Vacation rentals in Owensboro

4.95 out of 5 average rating, 166 reviews

A scenic view of the Ohio River is visible from the deck, surrounded by trees. The water reflects the soft colors of the sky, and the landscape features gentle hills in the distance. A railing encloses the deck, offering a safe area to enjoy the tranquility.

Home in Magnet

Ohio River Retreat (Relax Riverside With Us)

Needing a rural place to get away? This cozy 1 1/2 story, 3 bedroom, 2 bath house that sleeps 8 has a front row seat to the beauty of The Ohio River. Relax on one of our decks, relax river side by the outdoor fire pit, or watch the barge traffic from inside. The house sits within minutes of The Hoosier National Forest offering hiking / fishing and a peaceful atmosphere, 50 minutes from Holiday World, and 55 minutes from French Lick. (Pet Friendly / Strong WIFI / Gas Grill, NO WATER ACCESS)

4.96 out of 5 average rating, 141 reviews

Home in Newburgh

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!

4.98 out of 5 average rating, 136 reviews

Cottage in Owensboro

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.

4.88 out of 5 average rating, 110 reviews

Cabin in McDaniels

The Cabin at Kopple Cove! Lakefront @ Rough River

Relax with the whole family at this waterfront Cabin on Rough River Lake! Full loft game room, large bedroom with oversized log bunk beds, huge 66 foot deck, and entertainment area. Located on private lake acreage. Beach your boat on the shoreline and tie to a tree. Great area for fishing! Swingset, bonfire pit, and charcoal grills. Located very close to grocery, bait shop, and restaurants! Free use of Owners Paddle boat. Renters must have previous positive reviews on AirBNB.

4.94 out of 5 average rating, 31 reviews

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

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.

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.

4.95 out of 5 average rating, 130 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.

4.86 out of 5 average rating, 221 reviews

An outdoor deck features a rectangular table with a central hole for an umbrella, surrounded by four wicker chairs. Lush greenery and trees provide a natural backdrop, with a peaceful lake visible in the distance.

Cottage in Huntingburg

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

4.92 out of 5 average rating, 26 reviews

A shaded outdoor patio area features a sectional sofa with patterned cushions, a coffee table, and an outdoor dining space. The brick exterior and large windows provide a view of the surrounding greenery. A grill is positioned nearby for barbecues.

Home in Madisonville

Great space, no cleaning fees, City park view.

Forget your worries in this spacious and serene space. A home away from home. 3 bedrooms, each with Tv. Spacious kitchen and living room. Washer and dryer in basement. Beautiful view of lake and wildlife. Basement gives added space to stretch out. Ping pong, Ms. Pac-man, foosball, corn hole and kids toys. Advance notice for use of hammock, bicycles or kayak. Need more space, second home available next door for booking.

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.

4.94 out of 5 average rating, 141 reviews

Cottage by the River & Convention Center

Great little cottage located in the bustling newly renovated Riverfront. 3 Blocks from Convention Center & very near Bluegrass Music Hall of Fame & Museum, RiverPark Center Performing Arts, Owensboro Historical Museum, Owensboro Art Museum, Smother's Park, restaurants, shopping, churches & the Antique Mall. All in walking distance or get on the free trolley 2 blocks over. Free WIFI, Smart TVs, Free Street Parking.

4.87 out of 5 average rating, 126 reviews

A grassy backyard overlooks a river, framed by tall trees providing shade. A circular fire pit with stones is positioned centrally in the yard, inviting gatherings. The tranquil water reflects the greenery, enhancing the connection to nature.

Cabin in Falls of Rough

Waterfront Cabin with Hot Tub

Relax with the whole family in this adorable riverfront cabin. Gather around a campfire, cookout, fish, kayak, or go for a dip in the hot tub all from the backyard. And if that's not enough, take a stroll around the resort and immerse yourself in the beautiful scenery, historic falls and Green Farm, golf course clubhouse, and more! Oh and don't forget Rough River Lake and the State Park are just minutes away!

4.97 out of 5 average rating, 339 reviews

A cozy green sofa is positioned across from a window, adorned with decorative pillows. A small side table rests nearby on a patterned rug, enhancing the comfortable ambiance. Natural light streams in, illuminating the room's wooden ceiling and giving a sense of openness.

Cottage in Newburgh

Boho Burgh Cottage with full kitchen/clawfoot tub

The Original Cozy Cottage is located in the heart of downtown Newburgh, this wonderfully decorated cottage offers a full kitchen, claw foot tub, walk in closet, deck, and partial river views. Shops and restaurants within steps and only 15 minutes from downtown Evansville. *Please read all info before booking*

4.89 out of 5 average rating, 108 reviews

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

Home in the woods

Relax at our cozy little house tucked quietly in a wooded setting. Enjoy some time away, located conveniently 10 minutes from the Westside of Evansville and 15 minutes from Mt. Vernon. Take advantage of the nearly secluded space with nature all around you, in the very sought after St. Philips area!

