Vacation rentals in Winslow

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Top-rated vacation rentals in Winslow

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Top guest favorite

A serene bedroom features a spacious bed with light bedding and a soft gray throw. A wooden dresser is situated beside the bed, with a lamp providing gentle lighting. A Pack N Play is positioned in the room, creating a family-friendly space.

Home in Huntingburg

4.99 out of 5 average rating, 129 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, 35 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!

Top guest favorite

A wooden cabin is showcased with a welcoming front porch featuring railing and seating. The entrance is accessible by steps, and a mountain-themed sign is displayed above the door. Natural surroundings enhance the rustic charm of the structure.

Cabin in French Lick Township

4.99 out of 5 average rating, 147 reviews

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

Guest favorite

A serene view of a pond surrounded by lush greenery and tall trees. A gentle slope leads to the water’s edge, where a boat is anchored. The sky captures shades of pink and blue as the sun sets, providing a peaceful atmosphere.

Loft in Huntingburg

4.92 out of 5 average rating, 192 reviews

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.

Top guest favorite

Guesthouse in Hardinsburg

4.96 out of 5 average rating, 276 reviews

Once Upon a Time little Cabin in the Woods

Welcome to Always Ranch where this unique tiny cabin offers you a tranquil spot to relax. You will be surrounded by nature and off the beaten path. The cabin may look like a lean to but the inside is rustic and warming. We are located 20 minutes form Salem, 20 minutes from Paoli and Paoli Peak, and 35 minutes from Frenchlick Casino The kitchenette includes mini fridge, microwave, double hot plate and, grill on the outdoor firepit or grill. Boats are NOT available for guests at this time

Guest favorite

A sturdy wooden picnic table is set on a gravel surface, surrounded by a spacious grassy area. The table features a rich, varnished finish, complemented by matching benches on either side. A backdrop of trees and stacked firewood is visible, enhancing the outdoor setting.

Guesthouse in Tennyson

4.95 out of 5 average rating, 103 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

A charming outdoor area is highlighted by a wrought iron table and chairs set beneath a vine-covered pergola. A well-maintained driveway leads to a garage with an American flag displayed. A white house with dark shutters and a brick accent wall is visible in the background.

Home in Saint Anthony

4.97 out of 5 average rating, 155 reviews

Hoosier Homestead in scenic southern Indiana

The Hoosier Homestead is nestled in the gently rolling hills of southern Indiana on historic Hoosier farmland. The beauty of southern Indiana is right outside the Homestead doorstep with scenic drives to numerous points of interest just minutes away. The Hoosier Homestead provides a cozy gathering space for your family and friends. Whether relaxing inside or counting stars by the fire bowl at night, everyone loves our Homestead. It is a great place to come together!

Guest favorite

Two egg cartons rest on a wooden surface, each containing a variety of eggs in different shades. One carton features beige, brown, and green eggs, while the other is filled primarily with lighter blue and tan eggs, reflecting the organic nature of the surroundings.

Guesthouse in Dubois

4.84 out of 5 average rating, 89 reviews

Rural Studio Guest-house Overlooking Corn Fields

Relax with the family on this peaceful country-side hill in Dubois, Indiana. 17 minutes to Jasper and 17 minutes to French Lick. Patoka Lake is nearby, as well as attractions like Holiday World in Santa Claus, West Baden Casino & Resort, Big Splash, indoor karting, mini-golf, and small-town restaurants. You'll find necessities nearby, including a Walmart. We always have fresh, multicolored eggs to sell from our chickens who are also fed organically.

Guest favorite

A spacious garage features two large white doors, providing ample room for parking vehicles. The floor is smooth and concrete, and a doorway is visible in the background, leading to the exterior of the home. The space is well-lit, enhancing visibility.

Home in Loogootee

4.86 out of 5 average rating, 141 reviews

The Getaway House

Welcome to our Get Away House. Located on the edge of Loogootee, it is a very peaceful area and yet close to the local stores and restaurants. Relax with the family and spend the evening on the back patio. With two bedrooms and one bathroom, this single level home is perfect for your night away. PLEASE READ! Due to a recent storm, the back fence was damaged and has been removed and we are waiting for the new fence to be installed.

Top guest favorite

A calm lake reflects the trees and autumn colors surrounding its banks. A blue kayak rests in the foreground, offering a view of the tranquil water and the serene shoreline lined with various trees.

