Holiday rentals in Owensboro
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Top-rated holiday rentals in Owensboro
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Emma B's Place Close to Town and the Riverfront
Emma B's Place is newly renovated and ready for guests! Here you'll find a cozy atmosphere, comfortable beds, fully equipped kitchen, and brand new washer & dryer. The location is convenient to an award winning Riverwalk, shopping, great dining, and our central location offers a short commute to the entire city. If you prefer to stay in and relax, a 42-inch smart tv and wireless high-speed internet are available for your enjoyment. Lockbox self-entry. Your hosts live nearby if you need anything!
The Bluegrass House
Welcome y'all! Serene hot tub, fenced-in back yard (2-dog limit, extra charge). Airport shuttle (separate fee). Nestled near parks, 3 miles from Edge Ice/Sports Arena. Immerse yourself in cultural richness at Bluegrass Music Hall of Fame and Owensboro Symphony Orchestra. Enjoy free summer outdoor entertainment on the Riverfront. Holiday World (30+min). Experience southern style with breakfast at Windy Hollow Biscuit House, & ribs, mutton or burgoo at Moonlight BBQ (visited by celebrities).
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.
Bluegrass Commons
You will be close to everything when you stay at this centrally-located three bedroom two bath home right off the bypass that is a short drive to anywhere in Owensboro, KY for any business travelers. This is a brand new construction home in Bluegrass Commons neighborhood! New furnishings and the home sleeps 6 comfortably. Split bedroom with an open concept perfect for families. Fully stocked kitchen with a keurig coffee station. Large backyard perfect for entertaining or just grilling.
4bed3BR Near Conv Ctr/Fisher Pk/30to HolidayWorld
METICULOUSLY CLEAN, updated 3 bedroom home, 4 beds each with tv, private Home is 3 miles from Convention center, River Park Center, Bluegrass Museum, Science Museum, Botanical Garden. It’s also minutes from baseball fields (Fischer) 30 min to Holiday world, private and fenced backyard with lighted patio. Home is well stocked with ALL you may need! If the home is empty previous night, early check in, no charge! - Wifi - Roku TV in all bedrooms - Washer and Dryer - Stocked kitchen.
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.
Midtown Cottage- Self Check-In & Centrally Located
Enjoy your stay in Owensboro, KY in this cozy, warmly decorated home! This home is centrally located to everything Owensboro has to offer, a short drive from downtown and the award winning riverfront. Wifi and parking are included. Enjoy a stylish experience at this centrally-located home. You will enjoy relaxing either in the home or the lovely backyard space. Whether you are in town for work or play indulge in the comfort and tranquility of this modern house.
Hattie's Hill Cottage
Cottage sits behind our home (see photo). NOTE- Main house may have large groups. Pool and outside areas share spaces. Near Owensboro, Rockport, Hawesville & Lewisport. There is ONE bedroom which can be made into EITHER two California twins OR one California king -Wifi. We have a Smart TV you may use your Netflix and so on with. Kitchen is well stocked with necessities. Eating/work space is provided. Comfortable recliner chairs. Access to the grounds.
Nature Lovers Retreat
This charming cottage is the perfect getaway for nature lovers. Relax in this home’s cheerful and cozy atmosphere, located on the edge of Ben Hawes Park with over 4 miles of beautiful walking trails and 7.5 miles of bike trails in this gorgeous 297 acre forest. Enjoy all the comforts of home, including free WiFi, TV, washer and dryer, full kitchen, and free parking. This special retreat is also only 1 mile from Ben Hawes Golf Course.
The little big cozy house
The little big cozy house offers you a place where you can relax and feel at home. a spacious kitchen with all the necessary elements such as The 3 bedrooms ,that invite you to rest with very suitable beds For you to spend a magnificent and comfortable night. The patio is a space where you can enjoy a grill surrounded by family or friends. This house is an excellent location that gives you quick access to any part of owensboro.
Granny Smith's
Granny Smith's is an endearing home in the heart of Owensboro, located in a historic neighborhood. The house features one sizable bedroom, tidy living room, full kitchen, cozy dining area, and a tub/shower bathroom. There is also relaxed outdoor living areas either on the front porch or back screened in patio. Property also has a small detached carport with a driveway. There is also parking on the street.
2 bedroom w/free on-site parking. Near downtown
When you stay at this centrally located accommodation, your family will be close to everything. The backyard is fenced in and has a fire pit. The sofa has one pullout bed. The master suite has one queen bed. The second bedroom has two XL twin beds. Complete kitchen with dishwasher, plates, utensils, and washer and dryer. No more than two pets. Pets must be under 30 pounds each.
Popular amenities for Owensboro holiday rentals
Other great holiday rentals in Owensboro
The Bluegrass Barbie
Peaceful Stay | Relax & Unwind
Quite and Cozy !OPEN Last Minute! 1/9-1/11
315 West 14th street
Charming Fully Renovated 2BR Home Near Everything
Private 1 bdrm apartment in the heart of the city
Simple Comfort – Top 1% for a Reason – Book Now!
Your Cozy Retreat at Three Sisters Ranch!
