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

Home in Newburgh

4.96 out of 5 average rating, 141 reviews

The Cottage on W Main

scottRating, 5 stars1 month ago

This a great place to stay, the house is just right for two people. The second bedroom is great for two other people for friends to stay. Each bedroom has its own bathroom. The neighborhood is awesome, great restaurants in walking distance or a short drive. The river is nearby, 2 blocks , so you can walk along the bike trail for 5 miles . Quiet neighborhood which is nice. The kitchen had all the dishes and cooking items needed. Well stocked with supplies ie toilet paper, soap( personal and kitchen). Some spices are provided. The living room is large and a small porch. Just a awesome place to stay

Top guest favorite

A spacious covered porch features a wooden swing and several rockers, inviting relaxation. A table is positioned nearby for outdoor dining. String lights hang from the beams, adding warmth. The backdrop includes rolling green fields and trees, enhancing the tranquil setting.

Cabin in French Lick

4.98 out of 5 average rating, 183 reviews

Hot Tub- 5 Stars by Patoka Lake - French Lick, IN

MaggieRating, 5 stars4 days ago

We loved our stay here and would highly recommend it. Privacy but close to French Lick and Wilstem Wildlife Park. There are plenty of games to keep the kids busy and space to play. You can’t beat relaxing on the porch at the end of the day listening to music on the Bluetooth speaker and enjoying the view.

Guest favorite

A serene landscape showcases a calm lake surrounded by dense greenery and mature trees. The water reflects the blue sky and puffy clouds, creating a tranquil setting. Grass-covered grounds lead gently to the water's edge, offering a peaceful environment for relaxation.

Townhouse in Newburgh

4.94 out of 5 average rating, 31 reviews

Quiet home on the water downstairs duplex A

MaryRating, 5 stars4 months ago

Kaci and Chuck’s place is exactly what we needed for the week we visited family. The location was perfect and we really enjoyed how peaceful it was. We even brought our chihuahua and she loved it! It felt like a French lakeside cottage, very clean and well stocked for everything we needed. We’ve found a home away from home for when we visit family and will be back!

Guest favorite

An outdoor shower is constructed with wooden framing and metallic paneling. Water cascades from a showerhead, creating a refreshing flow. Lush greenery in the background adds a natural touch to the bathing area.

Farm stay in Evansville

4.89 out of 5 average rating, 28 reviews

The Moonlight Hollow - Moonlight Haven

TaylorRating, 5 stars1 week ago

The camper was so cozy & fun! My two friends and I had just enough space. We would highly recommend the farm experience! We loved getting to meet the piglets and baby goats! Definitely an air b&b to remember. They were great hosts and gave us such a thorough tour of the property and their farm! Such friendly people!

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Popular amenities for Winslow vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Winslow

Guest favorite

Home in Owensboro

4.94 out of 5 average rating, 50 reviews

A cozy place that helps you feel right at home.

HeatherRating, 5 stars2 weeks ago

The property was exceptionally clean and well-maintained, and Patty was incredibly responsive to all of our questions. We felt very comfortable and well-cared for during our stay.

Guest favorite

A vibrant dining table is set with a large green plate containing rice, beans, and a filled tortilla, topped with a drizzle of sauce. Glasses of beverages, chips in a basket, and various sauces accompany the meal, creating an inviting atmosphere.

Vacation home in Owensboro

4.93 out of 5 average rating, 122 reviews

The little big cozy house

KendraRating, 5 stars1 week ago

Great place and great host! Gracious enough to let us check in early due to flooding. We definitely overpacked as everything we needed was already there, including dog food & treats!

Guest favorite

A living area is highlighted by a modern television mounted on a low white console, complemented by blue LED lighting. A faux fireplace sits beneath the TV, and a comfortable blue armchair adds a pop of color. A small table and decorative wall art complete the space.

Home in Evansville

4.88 out of 5 average rating, 25 reviews

City Cottage

IrisRating, 5 stars8 months ago

Cute little house. Very clean. Close to the car show. Will stay again. Thanks for letting us stay at your home.

Guest favorite

A modern bathroom features two wood-topped vanities with white sinks, positioned beneath round mirrors. Light wooden accents contrast with the white shiplap walls, while a sheer curtain conceals a bathtub area. Soft pendant lighting adds a touch of elegance to the serene space.

Home in Mount Vernon

4.89 out of 5 average rating, 108 reviews

Home in the woods

MadisonRating, 5 stars6 months ago

I got ready at this place for my wedding with my bridesmaids and it was absolutely perfect! The host was so nice and the place was clean! Very easy check in as well. The place is very private and secluded which is also a plus! Would definitely recommend:)

Guest favorite

A charming cottage exterior features a light gray façade with white trim and a bold pink front door. Flanking the entrance, white rocking chairs are positioned on the porch. Lush greenery and blooming blue hydrangeas enhance the inviting front yard, with a stone wall and steps leading to the entrance.

Home in Owensboro

4.94 out of 5 average rating, 141 reviews

Cottage by the River & Convention Center

NicRating, 5 stars1 month ago

Easy, keyless entry. The listing was as described- great location, very well equipped kitchen, plenty of linens, beautiful river views and walking distance for fun in O’boro. Bettie was a friendly host and communicated well. We’d stay here again.

Guest favorite

A covered patio with wooden beams provides a shaded area for outdoor relaxation. A seating arrangement is positioned around a central fire pit, surrounded by potted plants and greenery. A neatly maintained lawn extends around the patio, contributing to an inviting outdoor space.

Home in Evansville

5 out of 5 average rating, 10 reviews

Huge Home for Everyone!

JessicaRating, 5 stars1 week ago

We have stayed with Brian several times now when we are in the area. Absolutly love working with him and staying at this house of his. Super friendly, worked with the crew and I, kept line of communication open.

Top guest favorite

A wooden staircase leads to the upper floor, complemented by a brick accent wall. Framed photographs and decorative items adorn the wall alongside the staircase, while a small console table, a ceiling fan, and spot lighting enhance the inviting entryway.

Home in Ferdinand

5 out of 5 average rating, 20 reviews

Eagles Nest (Eagle Adventures LLC)

Austin and SylviaRating, 5 stars7 months ago

Absolutely LOVED our stay! 10/10 highly recommend to all. Do not pass this place up. It is peaceful and private, but not too far from town (less than 10 minutes) Karen and Ron have went above and beyond with the inside of the home. Everything is labeled and very easy to navigate. Karen met us to give us a quick tour upon check in and was super responsive through our stay. The pool is amazing and worth the price alone. There are games and stuffed animals for the kids and tons of water toys and floats. Next time all we will need to bring is our swimwear! There are bathroom toiletries, kitchen utensils, many coffee options, endless towels, etc. These hosts are top tier! We will be coming back for sure!

Top guest favorite