife viewing pleasure and exercise. The property also features a swimming pond. Location is 8 miles from Lincoln State Park and Lincoln Amphitheater. 10 miles from Interlake State Off Road Recreation Area. 13 miles from Holiday World. 30 miles from Evansville casinos. This is a four season resort/stay, with long summers and mild winters.

Top guest favorite

An open living area is highlighted by wooden walls and a loft above. A spacious sofa with a soft throw blanket is present in the foreground, while a dining table and chairs are positioned nearby. Natural light enhances the warm tones of the wood.

Apartment in Fort Branch

5 out of 5 average rating, 36 reviews

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.

Guest favorite

The cabin's exterior is gently nestled among lush greenery, showcasing wood siding and a welcoming red front door. A paved pathway leads through manicured landscaping, with trees providing shade in the vicinity. The serene lake is visible behind the cabin, enhancing the natural setting.

Cabin in West Salem

4.96 out of 5 average rating, 138 reviews

Lake Cabin in the Woods

🌲Looking for a relaxing getaway? Need a peaceful stopover on your Midwestern travels? Craving tranquility in a remote setting? Look no further—Lake Cabin in the Woods is your perfect retreat! Nestled about 60 miles from both Effingham, IL and Evansville, IN, our cabin offers the solitude you’re seeking without being too far from major highways. Located between Interstate 70 and Interstate 64, it’s a serene escape with easy access to wherever your journey leads.

Guest favorite

A modern kitchen space features natural wood cabinetry and a brick fireplace. A round dining table with black chairs is positioned centrally. A retro clock adorns the dark-painted chimney. Natural light filters through the window, accentuating the welcoming atmosphere of the area.

Home in Montgomery

4.95 out of 5 average rating, 22 reviews

Home near Dogwood lake/Glendale

Gorgeous newly-renovated property built In 1850. Legend has it, Abraham Lincoln once stayed in the home when he visited this area! With only a few minutes drive to Dogwood Lake and Glendale Fish & Wildlife area, this home is perfect for your next getaway with friends, or that peaceful vacation. You are able to utilize the entire property, there is plenty of space to park vehicles or boats. We are located 8 miles from I69 and the town of Washington.

Top guest favorite

An outdoor deck features a rectangular table with a central hole for an umbrella, surrounded by four wicker chairs. Lush greenery and trees provide a natural backdrop, with a peaceful lake visible in the distance.

Cottage in Huntingburg

4.86 out of 5 average rating, 242 reviews

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

Guest favorite

A spacious living area features a large sectional sofa in warm brown tones, complemented by decorative throw pillows. A coffee table with a dark finish occupies the center, while natural light filters through sheer curtains, creating a bright and comfortable environment.

Home in Loogootee

4.86 out of 5 average rating, 106 reviews

Covel’s Cottage 3br easy checkin great location

Your family will be close to everything when you stay at this centrally-located place. Less than 1 mile from restaurants, gas stations, and grocery. The kitchen is fully stocked with condiments, Spices, coffee and cookware plates etc. there are two queen rooms and a room with two singles. The back yard has a charcoal grill, a large deck with table and a fun treehouse for the kids.

Top guest favorite

The exterior of a two-story building is showcased, featuring a red metal roof and a balcony with black chairs. A sign hangs above the entrance, while the river and sunset are visible in the background. A pathway runs alongside the building, with parked cars lining the street.

Loft in Newburgh

4.98 out of 5 average rating, 316 reviews

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. 2 complimentary drip coffees are included with your stay.