Holiday rentals in Williamsburg

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Top-rated holiday rentals in Williamsburg

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

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Top guest favourite
A modern single-story home is set against a backdrop of tall trees. The exterior features dark siding with a metal roof. A porch with seating is visible at the front, surrounded by a well-maintained lawn.
Home in London
4.96 out of 5 average rating, 116 reviews

‘The Hill’ Convenient & Comfy!

Your family will be close to everything when you stay at this centrally-located home. Just a stones throw off I-75 and only 4 minutes to St Joe’s Hospital. There are several restaurants and activities minutes from your driveway. Boasting 3 bedrooms and 2 full baths, The Hill comfortably accommodates 6 people. The fully equipped kitchen makes it easy to whip up a meal and the dining area is a great place to gather for grub or to play a game. We hope you consider The Hill for your next London stay

Top guest favourite
A custom-built cabin is set on a grassy area, surrounded by trees. The structure features a porch with wooden railings and steps leading to the entrance, complemented by a sloped roof and decorative elements on the facade.
Cottage in Oneida
4.93 out of 5 average rating, 288 reviews

Angel Falls Retreat for nature lovers and riders!

Beautiful custom built cabin within walking or horse back riding distance to BIG SOUTH FORK. Also located within 15 minutes to BRIMSTONE REC. It’s centrally located between Bandy Creek, Leatherwood Ford, and Station Camp. There is a BSF trailhead in our community for horses/hikers/bikes/kayaks. Easily sleeps 5+ with plenty of other space for additional guests using cots/air mattress. Keep your horses in YOUR 2 stall barn right next to the house. Circle drive for trailers, toy haulers, equipment

Top guest favourite
The front of the house is framed by a grassy yard, featuring a welcoming porch with white railings. Two hanging plants adorn the porch, which has seating for relaxation. A stone pathway leads to the entrance, creating an inviting view of the home.
Home in Williamsburg
4.99 out of 5 average rating, 151 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
Home in Williamsburg
5 out of 5 average rating, 60 reviews

Modern Home with yard & Tesla Charger, Next to UC!

Spacious and modern 2BR/2BA home with extra beds throughout the home just 0.3 miles from the University of the Cumberlands. Comfortably sleeps up to 9 guests with a king bed and private en-suite bathroom, a cozy queen bedroom with a second full bath nearby, a fold-out memory foam sofa bed in the living room, plus two folding beds and a floor mattress tucked in the closets. Enjoy arcade games, smart TVs, and a fully stocked kitchen—perfect for families, students, or travelers exploring the area.

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, 322 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
Farm stay in Corbin
5 out of 5 average rating, 165 reviews

Scenic Farm -hike, fish, relax, enjoy

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. Bonfire pit. Large covered decks. Spacious, ready to live in, comfortable home. We work to keep home clean and safe for you and family! Relax in peace.

Top guest favourite
A tranquil pond reflects the blue sky and scattered clouds. Lush green fields surround the water, with trees framing the edges. The serenity of the landscape invites relaxation and exploration.
Cabin in Jacksboro
4.99 out of 5 average rating, 211 reviews

Bolton Farm Jackie’s Jewel 2 bd/1 bath

Farm experience/relax and enjoy our 15 acre little piece of heaven.Sit on the deck overlook the fish pond,watch the mini animals play in the field. View goats, mini ponies/donkeys. free gated secure parking for your atv/boat trailer. Full stocked kitchen,tile walk in shower, washer/dryer, Qn bed, queen sleeper sofa, 65” tv and gas grill on deck. 5 acre field is open to explore around pond. We love hosting please inquire about discounts on extended stays for travel nurses or remote workers

Superhost
A modern kitchen features sleek stainless steel appliances, including a refrigerator and microwave. Light cabinetry provides contrast against the dark countertops. Various utensils and kitchenware are neatly arranged, contributing to a functional cooking space.
Home in Williamsburg
4.91 out of 5 average rating, 301 reviews

Cumberland Mountainside Stay 1 mile from UC Campus

Within walking distance to University of the Cumberlands, 5 minutes (2miles) off of I-75, and less than thirty minutes from the original KFC and Cumberlands Falls State Resort Park. This home is newly renovated with 2 bedrooms and 2 bathrooms, and a bonus loft bedroom for 4! Comfortable, plush living room furniture makes for great space to wind down after a day of adventuring in the beautiful Southeastern Kentucky mountains. With a fully stocked kitchen, it's like home away from home.

Top guest favourite
Guest suite in Williamsburg
4.96 out of 5 average rating, 253 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.
Guest house in Williamsburg
4.88 out of 5 average rating, 547 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
Cabin in Stearns
4.99 out of 5 average rating, 124 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, 257 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

When is the best time to visit Williamsburg?

