Holiday rentals in Williamsburg

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Top-rated holiday rentals in Williamsburg

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Top guest favourite
The exterior view of The Arvilla showcases a single-story home with white siding and wooden pillars. A wide walkway leads to the front door, framed by symmetrical windows. The front yard features well-maintained greenery and autumn foliage in the background.
Home in Williamsburg
4.96 out of 5 average rating, 107 reviews

The Arvilla: Two Bed One Bath Home

The Arvilla is a generational born again coal mining home that belonged to my great grandparents. It was the meeting place of my grandparents while my grandfather finished college and pastored at a local church. The house was left to my grandmother and we are now blessed with this piece of history. Over the decades, there has been a lot of family love within these walls and we are excited to share everything this cozy space has to offer. Welcome to Williamsburg, where everything feels like home.

Top guest favourite
A vibrant welcome wreath adorns the front door, featuring a mix of colorful flowers and greenery. A small wooden sign reading 'Welcome to The Dorothy House' is prominently displayed at the center, creating an inviting entrance.
Home in Williamsburg
4.99 out of 5 average rating, 122 reviews

The Dorothy House - Williamsburg, KY

The Dorothy house is in a great location. It is only 1.6 miles from Williamsburg Waterpark and The Mint, and about 2 miles from the University of the Cumberlands, Walmart, and downtown Williamsburg. It offers a country setting, but it is within driving distance of area attractions, such as Cumberland Falls State Park (20 miles) and Big South Fork National Forest. It offers the best of both worlds. It is great place just to relax; sit on the porch or deck and watch for wildlife or read a book.

Top guest favourite
A newly built cabin is nestled in a secluded forest setting, with a small creek flowing beside it. The cabin features a blue metal roof and a front porch. Sunlight casts shadows of trees on the grassy area, enhancing the tranquil scenery.
Cabin in McKee
4.99 out of 5 average rating, 294 reviews

The Cabin on Panther Branch

Drive down Kentucky scenic highway 89 South just 9 miles south of McKee. The cabin is newly built and set back in a secluded area with a small creek running right beside the cabin and a larger creek just across the road. The Cabin on Panther Branch is a perfect place to come fish and kayak on the creek. Bring your ATV’s, side by side or dirt bikes and enjoy miles and miles of riding in S-Tree Tower in the Daniel Boone National Forest. We don’t think you will be disappointed with your stay.

Guest favourite
Large windows frame the serene view of surrounding trees, allowing natural light to fill the space. A spacious bed is positioned in the foreground, offering a comfortable place to relax while enjoying the peaceful greenery just outside.
Tiny home in Corbin
4.95 out of 5 average rating, 312 reviews

Cozy Cumberland Cabin

Tiny Cabin on the edge of Daniel Boone National Forest. Ten minutes to Cumberland Falls, fifteen minutes to Grove Marina at Laurel Lake, and ten minutes to hiking trails. Located on 5.5 acres, this beautiful wooded land can offer privacy or room to bring some friends. Designed to be simple, attractive, stylish, and clean, with large windows to bring the outside in for a relaxing environment. Large porch to escape the mosquitoes, fire pit for use to keep warm, and plenty of space to explore.

Top guest favourite
A cozy living room is shown, featuring a gray sofa and patterned armchair arranged around a low coffee table. A large TV displays an image, and warm light is provided by a floor lamp in the corner. Natural light filters through the bright window treatments.
Home in Corbin
4.97 out of 5 average rating, 204 reviews

Cozy Corbin Cottage

Enjoy a stay in this newly renovated Corbin home in a quiet residential neighborhood. 2 bedrooms and 1.5 bathrooms with a host of amenities including WiFi, 65” tv with cable and streaming services, a well-equipped kitchen, and more. Adjacent to Corbin High School, you may walk to public-access tennis courts and walking track. This location makes a great launching point to many area attractions such as: Corbin Arena Laurel Lake Cumberland Falls State Park Cumberland Run racetrack And more….

Top guest favourite
The kitchen features modern gray cabinets and a wooden table set for two. A coffee maker and kettle are visible next to a window, while a white stove and clock adorn the wall. Soft lighting creates a welcoming space in the log cabin's rustic setting.
Guest house in Pioneer
4.96 out of 5 average rating, 201 reviews

Appalachian Mountain Log Cabin (Private Retreat)

The Cabin at GoodSoil Farm is the perfect solo get-a-way from it all! This cozy hand built log cabin is just right for reading, reflecting, retreating, or just resting. The Cabin sits as the centerpiece of our working mini-farm and comes replete with rocking chairs on the porch, a gurgling creek nearby, a stunning mountain view, and room to explore. Read a book, strum your guitar, prop up your feet, put on some coffee & leave your cares behind for a few days at The Cabin on GoodSoil Farm.

