Vacation rentals in Boston

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Top-rated vacation rentals in Boston

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Top guest favorite
The exterior of the home features a charming white façade with black accents, complemented by a small set of steps leading to the front door. Lush green grass surrounds the property, and a gravel pathway is lined with decorative stones and small shrubs.
Home in Springfield
4.98 out of 5 average rating, 133 reviews

Bourbon Trail Schoolhouse

Enjoy staying in a piece of history within this old one room schoolhouse converted to a two bedroom home. Sit out on the swing or by the firepit as you enjoy peaceful sounds of the country and the creek adjacent to the property. Located right on the Bourbon Trail with only a 5 min drive to Maker’s Mark, 17 min to Limestone, and 20 min to Log Still Distillery. Venture in to the city of Springfield to learn about Abe Lincoln and his parents, married in the courthouse, still being used to this day!

Guest favorite
The image collage features various spaces of a stylish home. A cozy lounge area with a fireplace is shown, alongside an outdoor hot tub surrounded by greenery. The dining area is connected to a deck, and a game room with a bar creates an inviting entertainment space.
Home in Bardstown
4.97 out of 5 average rating, 116 reviews

StillHill: HotTub GameRoom Whiskey Lounge Acreage

Stylish 3 bedroom home located in the Bourbon Capital is a perfect getaway to be still or tour the best Kentucky bourbon from a local whiskey still. Centrally located within 25 miles of 10 distilleries! Close to the Old Kentucky dinner train, the Derby, and a short drive to Louisville & Lexington. Enjoy 5 private acres where you can soak in the hot tub, swing on the patio, sit by the fire and watch the birds and deer. Then relax in our indoor lounge or garage game room after a day of adventures

Top guest favorite
A cozy bedroom features a spacious bed with crisp white linens and decorative pillows. Above the bed, a vibrant artwork of a cow adds a touch of character to the room. A bedside lamp and a small blue nightstand provide additional comfort.
Place to stay in Vine Grove
4.99 out of 5 average rating, 160 reviews

Fort 5400

Rustic 1 bedroom unit on 6 acres. Beautiful creek a couple hundred yards from your door with lovely sunsets. Vaulted living room, dual reclining sofa, 50 inch ROKU TV & dinette. Kitchenette with full size refrigerator, microwave, and Keurig coffee maker. King size bed, cozy electric fireplace, 32 inch ROKU TV and closet with washer/dryer. The grounds are shared with one other tenant. FT Knox-6.2 Miles Elizabethtown Sports Park-15 miles Church Hill Downs-36 miles Boundary Oak Distillary-7 miles

Top guest favorite
Farm stay in Elizabethtown
4.99 out of 5 average rating, 132 reviews

Mini Cow Cottage! Peaceful Farm Getaway

Come enjoy this peaceful private getaway in a beautiful country setting that is still close to town and the bourbon trail. The cottage offers two bedrooms (one king, one queen) and one bath with an open floor plan, fully stocked kitchen, W/D, front and back covered porches, and don't forget the animals! We have mini Highland and High Park cattle, a horse, friendly barn cats, and spacious natural surroundings. There is also a walking trail along the woods, and a beautiful pond. Dogs welcome too!

Guest favorite
A cozy living area is highlighted by a large, plush bean bag chair and a comfortable sofa. A wall-mounted TV is positioned near a small table. Light-colored walls contrast with the dark furniture, while natural light enters from a nearby doorway.
Townhouse in Elizabethtown
4.98 out of 5 average rating, 275 reviews

Bear-BnB - Relaxing Bear Themed Space

You will be close to everything in Elizabethtown when you stay at this newly remodeled, centrally-located place with a Bear theme. Unique amenities unlike any experience Including: 1Gb Fiber with WiFi, 55" QLED TV, Nest Thermostat with Smoke & Carbon Monoxide, LoveSac Sactional with LoveSac SuperSac coined the ":Bear Chair", Keurig D-Duo Coffee, premium Therapeutic brand mattresses. Full Laundry, and Flywheel Exercise Bikes, Weber Natural Gas Grill and Outdoor Seating area. Included Laundry