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Avg. price£84£79£88£76£73£83£85£97£85£88£86£79
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Frequently Asked Questions

  • What are the best places to stay in Williamsburg?

    Popular places to stay include vacation homes near Cumberland Falls State Resort Park, cabins tucked into wooded areas, and centrally located rentals downtown. These options allow for easy access to both natural and cultural attractions.

  • What are the best things to do in Williamsburg with kids?

    Take the family to Kentucky Splash WaterPark, hike easy trails at Cumberland Falls State Resort Park, or visit interactive children's exhibits at local museums. Parks with playgrounds and seasonal events provide additional activities for all ages.

  • What are some of the best things to do in Williamsburg?

    Discover outdoor activities at Cumberland Falls State Resort Park, relax at the Kentucky Splash WaterPark, or explore local museums and downtown shops. Seasonal fairs and markets are also part of Williamsburg’s cultural calendar.

  • How is the weather in Williamsburg?

    Williamsburg has cool winters around 30–48°F (-1–9°C) and warm, humid summers near 68–89°F (20–32°C). Spring and fall bring mild temperatures and moderate rainfall, so packing layers is frequently suggested.

  • When is the best time to visit Williamsburg?

    Late spring and early autumn are often recommended for milder weather, lower humidity, and colorful scenery. These seasons also feature local events and festivals that celebrate regional traditions.

  • What are the best places to visit in Williamsburg?

    Cumberland Falls State Resort Park is often recommended for its striking waterfall and walking paths, while the Kentucky Splash WaterPark and Hal Rogers Family Entertainment Center are popular with families. The downtown area includes locally owned shops and historic sites.

  • What are some hiking trails in Williamsburg?

    Explore scenic hiking trails in and around the area, including paths at Cumberland Falls State Resort Park and wooded routes in Daniel Boone National Forest. These trails are often recommended for forest views, river vistas, and access to natural landmarks.

  • What are some family activities we can do in Williamsburg?

    Families can spend time at the Kentucky Splash WaterPark, walk easy nature trails at Cumberland Falls State Resort Park, or enjoy interactive exhibits at local museums. Community parks and seasonal fairs round out the list of family friendly options.

  • What are some of the best day trip ideas from Williamsburg?

    Explore the trails and scenic overlooks of Daniel Boone National Forest, visit Cumberland Falls, or experience local history at small museums around the region. Nature parks and riverside recreation areas also make for frequently suggested excursions.

  • Are there any pet friendly accommodations available in Williamsburg?

    Williamsburg has pet friendly vacation rentals, including some cabins and homes that welcome dogs and other companions. Some outdoor parks and trails around the area are also known to accommodate pets on leashes.

  • What are some local tips for visiting Williamsburg?

    Bring comfortable walking shoes for exploring both city streets and natural trails. Checking local event calendars and packing for changing temperatures—especially during spring and fall—is often suggested for a smooth visit.

  • What is Williamsburg known for?

    Williamsburg is known for its proximity to natural attractions such as Cumberland Falls, often called the 'Niagara of the South.' The city has a locally rooted community, university events, and connections to the Cumberland River's outdoor experiences.

  • What are the best hidden gems to explore in Williamsburg?

    Hidden gems near Williamsburg include quieter trails in Daniel Boone National Forest and locally owned eateries around the downtown area. Small art galleries and community exhibits sometimes showcase regional crafts and traditions.

  • What are the best foods to try in Williamsburg?

    Classic Southern dishes, barbecue, and homemade pies are frequently suggested in Williamsburg. Some restaurants also serve Appalachian-inspired specialties and locally sourced ingredients.

  • What should I bring for a trip to Williamsburg?

    Pack layers to adjust to variable temperatures, especially in spring and autumn, and sturdy shoes for hiking or outdoor exploration. A rain jacket and reusable water bottle are often useful for both city outings and nearby parks.

  • What is the nightlife in Williamsburg like?

    Williamsburg has a relaxed evening scene with locally owned restaurants, quiet bars, and occasional live music or community events. The focus tends to be on casual gatherings and local entertainment rather than late-night venues.

  • What are the most popular events or festivals in Williamsburg?

    Williamsburg has community celebrations around Independence Day, seasonal fairs, and local music gatherings during summer and autumn. University events and regional craft festivals are frequently suggested for visitors interested in local culture.

  • Are there family friendly vacation rentals in Williamsburg?

    Williamsburg has a mix of family friendly vacation rentals, including spacious cabins and homes near natural parks or downtown. Many accommodations provide kitchens, multiple bedrooms, and easy access to outdoor activities.

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 £45 per night before taxes and fees

  • Verified guest reviews

    Over 1,350 verified reviews to help you choose

  • Wifi availability

    10 of Williamsburg holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Williamsburg rentals

  • 4.9 Average rating

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

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