When is the best time to visit Owensboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $141 SGD | $145 SGD | $149 SGD | $161 SGD | $161 SGD | $162 SGD | $165 SGD | $154 SGD | $152 SGD | $145 SGD | $153 SGD | $147 SGD |
| Avg. temp | 1°C | 3°C | 8°C | 14°C | 19°C | 24°C | 26°C | 25°C | 21°C | 15°C | 8°C | 3°C |
Frequently Asked Questions
What are the best places to stay in Owensboro?
Riverfront and downtown neighborhoods are frequently suggested for their proximity to parks, dining, and cultural sites. Staying near public green spaces provides easy access to walking trails and seasonal events.
What are the best things to do in Owensboro with kids?
Families frequently suggest enjoying the accessible playgrounds and water features at Smothers Park, exploring hands-on exhibits in the Owensboro Museum of Science and History, or joining youth crafts and art activities around downtown. Seasonal events often provide kid-friendly entertainment.
What are some of the best things to do in Owensboro?
Explore the immersive exhibits at the Bluegrass Music Hall of Fame and Museum, stroll Smothers Park along the riverfront, or discover local art at the Owensboro Museum of Fine Art. The city also has vibrant dining and live music scenes.
How is the weather in Owensboro?
Owensboro experiences cool winters, with temperatures around 26–47°F (-4–8°C), and warm, humid summers that reach 65–89°F (19–31°C). Spring and fall are often noted for comfortable, mild weather and are popular seasons for outdoor activities.
When is the best time to visit Owensboro?
Late spring through early fall is frequently suggested for pleasant weather, thriving festivals, and outdoor activities. Visitors in spring and autumn often enjoy mild temperatures and an abundance of local events.
What are the best places to visit in Owensboro?
The Bluegrass Music Hall of Fame and Museum, Smothers Park, and the Owensboro Museum of Fine Art are frequently suggested for their cultural and scenic appeal. The city’s botanical garden invites visitors to connect with regional plant life.
What are some hiking trails in Owensboro?
Explore nature paths at Ben Hawes Park or Panther Creek Park, which have walking and wooded trails suitable for all ages. Both parks feature scenic landscapes and wildlife viewing opportunities.
What are some family activities we can do in Owensboro?
Families can enjoy interactive exhibits at the Owensboro Museum of Science and History, play in Smothers Park’s inclusive playground, or participate in hands-on programs at the local art museum. Seasonal festivals often include entertainment suitable for kids.
What are some of the best day trip ideas from Owensboro?
You can explore regional historic sites, distilleries, or nearby lakes for fishing and boating around Owensboro. Nature reserves in the wider area provide birdwatching, woodland hikes, and seasonal wildflower displays.
Are there any pet friendly accommodations available in Owensboro?
Many accommodations in Owensboro welcome pets, especially around the riverfront and downtown neighborhoods. Some green spaces and parks also have pet-friendly amenities for travelers bringing their companions.
What are some local tips for visiting Owensboro?
Check community calendars for live bluegrass performances, as music is a celebrated part of life in Owensboro. Locals often suggest exploring the riverfront area for public art, events, and lively green spaces, especially on weekends.
What is Owensboro known for?
Owensboro is known for its bluegrass music heritage, annual barbecue festivals, and a revitalized riverfront featuring public parks and interactive fountains. The city also celebrates local arts and culinary traditions rooted in its regional history.
What are the best hidden gems to explore in Owensboro?
Discover locally owned galleries, quiet green spaces, or specialty shops around downtown. The Western Kentucky Botanical Garden is often recommended for peaceful walks among seasonal blooms and unique plant collections.
What are the best foods to try in Owensboro?
Owensboro has a tradition of slow-cooked barbecue—mutton is a locally rooted specialty, often paired with burgoo stew. You will also find a range of Southern-style sides, locally made pies, and sweet tea in most restaurants.
What should I bring for a trip to Owensboro?
Pack layers to accommodate seasonal changes, as temperatures can shift between cool mornings and warmer afternoons. Comfortable walking shoes, a light rain jacket, and sun protection are practical for exploring parks, festivals, and outdoor attractions.
What is the nightlife in Owensboro like?
Owensboro’s nightlife features live bluegrass performances, casual bars, and late-night eateries in the downtown area. Some venues host open mic nights, local musicians, or community events that create a laid-back atmosphere.
What are the most popular events or festivals in Owensboro?
Owensboro has the International Bar-B-Q Festival in spring and ROMP Festival, a celebration of bluegrass music, often taking place in early summer. Seasonal downtown events and community gatherings also bring music, food, and family activities.
Are there family friendly vacation rentals in Owensboro?
Owensboro has numerous family-friendly vacation rentals, especially near the riverfront and downtown areas, with many homes featuring multiple bedrooms and outdoor spaces. Travelers often find parks, museums, and playgrounds close by.
Quick stats about holiday rentals in Owensboro
Total holiday rentals
Explore 130 holiday rentals in Owensboro
Nightly prices starting at
Owensboro holiday rentals start at $64 SGD per night before taxes and fees
Verified guest reviews
Over 8,030 verified reviews to help you choose
Family-friendly holiday rentals
100 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 50 rentals that welcome pets
Holiday rentals with a pool
10 properties feature pools
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Wifi availability
130 of Owensboro holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Owensboro rentals
4.8 Average rating
Owensboro stays are highly rated by guests – averaging 4.8 out of 5!
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