Holiday rentals in Castlewood

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Top-rated holiday rentals in Castlewood

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Top guest favourite
Cabin in Mendota
4.98 out of 5 average rating, 104 reviews

Cabin-Style Retreat/Firepit/Near trail

Welcome to The Cabin in Disguise, a private, thoughtfully remodeled home with rustic cabin-style finishes in the hills of Mendota. Relaxing getaways or family trips near Bristol. Enjoy a peaceful setting with covered porch seating, firepit with wood provided for evenings under the stars. Inside you will find fully equipped kitchen, coffee bar, comfortable gathering spaces, and everything needed for a relaxing stay. Near Mendota Trail, Carter Fold "Create Memories and be our guest"

Top guest favourite
A cozy sleeping area is framed by wooden walls, featuring a spacious bed adorned with soft bedding. A window opens to reveal stunning views of the mountains and greenery, while a chandelier provides ambient lighting. A small basket with items is placed on the bed.
Cabin in Lebanon
5.0 out of 5 average rating, 95 reviews

Mountaintop A-Frame cabin on Homestead

Mountaintop Sunrise & sunset views in the Appalachians. Elevation approx 2385 ft. Cabin Breazy, Our Glamping A-Frame, is a dry, primitive cabin with power located on a 35-acre Educational Homestead. We provide drinking water, electric burner, portable heater & AC, and mini-fridge. See additional notes & property information for bathroom details. Pets are welcome, contact for full pet policy. Please reach out with questions. View our other Clinch View Cabin with full-amenities on the property.

Top guest favourite
A friendly brown cow stands behind a wooden fence, accompanied by lush green fields in the background. A bright orange feeding container is mounted on the fence, contrasting with the earthy tones of the wooden posts. The scene is serene and agricultural, surrounded by trees.
Tiny home in Abingdon
4.99 out of 5 average rating, 461 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.

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, 159 reviews

The Ark at Zion Ranch

Nestled in the heart of 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
Cabin in Wise
4.94 out of 5 average rating, 99 reviews

Bear Creek Cabin • Vineyard Views & Fishing Pond

Escape to Bear Creek Cabin, overlooking the pond at MountainRose Vineyards. Enjoy peaceful porch views, modern comfort, and easy access to winery tastings, mountain trails, and quiet evenings under the stars. Perfect for couples, solo travelers, and small groups/families seeking a serene getaway. Fishing is allowed in the adjacent pond with a waiver signature. Must bring your own fishing equipment. Wine and charcuterie options can be pre-ordered to be waiting in the cabin for your arrival!

Guest favourite
A living area features a traditional brick fireplace surrounded by built-in shelves filled with books and decorative items. Light grey paneling adorns the walls, with a large artwork depicting a rural scene above the mantel, contributing to a tranquil ambiance.
Home in Lebanon
4.97 out of 5 average rating, 132 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
A newly constructed cottage sits against a backdrop of a vibrant sunset. A spacious porch with wooden railing is featured, along with an American flag softly waving in the breeze. Expansive windows reflect the warm glow of outdoor lighting, complementing the serene countryside views.
Cottage in Bristol
5.0 out of 5 average rating, 72 reviews

Shallow Creek Cottage

Newly constructed, this beautiful cottage is tucked away in the Appalachians, resting on 0.7 acres of peaceful countryside. Surrounded by rolling pastures and serene farm views, it offers the perfect blend of comfort and charm. Just 7 miles from the Hard Rock Casino and minutes away from downtown Bristol VA/TN, you’re close enough to enjoy the excitement—yet far enough away to unwind. With its cozy back porch and glowing sunset views, this home is a fresh take on quiet mountain living.

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 St. Paul
5.0 out of 5 average rating, 135 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
A cozy bedroom features a metal bed frame adorned with a plaid patterned comforter showcasing wildlife motifs. Matching side tables with lamps are positioned on either side. Natural light enters through a nearby window, complemented by warm wooden walls for a rustic feel.
Guest house in Elizabethton
5.0 out of 5 average rating, 148 reviews

Scenic, tranquil getaway, sleeps 4+

Relax at this peaceful place to stay. One bedroom plus comfy queen sofa sleeper and twin cot. Lots to do with the Appalachian Trail, waterfalls, 3 lakes, Roan Mountain, Cherokee National Forest, and Bristol Speedway and Casino nearby! Great fishing, hiking; ideal for adventure enthusiasts! In Stoney Creek on the outskirts of Elizabethton, Tennessee, you will have a complete kitchen, laundry, fire pit, internet tv, beautiful views and ample parking for a boat, camper or trailer.

Top guest favourite
A cozy living area is arranged with a plush sofa and loveseat featuring warm hues. A rustic wooden coffee table sits in the center, complemented by a braided rug below. Soft lighting is provided by a lamp beside the sofa, with curtains framing the windows.
Home in Abingdon
4.98 out of 5 average rating, 171 reviews

The Lamb's Ear

Enjoy a quiet country setting just 10 minutes from downtown Abingdon and the Virginia Creeper Trail, 20 minutes to the Appalachian Trail, 30 minutes to downtown Bristol. Enjoy pastoral views while you relax on the back deck, which runs the length of the house. The unit includes the entire main floor of the home with bedroom, bath, living room, full kitchen and laundry room. If you love the outdoors this is a great base for exploring this beautiful corner of the world.

Top guest favourite
A charming mountain home is set in a lush green landscape. A spacious lawn stretches out before it, while a deck can be seen extending from the side of the house. Tall trees and rolling hills rise in the background under a bright blue sky.
Home in Mendota
4.91 out of 5 average rating, 142 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
An inviting studio space features exposed brick walls and warm wooden floors. A cozy bed is positioned against the wall, while a turquoise chaise lounge offers a space for relaxation. Soft lighting from decorative string lights enhances the room's ambiance.
Loft in St. Paul
4.96 out of 5 average rating, 106 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