Top guest favourite
A tiny home features a bright orange facade with a welcoming porch. A white door is flanked by a window, and steps lead up to the entrance. Surrounding grassy spaces are dotted with trees, and a fire pit is visible nearby.
Tiny home in Gray
4.96 out of 5 average rating, 253 reviews

Sleeping Turtle Tiny Home

We provide an escape that is situated near a spring lake with beautiful mountain views. It is located just over 11 miles off of the I75 exit. During the day you can find yourself searching out some local activities such as Cumberland Falls, Colonel Sanders Museum... When you're ready to relax; just sit back, make a campfire to roast marshmallows or fire up the barbecue grill! This is a former paylake and no longer used for fishing except when private events have booked the entire property.

Top guest favourite
A cozy sitting area is featured with two swivel rockers positioned near a wooden shelf and kitchenette. Natural light enters through large windows, and soft lighting is provided by string lights overhead. A decorative rug lies beneath the chairs, enhancing the inviting space.
Cottage in Pioneer
4.99 out of 5 average rating, 268 reviews

The Ambleside Cottage

The Ambleside Cottage offers full privacy for a single or a couple looking for a serene getaway surrounded by the beauty of the Appalachian mountains. This magical cabin is conveniently located for travelers, yet Ambleside feel like a remote retreat nestled in the woods above Elk Fork Creek. The Cottage is an adorable tiny house, offering 500 square feet of living space with a kitchenette, a sitting area, and a bathroom with a shower. The queen-size bed is upstairs in the sleeping loft.

Guest favourite
The exterior of the tiny house is presented, featuring a clean driveway and well-maintained lawn. Four outdoor chairs are arranged in a cozy seating area, surrounded by greenery and shaded by trees. The building displays a modern design with contrasting black and white elements.
Home in Somerset
4.9 out of 5 average rating, 176 reviews

Tandy Tiny House

Welcome to Tandy Tinyhouse! This Adorable 1Br is Brand New and has everything you need! Very Modern Kitchen w/tiled backsplash, Microwave, Keurig, Refrigerator, Range and Granite Counters. LTV Flooring and 10ft Ceilings throughout. En-suite features a Barn door and Tiled Shower. Washer/Dryer Combo just off of the Kitchen Area. Amazing location 3 minutes to Downtown Somerset and 10 minutes to Lees Ford Marina. You will want to stay here again and again! Please leave mini split 68 or above

Top guest favourite
Guest suite in Williamsburg
4.96 out of 5 average rating, 221 reviews

Creekside Adventures

Make some memories at this unique and family-friendly place. Our guest suite is very spacious and open. Many of our guest have let us know how inviting and relaxing it is to stay in. We also have a creek where our children use to play when they were little. Kids can easily play in it when the weather is nice but please be careful on the walls and stones. We also have a pool area that is available for swimming during late May through early September. We do not allow pets. No Parties

Guest favourite
An outdoor area features a wooden gazebo with seating, illuminated by string lights. A stone fireplace provides warmth as it stands on a wooden deck, surrounded by lush greenery. The serene pool reflects the soft glow from the gathering space, creating a relaxing ambiance.
Guest house in Williamsburg
4.88 out of 5 average rating, 507 reviews

Williamsburg Poolside Homestead

Private guest house with incredible outdoor resort feel, nature, and simple homestead life. 3 miles to University of the Cumberlands. 20 min to Cumberland Falls, home of the world's only Moonbow. *NO smoking of any kind (e-cig included) permitted anywhere on the property or the entire neighborhood. Guests violating our smoking policy are subject to a minimum $400 fee for returning the house or property to smoke-free status and agree to being charged by accepting this policy.

Guest favourite
A cabin with a wooden exterior and a green metal roof is set amidst a wooded area. A spacious front deck features steps leading down to a gravel parking area. The surrounding landscape includes lush trees and natural undergrowth.
Cabin in Whitley City
4.97 out of 5 average rating, 242 reviews

The Bear’s Den

Take a break and unwind in the beautiful Smokey Mountains in southern Kentucky. We are situated less than 5 miles from the famous Cumberland Falls! We are close to many hiking trails and water sports. This one bedroom, one bathroom cabin boasts a full kitchen and a washer and dryer. The deck provides a peaceful view of the beautiful forest as well as a great place to relax and grill your favorite meal! An air mattress is provided for additional guests.

Popular amenities for Williamsburg holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Whitley County
  5. Williamsburg