Top guest favorite
A comfortable living area features a brown leather sofa adorned with plaid cushions, accompanied by a light-colored armchair. A round coffee table rests on a patterned rug, displaying magazines. Indoor plants and a decorative lamp add a touch of greenery and light to the space.
Farm stay in Loretto
4.99 out of 5 average rating, 511 reviews

The Barrel Head

* LOCATED RIGHT ON THE BOURBON TRAIL * At the Barrel Head bed, we strive to make our guest feel as comfortable as possible. This location has been newly remodeled and furnished; a brand new queen size bed, pull out sofa, and coffee bar ensure that you are getting the sleep and energy you need for all of your endeavors while staying on the Bourbon Trail. The Barrel Head is also handicap accessible. There are not any steps, and we have installed a walk in shower for anyone in a wheel chair.

Top guest favorite
A wooden deck leads to the entrance of the cottage, surrounded by lush greenery. A concrete patio features a circular table with benches, providing a shaded outdoor space. The natural setting creates a serene environment, with trees framing the view.
Cottage in Hodgenville
4.98 out of 5 average rating, 248 reviews

Basil Cottage on the Creek

The Basil (baz-el) cottage is the perfect get-a-way where you can sit on the back porch sipping coffee while overlooking the babbling creek- get back in touch with nature for a much needed break from the stress of every day life. It may be a much needed romantic weekend, a mid- way point as you tour the bourbon trail, visiting Lincoln's childhood home or just a place of your own while in town to visit family, no matter what brings you to our cottage- you will love it here.

Top guest favorite
The cottage is nestled among lush greenery, showcasing a unique design with corrugated metal and concrete. A wooden deck leads to the entrance, surrounded by neatly arranged flower beds. Windows provide ample natural light while blending harmoniously with the woodland surroundings.
Cottage in Coxs Creek
4.96 out of 5 average rating, 156 reviews

Bourbon Way Cottage

Unique cottage nestled in the woods located along the Bourbon Trail. Centrally located near miles of nature trails in Bernheim Forest & many of the distillery tours. Yet lots of privacy on 10 wooded acers. 8 minutes to Jim Beam Distillery, 8 min to Bernheim Forest, 4 min to Four Roses Bourbon Warehouse & Bottling Tour, 12 min to the City of Bardstown, 30 min to Churchill Downs, 26 min to Louisville International Airport (SDF) NO SMOKING NO PETS

Top guest favorite
Dome in Mount Washington
4.98 out of 5 average rating, 226 reviews

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.

Top guest favorite
A cozy cabin is framed by lush greenery, featuring a wrap-around porch with decorative lights. Large windows offer an inviting glimpse into the interior, while a wooden exterior blends harmoniously with the natural surroundings. A spacious lawn enhances the serene atmosphere of the property.
Cabin in Hardin County
4.97 out of 5 average rating, 371 reviews

Cabin at Calico Springs

Welcome to The Cabin at Calico Springs, located on 150 acres with nine natural springs, a stream that runs year round, hiking trails, and beautiful forests. This cozy cabin features a great room with living, dining, and kitchen space. There is a private bathroom. The loft has a queen, a bunk bed (2 twins) and a twin. The downstairs has a wrap around porch with room for dining, swinging, and relaxing.

Top guest favorite
A spacious living area features a black leather sectional sofa and a wooden bar with stools. Tile flooring extends throughout the room, which is illuminated by ceiling lights. Walls are decorated with framed artwork, and there are double doors leading to a closet.
Apartment in Shepherdsville
4.93 out of 5 average rating, 164 reviews

For the ones who serve

We decorated and dedicated this place in honor of my father who served in WW2 as a Marine. He passed March of 2020. We have all type of military things along with other unique pieces. We plan on always coming up with more things to change it around. This is a part of a duplex which sits on the property with our wedding venue. Check out our guide book for local attractions and mileage

Top guest favorite
Home in Bardstown
4.97 out of 5 average rating, 264 reviews

On The Rocks - now with a Hot Tub!

Enjoy beautiful sunrises and sunsets on a quiet country road only minutes from downtown Bardstown. Enjoy the sounds of nature on our large outdoor patio. Relax in the Hot tub after a day of touring the area or enjoy visiting with our horses who may show up at the fence for a peppermint or carrot. This house is great for family get aways or couples wanting to traveling together.

Popular amenities for Boston vacation rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Nelson County
  5. Boston