Holiday rentals in Pewee Valley

4.98 out of 5 average rating, 118 reviews

Cottage in Prospect

Cozy Cottage on Famous Kentucky Farm

Experience the beauty of Kentucky farmland with hundreds of acres to explore, including our nature trail where you might spot our beef cattle and horses. Relax on the charming front porch, watch the fireflies, and soak in the peaceful atmosphere. Our cottage features a homey and cozy feeling with two spacious bedrooms: a master bedroom with a comfortable queen bed and a second bedroom with a full-size bed, perfect for families or couples. Perfect to explore the events like the Kentucky Derby.

Guest suite in Louisville

4.94 out of 5 average rating, 277 reviews

Hide away close to everything

Recently remodeled in law suite. We just upgraded the bed to a queen size. Very private, detached garage getaway. A cozy sitting area 60" CableTV with HBO SHOWTIME and STARZ. Wet bar with fridge, ice maker, coffee maker, microwave, hot plate, dishes and some cookware. Private bath has shower and a walk in closet. This private apt. is above the garage. Outside has fenced in yard for your furry friend, outdoor fire pit and sitting area. Close to the interstate and minutes from downtown.

5 out of 5 average rating, 213 reviews

Cabin in Louisville

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

4.93 out of 5 average rating, 110 reviews

Home in La Grange

Hot Tub-King Bed-Coffee Bar-Arcade-Fire Pit!

Centrally located in La Grange, the Kindness Capital of Kentucky. Welcome to the hallmark of small towns where the train rolls down Main Street over 30 times each day. Walk to locally owned donut and coffee shops, Farmer’s market, playground with splash pad, and restaurants. Spend your day on the Bourbon Trail or Churchill Downs before relaxing in the Hot Tub. Driving distance to the Creation Museum and Ark Encounter, The Slugger Museum, Falls of the Ohio, and Mega Caverns.

4.9 out of 5 average rating, 103 reviews

Home in Crestwood

12 Guest/Top Area /Families/Park

Welcome to our Family Airbnb 1- Great Location in residential neighborhood 2- 20 Min to Kentucky Derby Museum 3 - 20 Min to Louisville Mega Caverns 4- 15 Min Evan William Bourbon 5- 20 Min Churchill Down 6- Designed for 2 guests (3 Queen Bed, 1 double Bunk bed, 1 Queen Air Mattress) 7- Free Parking (2 Cars Inside and 2 Cars Outside) 8- Fully Equipped Kitchen 9- Fast Wi-Fi 10- Quiet and Safe Area 11- Private Patio 12-24/7 Available Host 13- 2 Smart TVs 14- Laundry In Unit

4.97 out of 5 average rating, 225 reviews

Guest suite in Prospect

Private Prospect Flat

Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

4.98 out of 5 average rating, 166 reviews

Dome in Mount Washington

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

4.94 out of 5 average rating, 141 reviews

HOUSE ON HERRICK

Fully renovated home in the heart of Historic Middletown. Hardwood and tile floors throughout. Queen size memory foam mattresses in both bedrooms and a full-size blowup mattress can be used in the living room if needed. 3 blocks from Main Street where you will find restaurants, shopping, and antiques! 15 minutes from Churchill Downs! Less than 1 mile to Interstate 64 with a quick Uber ride to downtown, Crescent Hill, and the Highlands.

4.97 out of 5 average rating, 168 reviews

Newly Updated: Spacious Suite/Private Entry

My guest suite is close to restaurants, business parks, shopping and easy access to highways. Guests love this place because of the big trees, green space and private entrance. The patio is great for sipping morning coffee, reading or enjoying an evening beverage. Beautiful, quiet neighborhood is perfect for a walk/run. This spacious, comfortable suite is good for couples, solo adventurers, business travelers and small families.

4.98 out of 5 average rating, 333 reviews

Farm stay in Goshen

The Coop

This 2 bedroom house is a renovated old farmhouse located on the site of a small vegetable farm and native plant nursery. The back deck overlooks the woods, where you can watch the wild birds and keep an eye on the free range chickens. This is a quiet spot for a retreat, but also 25 minutes from downtown Louisville. The Coop has a fully stocked kitchen and comes with eggs right from our flock....