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Popular amenities for Owensboro vacation rentals

Self check-in

Pet friendly

Laptop-friendly workspace

Gym

BBQ grill

Stay near Owensboro's top sights

Moonlite Bar-B-Q Inn18 locals recommend

Bluegrass Music Hall of Fame & Museum17 locals recommend

Spirits at The Miller House9 locals recommend

O.Z. Tyler Distillery9 locals recommend

The Famous Bistro8 locals recommend

Old Hickory Bar-B-Que8 locals recommend

Dog friendly vacation rentals in Owensboro

4.95 out of 5 average rating, 301 reviews

The charming front porch is visible, featuring two red rocking chairs and a welcoming American flag. Lush green bushes frame the path leading up to the entrance, while a well-maintained yard provides a spacious outdoor feel. A bright blue sky complements the inviting atmosphere.

Home in Beaver Dam

Country Charm

Vacation home in Owensboro

A well-maintained yard features a grassy area with a decorative lion statue positioned on the left. A fenced pathway leads to a gate, providing access to the neighborhood beyond. The background includes glimpses of residential houses, enhancing the overall sense of community.

4.93 out of 5 average rating, 123 reviews

The little big cozy house

A spacious fenced backyard is visible, featuring a manicured lawn and a shaded patio area. A dog house is positioned in the background. Various trees surround the yard, offering greenery and shade. The area is securely enclosed with a chain-link fence.

4.98 out of 5 average rating, 46 reviews

Peaceful Stay | Relax & Unwind

Guest suite in Evansville

A guest suite is displayed with a comfortable queen bed adorned with a patchwork quilt. A small kitchenette is visible, featuring a mini fridge and microwave. A bathroom is partially shown, revealing a sink and toilet. Warm green walls create a cozy ambiance.

4.81 out of 5 average rating, 242 reviews

Private Suite/Sleeps 3/Center Town/Pets OK!

4.95 out of 5 average rating, 77 reviews

Home in Huntingburg

Spacious 1450 sf 2 BR Private Suite Apartment

4.98 out of 5 average rating, 111 reviews

A modern farmhouse is shown surrounded by lush green grass and mature trees. A spacious front porch is equipped with seating. A barn with a red roof is visible in the background, complementing the peaceful rural setting.

Home in Cannelton

Pop's Hideaway

4.88 out of 5 average rating, 251 reviews

A wooden entrance is framed by a lattice structure, partially covered in snow. A small dog stands in the snowy area just outside the door, surrounded by a quiet winter scene.

Apartment in Evansville

Semper Fulgens: Historic Riverfront Home

A cozy living area features a mix of comfortable seating, including two blue armchairs and a leather sofa. A patterned area rug sits on polished wooden flooring. A dining area is visible in the background, illuminated by natural light from the window.

4.88 out of 5 average rating, 245 reviews

Brick Bungalow

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Other great vacation rentals in Owensboro

4.94 out of 5 average rating, 50 reviews

A cozy place that helps you feel right at home.

4.99 out of 5 average rating, 72 reviews

A charming single-story home is depicted with a light pink exterior and a sloped gray roof. A paved driveway leads to a two-car garage, flanked by well-maintained shrubs and small trees. Blue skies and greenery enhance the welcoming appeal of the property.

Home in Beaver Dam

Rise and Shine on Main

4.88 out of 5 average rating, 25 reviews

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

City Cottage

4.98 out of 5 average rating, 57 reviews

A fire pit area is surrounded by a gravel base, featuring two red Adirondack chairs positioned on opposite sides. A stack of logs rests nearby, and the expansive green fields and trees create a scenic rural backdrop.

Home in Madisonville

Whippoorwill Farmhouse

5 out of 5 average rating, 33 reviews

A spacious deck offers wooden flooring and seating for relaxation, surrounded by lush trees. The view encompasses the serene lake reflecting the sunset, creating a tranquil outdoor setting perfect for unwinding. Soft natural light enhances the peaceful ambiance of the landscape.

Home in Falls of Rough

On The Rocks

5 out of 5 average rating, 10 reviews

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

Huge Home for Everyone!

4.91 out of 5 average rating, 22 reviews

A cozy living area features a combination of modern and traditional elements. A ceiling fan hangs above, while a fireplace is set into a dark brick wall. Comfortable seating options include a reclining chair and a blue accent chair. A large area rug adds warmth and character.

Home in Newburgh

Modern Ranch 3 BDRM, sleeps 6 + HOT TUB