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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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Top guest favourite
Cabin in Mendota
4.98 out of 5 average rating, 101 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 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, 148 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
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, 454 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
Cabin in Wise
4.93 out of 5 average rating, 86 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 favourite
Cottage in Bristol
4.97 out of 5 average rating, 171 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 minutes to the Pinnacle and Bristol Regional Medical Center, 15 minutes to the Hard Rock casino and downtown Bristol, TN/VA. The house is over a 100 years old, but the interior 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 stay.

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, 155 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
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, 124 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 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, 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 newly constructed cabin sits among tall trees, featuring a spacious front porch with rocking chairs. The exterior is a muted green, with large windows inviting natural light. A gravel pathway leads to the entrance, bordered by fresh straw cover.
Cabin in Elizabethton
4.99 out of 5 average rating, 232 reviews

Hot Tub, Fire Pit, Ping-pong, Mt. View , & Privacy

Welcome to Stoney Creek Cabin! Enjoy a peaceful, private, and relaxing stay in our newly (2024) built cabin. We cut and milled the trees and built this cabin on our 50 acre farm and want you to enjoy it. It features a hot tub, ping-pong, foosball, porch swing, and firepit. Whether it is a family vacation or a romantic getaway this cabin will provide the opportunity to reconnect with the ones you love. 8mi to Elizabethton, 16mi to Johnson City and Bristol. Book your stay today!

Top guest favourite
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.

Guest favourite
Dome in Todd
4.94 out of 5 average rating, 237 reviews

Tiny Treepod - Hot Tub, Views, Romantic Oasis

The newest of the Tiny Escapes properties, the Tiny Treepod offers a unique and upscale experience for the nature loving adventurer. Have it both ways with a retreat in nature AND a 10 minute drive to historic downtown West Jefferson or quaint Todd or 25 minutes to Boone. Enjoy the well appointed custom dome with hot tub, fire tables, grill, hanging chairs, dining nook, and comfy outdoor furniture. Relax and refresh while experiencing the joy of tiny living!

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, 139 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!

Popular amenities for Castlewood holiday rentals

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