Vacation rentals in Castlewood

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Top-rated vacation rentals in Castlewood

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

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Top guest favorite
Home in Elizabethton
5.0 out of 5 average rating, 118 reviews

REELaxed on Watauga River, Fishing, Family Fun!

Welcome to REELaxed on Watauga River 🎣 Walk straight out your back door and fish anytime—no driving, no crowds. With over 1200 feet of private river frontage, nestled in the city of Elizabethton, this is one of the most unique locations. Recently renovated and designed for comfort, our home gives you the perfect mix of relaxation and adventure. Whether you’re casting a line, enjoying the fire pit, or just taking in the river views, you’ll feel completely REELaxed from the moment you arrive.

Guest favorite
A small rustic cabin is situated along a riverbank, surrounded by lush greenery and mature trees. A winding driveway leads to the cabin, which has a red roof. The serene river is visible alongside the property, reflecting the surrounding natural landscape.
Cottage in Mendota
4.92 out of 5 average rating, 62 reviews

Cozy riverfront cabin on 106 acres near Bristol

Relax with family or friends at this peaceful cabin. This is a small rustic 2 bed 1 bath riverfront cabin with over a mile of frontage on the North Fork Holston River. Bring tubes, fishing poles, hiking boots, and marshmellows. This cabin is secluded and truly puts you in the heart of nature. Birds, fireflies, deer, turtles, otters and others with the sounds of the river right next to the cabin. This is an active cattlefarm. 45 minutes from Bristol Motor Speedway. No smoking or vaping indoors.

Top guest favorite
The exterior of a uniquely designed house is showcased, featuring a mix of wood and stone materials. The property is set on a spacious lawn with trees in the background, and large windows provide an airy feel, allowing natural light to filter indoors.
Home in Bristol
4.98 out of 5 average rating, 265 reviews

Unique Custom Built Home with Hot Tub & Pool Table

Welcome to "The Bristol Royale" and thank you for your interest in our property. We have spent the past few months carefully decorating and updating this beautiful place. We offer fast Wi-Fi, 3 big screen Roku TV's , coffee bar, King suite, 2 queen bedrooms, one bedroom that sleeps 4 and one private bedroom downstairs. You can enjoy playing pool, ping pong, cornhole and an assortment of other games plus relax in the hot tub and read a book at the fire pit table. Fire up the Blackstone too.

Top guest favorite
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, 475 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 favorite
Cabin in Wise
4.93 out of 5 average rating, 102 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!

Top guest favorite
Cottage in Bristol
4.97 out of 5 average rating, 186 reviews

Cutest little farmhouse in Bristol.

Relax in total comfort at this lovely, private farm house. We are located right off of 11W close to I81. 7 min to the Pinnacle and Bristol Medical Center, 15 min to Hard Rock and downtown Bristol, TN/VA. The house is over a 100 years old, but the remodel has all the modern conveniences you need to make yourself at home while you enjoy all Bristol has to offer! All the privacy you could want, a large yard, and a fire pit add to the enjoyment of your visit. And no cleaning up after your stay!

Top guest favorite
A rustic cabin is nestled among trees on a grassy hillside. The front porch features a wooden railing, offering a shaded retreat. Surrounding foliage includes evergreens and patches of orange pine needles, creating a natural landscape that enhances the serene setting.
Cottage in Abingdon
4.92 out of 5 average rating, 73 reviews

Bob's Bridge

Welcome to Bob’s Bridge, our Hidden Valley Hideaway. We hope you’ll enjoy sitting on the front porch with a cup of coffee in the morning and watching the mist rise up from the stream the bridge crosses. Don’t be surprised if you see a flock of turkeys or a handful of deer wandering around. They appreciate the stone bridges and walls built by hand by Bob, who loved all nature. Bob’s Bridge is intimate and rustic, and we hope that’s what you were looking for when you decided to stay here.

Guest favorite
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, 133 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!

Guest favorite
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
4.75 out of 5 average rating, 161 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.

Top guest favorite
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, 138 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 favorite
Cabin in Mendota
4.98 out of 5 average rating, 105 reviews

Fall Hawks, Fire Pit Cabin- Style Retreat

🦅🦅 Fall comes alive in Mendota, the “Hawk Capital of the World,” as migrating hawks soar above Clinch Mountain. Come home to The Cabin in Disguise, a peaceful, spotless retreat filled with rustic charm and comfort. Sip coffee from your cozy coffee station on your covered porch, enjoy your spacious yard, then gather around the fire pit as evening settles in. Feel the mountain breeze, breathe deep, slow down, and make memories in your little mountain hide away.

Top guest favorite
A newly remodeled cottage is displayed with a light green exterior and a welcoming front porch. A wooden deck features two chairs and potted plants, while the surrounding grassy area complements the serene country setting. The roof is covered in metal sheeting, adding to the rustic charm.
Cottage in Nickelsville
4.99 out of 5 average rating, 152 reviews

Happy Trails Cottage Guest House

Newly remodeled cottage located in serene country neighborhood within 30-40 minutes of Devils Bathtub, Carter Fold, Natural Tunnel State Park, Spearhead Trails, Scott Co Horse Park, Clinch and Holston Rivers, Mendota Fire Tower. Within an hour of Bristol Motor Speedway. Sip your morning coffee on the back porch while watching Charolais cattle graze. Commune with nature and feel the stress slip away. Enjoy the run of the house! Morning coffee is provided.

Popular amenities for Castlewood vacation rentals