4.98 out of 5 average rating, 163 reviews

Home in Pewee Valley

Bourbon Trail*Pewee Valley *HOT TUB

Welcome to the Bourbon Bungalow, a tastefully restored farmhouse on the famous Kentucky Bourbon Trail. This southern retreat is on the outskirts of Louisville in the quaint city of Pewee Valley. A short drive to some of the states most sought after locations such as Churchill Downs, bourbon distilleries, horse parks, caves, Shelbyville, Bardstown, & more! The Bourbon trail is waiting for you!

4.95 out of 5 average rating, 711 reviews

Farm stay in La Grange

The Cottage at StoneLedge 2 bedroom/1bath

Nestled on an expansive 80 acre horse farm, the cottage is the perfect escape. Hike the 30+ acres of woods that boast a creek and waterfall. Relax on the cozy front porch while enjoying the sounds of nature. If traveling with pets please note prior approval is required and be sure to read the pet policy in 'other things to note'. Thank you for your consideration.

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Other great holiday rentals in Pewee Valley

Farm stay in Simpsonville

4.9 out of 5 average rating, 69 reviews

Spacious Home with Beautiful Views

KailieRating, 5 stars1 day ago

Great house! Far bigger than the pictures make you think. We loved our stay. It was a couple miles from the main road and therefore peaceful, quiet and plentiful with lightning bugs! Great commute to Louisville. Mattresses were extremely comfortable. So was the living room furniture. It’s not over the top full of extra amenities like some places we’ve stayed but we had everything we needed. We would stay again.

4.98 out of 5 average rating, 108 reviews

Charming Bungalow on 1.5 Acres in Amazing Location

JacobRating, 5 stars5 months ago

Fantastic stay at Hummingbird for Christmas - great host and very well thought out home.

5 out of 5 average rating, 38 reviews

Flat in Prospect

The Lyric 185 - Norton Commons

Tiffany And BryanRating, 5 stars1 month ago

Brandon and his team were hugely communicative via text, which is actually my preference, and I appreciated his assistant really helping me out w a specific ask that I had, Kayla went above and beyond, big kudos to her!!! Would *absolutely* stay there again if I ever make it back to the Derby!

5 out of 5 average rating, 7 reviews

Flat in Prospect

Cozy City Condo in Norton Commons

JaydaRating, 5 stars4 days ago

I booked Tony’s Airbnb to be close to my wedding venue. From the very beginning, his communication was a 10/10. He was extremely upfront and honest especially about the number of stairs in the condo which I really appreciated since this stay was for such an important weekend. Tony went above and beyond to make sure the place would be a perfect fit. He was very accommodating and always responded quickly whenever I had a question. I was initially concerned about parking, but it turned out to be super easy with a large lot in the back and street parking in the front. I had a really good experience and the place was clean & cute too!

5 out of 5 average rating, 11 reviews

Home in Simpsonville

The Haven Simpsonville* Bourbon Trail* 3 bed/3bath

JordanRating, 5 stars1 week ago

Just stayed at Shalane's Airbnb, and it was fantastic! Super clean, beautifully decorated, and uniquely charming. It felt like a cozy home away from home. Highly recommend if you're looking for a perfect getaway! Can't wait to return! Thank you guys for making our getaway extra special! A huge bonus was the amazing entertainment area outside, beautiful ambiance, hot tub and fire pit area!! AMAZING! 🤩

5 out of 5 average rating, 9 reviews

Red Bridge Retreat

YuriamnaRating, 5 stars3 weeks ago

We had a fantastic stay! The house was absolutely perfect, clean, comfortable, spacious, and beautifully maintained. The kitchen was incredibly well equipped with everything you could possibly need, which made cooking and mealtime so easy and enjoyable. The hot tub was a huge bonus, perfect for unwinding at the end of the day. And the house was great for kids too, with plenty of space and activities to keep them entertained both indoors and outdoors, which made the whole experience relaxing and fun for the whole family. We truly felt at home and would absolutely love to stay here again. Highly recommended!