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Holiday rentals in Castlewood

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Top-rated holiday rentals in Castlewood

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

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Guest favourite
A rustic wooden cabin is situated on a grassy slope, featuring a covered porch with railings. Two windows are framed with wooden shutters, and an American flag is visible in the background. The structure showcases a simple, natural design, harmonizing with the surrounding landscape.
Cabin in Shady Valley
4.96 out of 5 average rating, 524 reviews

Scott Hill Cabin #3

You’ll love Scott Hill Cabin because of the view, ambience, and location. There are brochures in the cabin to see what options our area has for you. The actual address of the cabin is 1166 Orchard Road. We allow pets, but just ask for prior knowledge. We are just minutes from 2 separate trailheads to the Appalachian Trail. Despite the listing saying 2 beds, it is in fact, 1 double bed. Sorry for the listing mistake. We want to extend a military discount to our past and present service members.

Top guest favourite
A striking A-frame structure is nestled among trees, featuring a sleek black exterior with vertical siding. Expansive glass windows allow for ample natural light, while a spacious deck extends outward, offering a connection to the surrounding forest.
Home in Blountville
4.97 out of 5 average rating, 135 reviews

The Ark at Zion Ranch

Nestled in the heart of a 35 acre ranch this modern A-frame offers all the essentials for a comfortable stay. Featuring 24 foot walls with floor to ceiling glass looking into a private forest. You'll find everything you need for a relaxing visit, including a fully equipped kitchen, deck, luxury and adjustable queen bed plus a twin in the loft and sofa that converts to a bed, there’s room for the family! The minimalist design makes this an ideal getaway for those seeking peace and simplicity.

Top guest favourite
Tiny home in Abingdon
4.99 out of 5 average rating, 442 reviews

Hoss’s Tiny House

The tiny house is located behind a big garage with a large gravel parking lot. It is very secluded and quaint away from the main road. The parking area is behind at the back porch on the tiny house were you can sit and enjoy peace and quiet. We are 1 mi from South Holston Lake. 2 mi from Creeper Trail, 6 mi Main Street Abingdon, 8 mi downtown Bristol, 10 mi Bristol Speedway. We have farm animals in the fields beside the tiny house that are very friendly. All the farm animals enjoy visitors.

Guest favourite
A misty landscape of rolling green mountains is visible, with dense trees lining the lower slopes. Low-lying clouds drift at the mountain peaks, creating a serene atmosphere. The scene highlights the natural beauty of the surrounding area.
Flat in Gate City
4.98 out of 5 average rating, 167 reviews

Small Town Summer Nights, Hiking Concerts Relaxing

Housed in a restored office building along the Clinch Mountain, Roberts Mill Suites offers a fully renovated loft with the comforts of home. Skylight in the living room bathes the space in natural light and provides relaxing sounds during a rainstorm The Suites are near Southwest VA treasures Natural Tunnel State Park, Devil's Bathtub and the Carter Family Fold. Minutes away from Kingsport TN and Bristol TN/VA, we offer accommodation to wedding guests, race fans, festival goers and family.

Guest favourite
The exterior of a quaint country cottage is shown, featuring a red metal roof and multiple large windows. A wooden fence lines the front, complementing the surrounding greenery and neatly maintained garden beds. The entrance is framed by a simple gate, creating a welcoming appearance.
Cottage in Wise
4.74 out of 5 average rating, 149 reviews

Verna’s Place Country Cottage Peaceful Retreat

Unwind at Verna’s Place, a quaint country cottage nestled in the mountains of Southwest Virginia. This home, located in Wise, Virginia is a little over 4 miles from the campus of UVA-Wise and less than 2 miles from the local winery. Enjoy the serene mountain setting by relaxing on the patio or enjoy all the dining, shopping and outdoor activity options located just minutes away. Bigger is not always better and this unique country cottage is a perfect getaway for travelers of all types.

Guest favourite
Home in Lebanon
4.97 out of 5 average rating, 117 reviews

The Nest on Mill

If your looking for a relaxing or adventure filled get-away in SW Virginia Mts, look no further than the Nest on Mill. “The Nest” is centrally-located and close to everything for those looking to explore Virginia's scenic attractions such as Tank Hollow Falls, Pinnacle Natural Area Preserve, Big Cedar Creek, St. Paul's Water & Spearhead Trails. With Abingdon and Bristol just around the bend, your getaway will be filled with great food, music, historical attractions. Start your engines!

