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, 182 reviews

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

AngelaRating, 5 stars3 weeks ago

We love this place! Stayed here in 2022 and again this year. The hot tub was awesome and perfect for watching the stars at night. There was plenty of room for everyone and they supply EVERYTHING! Melanie was super responsive throughout our trip. There was plenty to do in the area during our trip as well. This is a gem of a place and we really enjoyed our stay!

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

A sheltered pavilion with a green metal roof is positioned along the waterfront. Stone columns support the structure, and views of the Ohio River can be seen in the background. Surrounding trees provide shade, enhancing the peaceful outdoor setting.

Home in Owensboro

4.95 out of 5 average rating, 126 reviews

The Cozy Cottage

TommyRating, 5 stars2 weeks ago

Benita and Mike were one of the best hosts I’ve hade. They were very responsive and helpful during my stay. There was an issue with the washing machine , and before it was quickly remedied, Benita and her husband made sure I was able to do my laundry was taken care of after hours. Truly excellent hosts and very hospitable. I will definitely be reaching back out when I return to Owensboro. 10/5 stars.

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, 27 reviews

The Moonlight Hollow - Moonlight Haven

JanetRating, 5 stars1 week ago

Thoroughly enjoyed staying in the cozy, fun styled camper. Moonlight Hollow was a gem. The hosts are informative, gracious and friendly. The location is quiet and peaceful . The beauty of the farm and nature de-stressed. Very clean with comfortable bedding. I left with farm fresh eggs and contentment.

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, 133 reviews

The Getaway House

AlyssaRating, 5 stars1 week ago

had a great stay in loogootee! we only came through for one night but it was just what we needed! the layout of the home is rather unique but totally fine. i will say, if someone who stays in the front bedroom had to go to the bathroom, they would’ve had to go through the back bedroom or the garage which was odd to me. but, we had a great stay though!

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Popular amenities for Winslow vacation rentals

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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 stars1 week 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, 121 reviews

The little big cozy house

KrystalRating, 5 stars1 week ago

Place was very nice and smelled wonderful upon walking in! Loved the fenced in backyard for my fur baby! Francisco was very prompt with any responses and answered any questions we had! Thank u again we would book again absolutely!

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 stars7 months ago

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

Top guest favorite

A two-story house is surrounded by green grass and large trees, offering shade. A circular seating area with multiple chairs is positioned on a pebbled surface, creating a cozy outdoor space. The property showcases a country setting with a clear sky in the background.

Home in Dale

4.97 out of 5 average rating, 35 reviews

Amazing View Christmas Homestead

AllisonRating, 5 stars8 months ago

My family stayed here for 4 nights and it was perfect. The game room/second living room was a perfect area for the older kids to hang out at. The place is very accommodating with everything you need. The location was perfect to go to holiday world and secluded with no worries about traffic with kids outside. Would definitely recommend staying here!

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, 140 reviews

Cottage by the River & Convention Center

NicRating, 5 stars3 weeks 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, 8 reviews

Huge Home for Everyone!

KarinaRating, 5 stars3 weeks ago

The house was lovely and well appointed. We had everything we needed to fix meals and plenty to entertain us.

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