Holiday houses 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, 114 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, 133 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
An inviting wooden porch is featured, adorned with potted plants and hanging ferns. Two chairs are positioned comfortably, offering a serene setting surrounded by greenery. Sunlight casts soft shadows on the porch floor, enhancing the tranquil ambiance of the space.
Cabin in Pineville
4.97 out of 5 average rating, 154 reviews

Outdoor Lover's Creekside Cabin (dog friendly)

Enjoy all the scenery of Bell county in this creekside cabin. Whether you prefer to hike, fish, ride sxs, or just enjoy scenery, we have it all. 3 min from Pine Mtn State Park and Wasioto Winds Golf Course, 7 min to downtown Pineville, 20 min to Cumberland Gap National Park. Kingdom Come State Park and Cumberland Falls are an hour drive. Load up your sxs or atv and ride one of the many trails right from the driveway! Black Mountain Off Road Park and Tackett Creek are also about an hour away.

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.
Guesthouse in Pioneer
4.96 out of 5 average rating, 211 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
Farm stay in Corbin
5 out of 5 average rating, 150 reviews

Scenic Farm with lots of extras & lots of room

Beautiful farm sitting on top of a mountain provides the best views! Close to everything without being in the middle of everything. 10 miles from exit 25 Corbin & Corbin Arena. 5 mi from Exit 15 Williamsburg. 8 mi to University of the Cumberlands. 13 mi to Falls or Laurel Lake. 2 fishing ponds and private maintained hiking trails. So much to do at farm or surrounding areas. Very spacious and comfortable home. We work to keep home clean and safe for you and family! Relax in peace.

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, 272 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, 278 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.

Top Guest favourite
Guest suite in Williamsburg
4.96 out of 5 average rating, 232 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

Top 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.
Guesthouse in Williamsburg
4.88 out of 5 average rating, 518 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.

Top Guest favourite
The living area includes a black couch and two patterned chairs facing a sleek coffee table. Light-colored walls are complemented by lamps beside the seating. An abstract painting with vibrant colors adds a decorative touch, and wooden accents enhance the design.
Home in London
4.98 out of 5 average rating, 303 reviews

(64) 3Bedroom Comfy Beds and MountainView home

Reunion or family event? FOUR homes side by side! Make memories in this charming home! The moment you walk through the front door, you'll fall in love with the rich beautiful Mountain View! Sit back and relax on the front porch and enjoy the evening sunset after a full day of exploring the outdoors. ✅My DIGITAL guidebook is an amazing resource ✅Spectrum Wifi ✅Smart TV ✅Coffee Bar ☕️ ✅Pack n play and high chair ✅Board games 🎲 ✅Discount for long term rentals

Top Guest favourite
Cabin in Stearns
4.99 out of 5 average rating, 109 reviews

John L. Wright Cabin

Enjoy a peaceful escape. This newly built cabin with all the modern features is located in historic Stearns, KY. Surrounded by trees and overlooking a beautiful pasture, visitors can relax and enjoy the Big South Fork and Daniel Boone National Forest hiking and horseback riding trails, kayaking, and Cumberland Falls scenic attractions. Also enjoy and view the Big South Fork scenic railway train. Security cameras are turned off when guest are occupying cabin.

Top 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, 250 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

Quick stats about holiday rentals in Williamsburg

  • Total holiday rentals

    Explore 10 holiday rentals in Williamsburg

  • Nightly prices starting at

    Williamsburg holiday rentals start at $101 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,420 verified reviews to help you choose

  • Wi-Fi availability

    10 of Williamsburg holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Williamsburg rentals

  • 4.9 Average rating

    Williamsburg stays are highly rated by guests—averaging 4.9 out of 5!

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