Top guest favourite
Home in Kingsport
4.97 out of 5 average rating, 143 reviews

No Cleaning Fee, Cozy Cottage ; )

***NO CLEANING FEES!!!!!*** This sleek, modern, cozy cottage is centrally located in a safe neighborhood, perfect for both business and leisure stays. The space is designed with clean lines and contemporary furnishings, offering a comfortable and stylish retreat. It’s just a short distance from local hospitals, making it ideal for traveling nurses/professionals. *Holston Valley Med: 2.1 miles *Indian Path MC: 2.3 mi *Meadowview Convention:3.8 miles *Bristol Casino/racetrack: 21 miles

Top guest favourite
A spacious loft studio features an inviting seating area with a leather couch and coffee table. A ceiling fan provides airflow, while a well-equipped kitchen is visible in the background. A bedroom area is seen with two beds, surrounded by natural light from large windows.
Loft in Saint Paul
5 out of 5 average rating, 132 reviews

St. Paul: Roscoe's Retreat- Studio Loft Apartment

Roscoe's Retreat is a studio loft garage apartment that feels like home. There are steps leading to the second floor with roomy deck and private entrance. Sit on your deck and enjoys beautiful sunset views or stroll through our quaint town. This space has everything you need including a full kitchen, bedroom area, bathroom, Wi-Fi and washer & dryer. Bringing your 4 wheeler to enjoy the hundreds of miles of trails? No problem we have a single garage for off road parking of your ATV.

Top guest favourite
The exterior of a vintage Greyhound bus showcases a polished aluminum surface, reflecting its unique character. The bus is positioned on a gravel area, surrounded by lush greenery and open fields. Natural light highlights the bus's distinctive shape and retro design.
Bus in Abingdon
5 out of 5 average rating, 234 reviews

Retro Bus/Tiny House on Creeper Trail+Donkey Farm

Please read ENTIRE listing before booking. BAB (Big-Ass Bus) is a 1957 Greyhound bus on a donkey farm in SW Virginia. She's ON the Creeper Trail with all the amenities of a full-size home, but in a smaller package: hot+cold water; electricity; full kitchen with compact fridge; HEAT; A/C; HS WiFi; smart TV; +a cute little bathroom with toilet+shower. Perfect for 2 people (over 12 years old+under 6 feet tall). *No pets, please. One parking space.. NO CLEANING FEE.

Top guest favourite
The modern kitchen features white cabinetry and a large island with seating for four. Stainless steel appliances, including a refrigerator and range hood, complement the sleek countertops. Natural light fills the space through multiple windows, creating an inviting atmosphere.
Bungalow in Bristol
4.99 out of 5 average rating, 378 reviews

Bristol Bungalow w firepit & hot tub, 5 min to DT

This charming, renovated bungalow is ideally located minutes from historic downtown Bristol, VA/TN. Explore local dining, breweries, and shops, including Blackbird Bakery, all within a 6-minute drive. Enjoy easy access to the Bristol VA Casino (6 minutes) and the excitement of Bristol Motor Speedway (20 minutes). With convenient interstate access, this bungalow is the perfect base for exploring the region and creating lasting memories.

Top guest favourite
Home in Mendota
4.9 out of 5 average rating, 133 reviews

Cozy Cottage in The Wilderness

Escape the hustle and bustle of life in this quaint and cozy home in the mountains of Southwest Virginia. The property boasts breathtaking views of the Appalachian Mountains, a private pond, a fire pit and several outdoor activities to enjoy with the entire family. Enjoy your home away from home by unplugging and relaxing in the serenity of nature. We now have WiFi in the home as well for those who like to stay connected!

Top guest favourite
Loft in Saint Paul
4.96 out of 5 average rating, 104 reviews

Saint Paul Loft

Modern-style, private studio apartment located near downtown Saint Paul, VA. Perfect for a weekend away! Complete with a cozy bed, chaise loungers for reading and watching TV, along with a mini kitchen and breakfast area. Close to the entrance of Spearhead trails and the refreshing Clinch River, offering several opportunities for outdoor excursions. The loft is also within walking distance of several local restaurants.

Popular amenities for Castlewood holiday rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Russell County
  5. Castlewood