Holiday houses in Winslow

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Top-rated holiday rentals in Winslow

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

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Top Guest favourite
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, 151 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 favourite
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, 45 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 favourite
A gravel parking area is surrounded by lush trees, with a cabin visible in the background. Adirondack chairs are arranged around a fire pit in the foreground, creating a space for gathering. Bright blue skies with scattered clouds enhance the serene atmosphere.
Cabin in French Lick Township
4.98 out of 5 average rating, 196 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

Top Guest favourite
An aerial view captures a serene swimming pool surrounded by a spacious patio. A separate guest house is visible near the pool, featuring a sloped roof and multiple windows. Lush landscaping offers privacy, while a clear pathway leads from the pool area to the nearby road.
Guesthouse in Evansville
4.87 out of 5 average rating, 247 reviews

Private Guest House close to everything!

The Private Guest House is set on our property which is located on a corner (1.5 acre lot) close to the east side of Evansville. The convenient large circle drive makes it easy to enter and exit. The east side of Evansville offers Malls, Shopping, Restaurants, Bars, Entertainment, Gyms, Starbucks, and Theaters. The property is located only 10 minutes from Downtown and the Ford Center due to close proximity to Lloyd Expressway. Check out the Casino and Riverfront if you’re in the Downtown Area!

Top Guest favourite
A cozy master bedroom features warm wooden walls and ceiling, enhancing the natural ambiance. A king-size bed is adorned with a patterned blanket and complemented by wooden furniture. A mirror and map artwork are visible on the walls, with a small window allowing natural light to enter.
Loft in Huntingburg
4.93 out of 5 average rating, 232 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 favourite
A cozy living area is showcased, featuring a gray sofa adorned with patterned cushions. A wooden coffee table sits on a decorative rug, with a potted plant nearby. In the background, a partially visible kitchen area and art pieces add a touch of warmth to the space.
Home in Newburgh
4.97 out of 5 average rating, 116 reviews

RiverTown Retreat – Cozy 2BR Near River & Downtown

This is our personal home we use when lucky enough to be in the area. Our daughter married a sweet young man from here & we fell in love with this beautiful, friendly community and its adorable waterfront and downtown areas. We designed everything about this cottage to be exactly what we want & need, & we hope you appreciate all our thoughtful touches. Relax at this peaceful place to stay & enjoy Newburgh! Our location is also a great base for exploring Evansville, Owensboro, & Henderson.

Guest favourite
A spacious living area features a large sectional sofa in neutral tones, complemented by a cozy accent chair in teal. Two side tables with lamps are positioned beside the sofa. Natural light streams in through two windows, illuminating the soft carpet.
Apartment in Oakland City
5 out of 5 average rating, 7 reviews

College Town Comfort

Our 2-bedroom apartment is located in close proximity to Oakland City University. This family friendly retreat offers a cozy and inviting atmosphere for you and your loved ones. With ample space, modern amenities, and a convenient location, it’s the perfect place to relax after a day of exploring the campus and nearby attractions. Whether you’re visiting for a college tour or a business trip, our apartment provides the comfort and convenience you need for an enjoyable getaway.

Guest favourite
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
4.9 out of 5 average rating, 131 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 favourite
A fireplace with a decorative screen is centered against a white brick wall, complemented by a large wall clock above. Two small windows on either side allow natural light to fill the space. A cozy seating area and television are positioned nearby.
Home in Washington
4.91 out of 5 average rating, 104 reviews

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.

Top Guest favourite
A historic brick building stands on a cobblestone street, framed by mature trees and shrubs. The entrance features a set of stairs leading to double doors adorned with decorative glass. A lamppost adds charm to the inviting outdoor space.
Apartment in Evansville
4.95 out of 5 average rating, 238 reviews

Victorian 1 Bedroom Guesthouse Apt on 1st Street

This one-bedroom / one-bathroom apartment features high ceilings and exposed brick and is attached to your host’s home - a Victorian townhouse on one of Evansville’s historic cobblestone streets. Enjoy easy self-check-in and a location that is centrally located near the Ohio River, Downtown Evansville, and Haynie’s Corner neighborhoods. The Ford Center, Bally’s Casino, and many of Evansville’s best restaurants and bars are all a short walk away.

Superhost
A cozy living room features a light-colored sofa, a glass coffee table with a wooden base, and a decorative wall art piece depicting trees. Natural light enters through a window with patterned curtains, illuminating the textured carpet and wooden paneling.
Home in Petersburgh
4.64 out of 5 average rating, 22 reviews

Hopper Hideaway

This is a nicely remodeled mobile home located in Petersburg, Indiana. It is in a nice quiet mobile home park with paved access road. The home is 3 miles from IPL Petersburg Generating Station. It has central air and heat as well as WiFi availability. It has 2 bedrooms each with full size beds and 1 bath. It includes washer and dryer use and full kitchen as well. There are several great restaurants close by if you prefer eating out.

Guest favourite
A white single-story house is framed by lush green landscaping. Two windows with gray shutters are visible on either side of the front door, which is painted in teal. A pathway leads to the entrance, surrounded by tall grass and leafy plants.
Apartment in Evansville
4.79 out of 5 average rating, 349 reviews

Best Value/Sleeps 4/ Cozy/Center Town /Pets ok!

This is a private unit, but There is a GUEST SUITE attached to this listing (also available on Air BNB.) However, there are NO shared spaces. Each listing has a separate entrance. Near shopping, restaurants. 1Bedroom-2 queen beds-1bath cable/wifi, stocked wi/ snacks & amenities. Key lock box entry, Washer/Dryer. Couch folds down with a pull out feature on the base see pics or contact us to operate.

Popular amenities for Winslow holiday rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Pike County
  5. Winslow