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.

Guest favorite

Farm stay in Cannelton

4.98 out of 5 average rating, 45 reviews

Beech Hall Corner

This 1930s farmhouse sits on 2 acres just minutes from the Ohio River. It is the perfect place for those looking to slow down and enjoy the much simpler life in a rural area. The farmhouse has two bedrooms, one bath, full kitchen and a laundry room. Sit on the front porch and enjoy your morning coffee watching cars, jeeps, and motorcycles as they make their way along the Ohio River Scenic Byway. It also has a large rear deck, perfect for relaxing with a drink in hand overlooking the grounds.

Guest favorite

Home in Newburgh

4.96 out of 5 average rating, 140 reviews

The Cottage on W Main

Family friendly 2 bed 2 bath! Charming and convenient space in downtown historic Newburgh. Easy walk to the scenic riverfront and downtown area which includes ice cream shops, restaurants, shopping and hair salon. Short walk to beautiful Rivertown Trail! Come explore downtown Newburgh and with easy access to multiple sites in Evansville the location is fantastic! So many family amenities with no stairs inside house, stroller, pack-n-play, outlet covers, kids books, and highchair provided!

Guest favorite

Cottage in Owensboro

4.98 out of 5 average rating, 122 reviews

The Woodford Retreat Cottage

Take it easy at this unique getaway.. Completely renovated 2,000 sq ft home with a beautiful river view, 3 bedrooms, 2 family rooms, 2 full bathrooms, fully stocked kitchen. The back yard is fenced with a deck, patio table and glider. This property is located a few blocks from the Owensboro Convention Center, Bluegrass museum, and multiple downtown restaurants. This property adjoins English park. Excellent rental for a weekend of downtown adventures or just enjoying the river view.

Guest favorite

Cabin in French Lick

4.98 out of 5 average rating, 177 reviews

Warm up @ Southern Grace Cabin - cozy and private!

Located south of French Lick and minutes from Patoka Lake, Southern Grace Cabin is a western red cedar log home located on a quaint lane in the middle of our property. Panoramic views include woods and rolling meadows. The custom built log home has 3 bedrooms, 1 bath, and a custom kitchen. We're sure you'll enjoy the views from the swing or wood rockers on our expansive covered porch. Located within easy driving distance of French Lick, Paoli Peaks and Patoka Lake. Boaters welcome!

Guest favorite

Townhouse in Newburgh

4.94 out of 5 average rating, 31 reviews

Quiet home on the water downstairs duplex A

Gorgeous setting with incredible water views from this lower level one bedroom/one bath duplex unit with full bed and queen Murphy bed as well as equipped kitchen. Country living that feels like a resort with a shared deck and gazebo, water access, fire pit, fishing, hiking and wild life. Unit includes private entrance, refrigerator, range/oven, microwave, flatscreen tv, WiFi, coffee maker, dishes/utensils, pots/pans. Pets: require non-refundable pet deposit of $250.

Guest favorite

Home in Owensboro

4.96 out of 5 average rating, 112 reviews

The Cozy Cottage

Join us for a relaxing stay at the Cozy Cottage! Inside you will find everything you need to make for a cozy stay whether you’re with us for short weekend or a month. Outside you will find plenty of spaces to sit and enjoy the view of the Ohio River just 2 blocks away. The Cozy Cottage is conveniently located less than 5 minutes from downtown Owensboro and popular attractions such as the Convention Center, Bluegrass Museum, Botanical Gardens, and Jack C. Fisher Park.

Guest favorite

Farm stay in Evansville

4.88 out of 5 average rating, 26 reviews

The Moonlight Hollow - Moonlight Haven

Come camp at the Moonlight Hollow! Our homestead offers something for everyone! For you animal lovers, come meet our Kune-Kune pigs & Nigerian Dwarf goats. Chickens & Guineas free-range everywhere, while our livestock guardian Anatolian/Great-Pyrenees keep everyone in line! For the garden lovers, seasonal veggies & herbs are available at our farm stand (and farm fresh eggs!). For those seeking natural healing, grab some Moonlight Hollow Herbs & Reiki!

Guest favorite

Cottage in Huntingburg

4.86 out of 5 average rating, 210 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

Superhost

Cottage in Paoli

4.81 out of 5 average rating, 48 reviews

Beautiful Cottage w/ Hilltop Views and Pool

Beautifully designed new Hilltop Cottage with Spectacular Views. Cottage includes all new accommodations. SEASONAL POOL AND HOT TUB ACCESS. 65" TV and WiFi. This property comes with some of the best views in southern Indiana that you can enjoy from your private deck or the 2,000 s.f. concrete patio. Rain or shine, you'll love this exclusive getaway. More pics at BlueberryHillEstate.com 10 m - French Lick Casino, 4 m- Paoli Peaks

Guest favorite

Home in Loogootee

4.86 out of 5 average rating, 88 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.

Guest favorite

Cottage in Birdseye

4.95 out of 5 average rating, 101 reviews

Eagles Nest

Welcome to The Eagle's Nest built in 2021. The cabin sleeps up to 8 guests and features 2 bedrooms and a sleeping loft all featuring queen sized beds. The cabin has a well-stocked kitchen, washer/dryer, high speed internet and a hot tub. The main living area features a breakfast bar, dining area and spacious great room with large screen TV.

Guest favorite

Home in Santa Claus

5 out of 5 average rating, 12 reviews

X Marks the Spot (Green)

Your family will be close to everything in Santa Claus, IN when you stay with X Marks the Spot. Located across the road from Lake Rudolph and Holiday World. You will be able to walk/bike to any local attraction or store. Settle down after a long day at the park and enjoy the firepit and quiet atmosphere.