Vacation rentals in Castlewood

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Top-rated vacation rentals in Castlewood

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Top guest favorite

A modern kitchen with light wood flooring and green walls is illuminated by recessed lighting. A wooden dining table is surrounded by six chairs, and a patterned rug rests beneath it. The kitchen cabinetry is stylish, with appliances and open shelving visible in the background.

Home in Kingsport

5 out of 5 average rating, 163 reviews

Little Red House on the corner

This stylish place to stay has recently been fully renovated, fully furnished with all the necessities, 2 Bedroom, 2 full baths. The Couch can be converted into an additional bed, allowing for for 6 guests. Open and inviting space w/ 10' Ceilings . There are smart TVs in both bedrooms, living and dining room. Kitchen has Induction Stove, dishwasher, microwave, plates, glasses, silverware, pots, pans and much more. Complimentary Coffee, bathroom supplies - toothpaste, toothbrush ,soap and shampoo

Guest favorite

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, 479 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.

Guest favorite

The exterior of the duplex unit is depicted, featuring a light brown siding and a large front porch with wooden steps. Two windows are visible, allowing natural light into the home. A green trash bin is placed next to the porch, and a well-maintained lawn is shown in the foreground.

Apartment in Bristol

4.94 out of 5 average rating, 227 reviews

Central Bristol Comfort Hideout

Feel right at home in this centrally located and freshly remodeled private duplex unit. You have the entire space to yourself, surrounded by quiet neighbors who are mostly long term residents. This unit offers it all! It comes with everything you to need to feel like home. The property is located just 1.5 miles from I-81, 1 mile from the Hard Rock Bristol Casino, a couple of minutes drive to downtown (State Street), walking distance to the Mendota Trail, and 8.5 miles to Bristol Motor Speedway.

Top guest favorite

A quaint cottage is surrounded by lush greenery, featuring a metal roof and an inviting garden with colorful flowers. A picnic table sits on a stone pathway leading to the front door, enhancing the outdoor space.

Guesthouse in Damascus

4.96 out of 5 average rating, 1,401 reviews

Ruby's Rest

NO CLEANING FEES. NO TO DO LISTS BEFORE CHECKING OUT. NO PET FEES. Cozy, private one room cottage (with bathroom), run by a loving, easy-going, non-judging family. Cottage measures 12' x 24' (total of 288sq. feet). Very relaxed environment. Flat rate of $50.00. UPDATE: Deck is now enclosed with old window panes. Super cozy. Has a sink with hot/old water, a hot plate, large toaster oven, and utensils. I am am still putting finishing touches on it, but available for use. Pictures soon.

Top guest favorite

A single-story entrance is framed by a neatly manicured lawn. A light green exterior wall features a white door and window, adorned with decorative shutters. Potted plants line the pathway, adding a touch of greenery, while a colorful welcome mat invites visitors.

Guesthouse in Abingdon

5 out of 5 average rating, 227 reviews

Cozy & Private "The Little Green Pig" Abingdon

Cozy space for a getaway!. Located a block off Main Street and walking distance of Historic Downtown Abingdon. We strive to make your stay special. The apartment has upgraded wifi, work space for your tablet, or device. Roku tv, full-size kitchen, and private bedroom with queen bed . Sofa bed suitable for two children, or, one adult. The backyard patio includes a play house for children with swings, slide, and zip line. Creeper Trail access from stay via the Abingdon Urban Pathway.

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, 214 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, 346 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

A welcoming porch is featured at the entrance, showcasing a wooden railing and two black chairs. A simple wreath adorns the door, complemented by greenery and shrubs surrounding the area. The bright exterior is accentuated by clear blue skies.

Guest suite in Blountville

4.98 out of 5 average rating, 137 reviews

A Tiny Retreat near Tri-Cities

This Tiny Retreat is near everything, making it easy to plan your visit. One mile away from Tri-Cities Airport and a short drive to Bristol, Johnson City, & Kingsport. You’ll love having your own space in the scenic country area, while still being centrally located near all the things the area has to offer: Bristol Motor Speedway, Hard Rock & Bristol Casino, ETSU, Eastman, Boone Lake, South Holston River & more. Checkout “T&S’s Guidebook - East Tennessee” for our local recommendations!

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

4.71 out of 5 average rating, 119 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 Saint Paul

5 out of 5 average rating, 126 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

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, 148 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.

Top guest favorite

A serene river scene displays individuals floating on tubes, surrounded by lush greenery. In another view, a bright bedroom features a spacious bed adorned with a colorful quilt. A gentle waterfall cascades over rocks, while a wooden bridge extends into a vibrant natural setting.

Guesthouse in Mendota

4.99 out of 5 average rating, 187 reviews

RiverCliff Cottage

Escape to RiverCliff Cottage! Come relax at RiverCliff Cottage-a charming detached unit with its own private entrance. This cozy retreat is perfect for 2 adults looking to unwind and reconnect. Note: #1. This is a no smoking property; #2. Pets are not allowed, however, guests should feel comfortable with our dogs roaming the property; #3. Guests should feel comfortable with steps as this is a 2nd floor unit. See photos to view the steps.