Holiday houses in Anchorage

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Top-rated holiday rentals in Anchorage

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
An outdoor fire pit is surrounded by several wooden chairs, providing a gathering space for relaxation. The calm waters of the Ohio River reflect the night sky, with soft lights from boats creating a serene atmosphere. Low greenery and gentle clouds frame the scene.
Guest suite in Jeffersonville
4.95 out of 5 average rating, 247 reviews

RIView 103. Modern Waterfront Suite Kentucky Derby

Guests can enjoy scenic views of the mighty Ohio River from any room in their private suite. Catch a beautiful sunrise or relax while sitting on the porch watching the boats and barges cruise the river. Close drive to interstate to get you to downtown Louisville to enjoy a dinner, museum, basketball game or concert in the KFC YUM Center and the world famous Churchill Downs! 1 mile away from River Ridge. We do offer a Tesla only charger or you can bring your own standard attachment for a charge.

Guest favourite
Home in Jeffersonville
4.98 out of 5 average rating, 143 reviews

Walking Bridge, Putt Putt House

NEW LISTING: Welcome to our walking bridge home on Pearl St. We have a hot tub, putt putt, and all the fun you can think of in one home. Steps away from restaurants, shopping, and bars, as well as the walking bridge to Louisville. This home is closer to the fun in Louisville than most neighborhoods in Louisville itself. Go out or stay in, you're guaranteed to have a great time in this newly renovated gem. We have high quality mattresses, and smart TV's in both bedrooms and the living room.

Top Guest favourite
The exterior of a historic two-story brick home is showcased, framed by lush greenery and vibrant flower planters. A stone pathway leads to a welcoming front porch, while expansive lawns on either side enhance the serene outdoor atmosphere.
Cabin in Louisville
4.98 out of 5 average rating, 299 reviews

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.

Top Guest favourite
Home in Bedford
4.99 out of 5 average rating, 227 reviews

Atoka Farms

If you are looking to get away in seclusion and be with Mother Nature, this is the home. Very quiet, with a running creek beside the home. Walking distance to the Ohio river, two outdoor decks, one with a grill. A car port, full kitchen, two full baths, paved driveway, trees all around. The home sits between two hill ridges surrounded by 180 acres. It is a park like setting. 30 minutes from Gene Snyder and I-71 (Louisville). Historic Lagrange Ky and Madison In, are a must see and close by.

Top Guest favourite
An outdoor deck provides a serene seating area with a round table and four metal chairs, overlooking the calm river. The surrounding trees and distant urban skyline create a peaceful backdrop for relaxation.
Home in Louisville
4.96 out of 5 average rating, 178 reviews

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

Top Guest favourite
A modern kitchen features dark cabinetry paired with a bright countertop and contemporary appliances. Natural light enters through large windows, illuminating the adjacent dining area furnished with a sleek table and metal chairs, set against a backdrop of greenery.
Home in Louisville
4.98 out of 5 average rating, 129 reviews

Charming Bungalow on 1.5 Acres in Amazing Location

Peaceful. Private. Clean. Comfortable. Convenient. Hummingbird is a charming updated bungalow in one of Louisville's most coveted neighborhoods. Nestled on 1.5 acres of a historic street, you'll enjoy a park-like setting teeming with wildlife. Private, yet offering easy access to shopping, dining, entertainment, and major highways, this hidden gem is sure to please. Plus, NO CLEANING FEE! Whether here work, fun, or both, you’ll love your time at Hummingbird.

Top Guest favourite
The inviting bedroom features a spacious bed with white linens and a soft green throw. A mounted projector is positioned on the ceiling, with greenery-patterned wallpaper creating a serene ambiance. Two bedside tables with lamps and a bench at the foot of the bed enhance functionality.
Guest suite in Louisville
4.99 out of 5 average rating, 227 reviews

Olive Branch Suite with projector screen in E Lou

This suite is a beautiful private retreat complete with a projector for watching your favorite streaming service for the ultimate movie night. Centrally located and within 10-20 minutes of numerous local hospitals, universities, as well as various restaurants and downtown destinations, our guest suite offers a peaceful retreat in a convenient and safe location. We also provide a fold out desk that guests can use for a remote work space if desired.

Guest favourite
The exterior of the home features a light beige facade with a metal roof and a vibrant red front door. Two shrubs frame the entrance, and the porch is accessed by three steps, providing a welcoming approach. Clear skies and lush greenery enhance the setting.
Home in Middletown
4.92 out of 5 average rating, 166 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.

Top Guest favourite
A spacious living area features a large sectional sofa arranged around a circular coffee table. A neutral-colored wall holds a decorative fireplace, while soft lighting creates a relaxed setting. A television and desk are positioned on one side, enhancing the room's functionality.
Home in Louisville
4.97 out of 5 average rating, 184 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.

Guest favourite
The entrance features a black door with an oval window, framed by decorative brick. Two potted topiaries are placed alongside the door, while a wicker chair with a patterned cushion sits to one side. Warm outdoor lighting is provided by wall-mounted lanterns.
Home in Louisville
4.94 out of 5 average rating, 110 reviews

...Happy Trails House in Derby City

4 bedroom, 2 full baths, 1 half bath, ( bedrooms on 2nd floor, none on 1st floor ). Our home is on a dead end street steps away to a walking trail, fenced yard, 2 patios, charcoal grill. Only 15 to 20 min. drive to Downtown, Churchill Downs, Hospitals, Airport, close to major highways. Near restaurants, shopping centers, grocery, liquor store etc. pets welcome with $10 fee per pet per night. Washer/dryer and dishwasher

Top Guest favourite
A blue carriage house is viewed from the driveway, surrounded by greenery and blooming trees. Steps lead to an upper balcony, offering outdoor potential. The driveway provides easy access to the garage, emphasizing a sense of space and privacy.
Guesthouse in Louisville
4.93 out of 5 average rating, 1,203 reviews

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.

Guest favourite
Home in Louisville
4.97 out of 5 average rating, 317 reviews

Thompson Hideaway

Our cozy home is tucked back off the road, located directly behind the Mellwood Art Center. The neighborhood has a large selection of restaurants and one of the best bars for live music in the city Mellwood Tavern. Nulu, Downtown and the Highlands are all very close by. This home is a good option for couples, families, or a trip with friends. Great for a Travel Nurse with a dog

Popular amenities for Anchorage holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Jefferson County
  5. Anchorage