Cabin in West Salem

4.99 out of 5 average rating, 126 reviews

Lake Cabin in the Woods

Looking for a relaxing getaway? Passing through the area and need a place to stay? Seeking peace and quiet in a remote area? Then look no further, Lake Cabin in the Woods is the place for you! Located approximately 60 miles from both Effingham, IL and Evansville, IN, our cabin is off the beaten path but is still accessible to highways and interstates to guide your midwestern travels.

Top guest favorite

A two-story building features a spacious deck with a railing, overlooking the river. A staircase leads to the upper entrance, while a small seating area with colorful chairs is visible by the shoreline. The sky displays soft pink and orange hues at sunset.

Loft in Newburgh

4.98 out of 5 average rating, 277 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.

Superhost

Two rustic wooden rocking chairs are positioned on a porch, facing a large window that offers views of the surrounding woods. Soft natural light filters through the trees, creating a serene ambiance on the porch.

Cabin in Gentryville

4.95 out of 5 average rating, 142 reviews

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.

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Other great vacation rentals in Winslow

Guest favorite

A living area with hardwood flooring features a mounted television on the wall, providing a focal point. An archway leads to a bright kitchen area with bar stools, while a door with glass paneling connects to the outside. A small decorative plant is placed on the entertainment unit.

Home in Mount Carmel

4.95 out of 5 average rating, 20 reviews

Comforts Of Home

KimberlyRating, 5 stars1 week ago

We used the house for returning to town to see family, and friends. It was a perfect meeting spot with plenty of space. Parking was a challenge especially with any car or van, but suvs and trucks had no issue. The front porch doesn't have rails enclosing it, but it was nice to hang out on.

Top guest favorite

The living area features solid wood flooring and a ceiling fan. A large smart TV is positioned opposite two comfortable sofas and a coffee table. Natural light enters through the windows, which are partially covered by blinds. A dining area is visible in the background.

Home in Vincennes

5 out of 5 average rating, 17 reviews

Home in cozy neighborhood

NinaRating, 5 stars1 week ago

Our family had a wonderful stay ❤️ this is a Beautiful home. Thank you again Carolina

Guest favorite

A serene lakeside view is framed by lush trees. A wooden dock extends towards the calm water, reflecting the greenery surrounding the bank. The shaded area features verdant grass, inviting relaxation while enjoying the peaceful natural setting.

Cabin in Cannelburg

4.97 out of 5 average rating, 68 reviews

Private Secluded 3BR2BA Cabin/Lake 16 acres(WIFI)

CaresseRating, 5 stars1 week ago

The cabin was perfect for us! Such a relaxing and peaceful stay! The cabin was one of the cleanest AirBnBs we’ve stayed at. Host was very responsive and check in/check out was a very easy process!

Top guest favorite

A bathroom is featured with a floral shower curtain adorned with colorful flowers and butterflies. Soft turquoise towels hang on a silver rack. A white toilet and a countertop with a roll of toilet paper are visible, alongside a closed door leading to the hallway.

Home in Evansville

5 out of 5 average rating, 16 reviews

Rolling Meadows Place

HannahRating, 5 stars1 week ago

We had a fantastic stay at Rolling Meadows Place! The home was spotless, beautifully decorated, and had everything we needed and more. The kitchen was incredibly well stocked - everything from spices to a Keurig, air fryer, and even cookbooks! The fenced in back yard was also a great bonus! Check-in was easy, the neighborhood was peaceful but close to everything, and the host was responsive and kind. Truly felt like a home away from home. Highly recommend this gem to anyone visiting Evansville!

Superhost

A spacious bathroom features dual vanities with large mirrors and warm lighting. A jetted bathtub is set against a backdrop of exposed brick, complemented by elegant chandelier lighting. Natural light streams through the large window, enhancing the area's inviting atmosphere.

Loft in Washington

4.89 out of 5 average rating, 96 reviews

Lovely 3 bedroom loft apartment!

KristiRating, 5 stars1 month ago

Comfortable and beautifully decorated space. The walls don’t go all the way up the ceiling, so noise does travel, but that wasn’t an issue for us. We would definitely stay here again.

Top guest favorite

Home in Washington

4.86 out of 5 average rating, 7 reviews

Sonny’s place

RoxanneRating, 5 stars1 week ago

What a thoroughly delightful home, it felt like a sweet little cocoon of comfort and rest. This charming home is cozy and comfortable, feels like a hug. The property has peaceful green space, and a delightful patio with a grill and a swing. It was exactly what we needed for a retreat! Tom and Trina were quick to respond and resolve a small problem we had with the coffee maker, and it 'saved the day' for us! I highly recommend this adorable property to anyone who needs a pleasant, 'homey' retreat!

Guest favorite