Holiday houses in Anchorage

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.

4.95 out of 5 average rating, 339 reviews

Cabin in Louisville

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 4 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

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.

5 out of 5 average rating, 224 reviews

Perfect for Work or Play, Close to Everything!

Whether you're here for work or play, our Airbnb offers the perfect base for your Kentucky adventures! Welcome to your home away from home! Nestled in the quiet suburbs, our modern & spacious retreat offers the perfect blend of comfort & convenience. Whether you’re here to explore the famous Bourbon Trail, work remotely, or simply unwind, you’ll find everything you need right here! Close to shopping, dining, entertainment, major highways, top bourbon distilleries and downtown Louisville.

4.87 out of 5 average rating, 211 reviews

Private EAST END gem, minutes to everything!

Cozy, East End cottage just minutes from Top Golf, shopping malls, restaurants, entertainment, and other amenities. Easy access to the expressway. Home is well appointed with granite countertops, stainless appliances, hardwood floors, and more. A seasonal creek across from the house can be heard giving the impression of a cabin in the woods with privacy and seclusion, with the convenience of city living at your fingertips. There is also a beautiful park steps away from the house.

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.

4.99 out of 5 average rating, 148 reviews

"The Brook" - Louisville

Enjoy a stay at this spacious, beautifully decorated ranch home in East Louisville. Blending organic modern decor and intentional functionality, you will feel relaxed and right at home. The home is nestled in a quiet neighborhood and yet only 1 mile from the interstate - conveniently located, a drive anywhere isn't far. Bring your crew to town to experience a day at the horse track, a bourbon tour, or a Kentucky family getaway!

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!

4.93 out of 5 average rating, 1,011 reviews

Guesthouse in Louisville

HIghlands Modern Get Away

Ideal, quiet place in the highlands. You have the apartment over the garage. You'll have a place all to yourself with most the amenities of your own home. Studio apartment with a balcony if you decide to hang out and relax for the evening. There is a cook top, but no oven in the kitchen. Park in the driveway in front of the garage. Pets are welcome, plz add them when booking.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Anchorage holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Anchorage

Private room in Jeffersonville

4.92 out of 5 average rating, 706 reviews

Zen Room minutes from downtown!

RyanneRating, 5 stars2 weeks ago

Great stay…Tamyra was so accommodating and responsive. The room we stayed in and the overall house are all so cozy and peaceful and the back yard is lovely.

4.97 out of 5 average rating, 38 reviews

Farm stay in Crestwood

Maple's Place - *charm*country*hot tub*bourbontour

DustinRating, 5 stars5 days ago

This is not your ordinary Air BNB. The remodeled farmhouse is beautiful, comfortable and peaceful. Beyond that, the host are amazing. If it’s in season you will be able to pick fresh produce from their garden and they can assist with obtaining other local meets and produce. Very kind and friendly. You will love your stay here!

5 out of 5 average rating, 63 reviews

Home in Prospect

Waterside | Geodome | Fire Table | WraparoundPorch

SierraRating, 5 stars1 week ago

This was an amazing home to be in for my graduation weekend. My family and I felt right at home. Everything was extremely clean and the hosts were very responsive. The home looks just like the photos and it’s super cozy/homey. This place is great for a family get away and pretty close to everything. I really enjoyed my stay and recommend for all.

5 out of 5 average rating, 13 reviews

Louisville Retreat w/ Deck ~ 11 Mi to Downtown!

TracyRating, 5 stars1 week ago

House was just as it was in the listing, great location close to everything, beautiful home and comfortable beds!

4.94 out of 5 average rating, 63 reviews

Cabin in New Pekin

Anjuna House - a Scandi riverfront forest getaway

ChrisRating, 5 stars2 days ago

Our stay here was very relaxing. Stunning house built snug in the woods on a river. Listening to the birds while drinking coffee in the morning was my wife’s favorite. Our girls loved the bunk room and the hammock. Small space but high ceilings and well thought out design, decor, and furniture made it feel spacious. We explored the Marengo Caves, downtown Salem, and just enjoyed slowing down for a few days. We brought food with us, and cooked all the meals. They have everything you need there to make cooking easy. We loved it and want to come back in the fall when the leaves change.

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, 7 reviews

Apartment in Prospect

Cozy City Condo in Norton Commons

JaydaRating, 5 stars1 day 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!