Vacation rentals in Castlewood

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Top-rated vacation rentals in Castlewood

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Guest favorite

Cabin in Rogersville

4.98 out of 5 average rating, 362 reviews

Cozy Country Log Cabin!

Cozy log cabin on quiet 22+ wooded acres with creek and well stocked pond! Enjoy all the comforts of home in a rural, peaceful setting. Seasonal Babbling brook, covered porch, fire pit , picnic & BBQ pavilion, and hiking trails! Bring your hiking Boots ! Located just 11 miles from Rogersville (the second oldest city in Tennessee, founded by Davie Crocket's maternal grandparents!). Located 12 miles from Crockett Springs Park and Historic Site. Public boat launch located at Clinch River nearby.

Guest favorite

Cabin in Shady Valley

4.97 out of 5 average rating, 436 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

Cottage in Abingdon

4.98 out of 5 average rating, 326 reviews

The Olde Springhouse - Downtown, Abingdon

The Olde Springhouse is our cozy cottage just 1 block off Main str and a few more from the Virginia Creeper Trail-Head. The Trail is open 17 from Abingdon to Damascus! This gem is at the epicenter of shops, restaurants and nightlife! Enjoy all our town offers within walking distance- The Barter Theatre, The Creeper Trail, The Tavern, Jack's 128 Pecan, Foresta, Summers Rooftop/Cellar, Rain, The Girl & The Raven, SweetBay Brewery, and much, much more- and it was literally built over a spring!

Guest favorite

Guesthouse in Abingdon

5 out of 5 average rating, 164 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.

Guest favorite

Tiny home in Abingdon

4.98 out of 5 average rating, 272 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 favorite

Home in Elkhorn City

4.84 out of 5 average rating, 218 reviews

The Alma Potter House

Family friendly, small fenced in area. Two bedrooms/bath upstairs, 2 bedrooms/bath downstairs. large living/dining room. Rural, white water rafting, near Breaks Interstate Park, Pine Mountain Trail, Hillbilly Days, Hatfields & McCoys. Be in Norton/Wise, Grundy, VA, Pikeville, KY or Williamson WV in minutes. FB pages: Breaks Interstate Park, City of Elkhorn City Events, Southern Gap Adventure Trails, Arts Collaborative Theatre Inc., Kentucky Whitewater Rafting. Pike Co Tourism webpage.

Guest favorite

Tiny home in Blountville

4.95 out of 5 average rating, 112 reviews

“The Genesis” - Luxury Tiny Home at Zion Ranch

Nestled in the heart of a 35 acre ranch in East Tennessee you will find lively chickens and ample forest. This modern tiny home offers all the essentials for a comfortable stay. Featuring a wrap-around deck with a large walk out glass slider. You'll find everything you need for a relaxing visit, including a fully equipped kitchen, luxury queen bed and two twin XL’s in the loft, and washer & dryer. The minimalist design makes this an ideal getaway for those seeking peace and simplicity.

Guest favorite

Chalet in Kingsport

4.97 out of 5 average rating, 507 reviews

The Bearfoot Chalet Kingsport, TN

Our Mountain Chalet is the Perfect GETAWAY. Best location to stay in our ENTIRE Area. We are in the City limits of Kingsport, 3 miles from downtown. A DOG MUST BE PRE-APPROVED and there will be an additional pet fee. I do not charge a cleaning fee as long as guest leave place clean as found. Charter cable TV and WIFI access provided. Also located on our 6 acre estate is another BNB rental the "BEARFOOT RETREAT" , a 3BR house should a larger group want to stay close together.

Guest favorite

Loft in Saint Paul

5 out of 5 average rating, 114 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, 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.

Guest favorite

Home in Whitesburg

4.98 out of 5 average rating, 478 reviews

Cowan Creek Cottage

Cowan Creek Cottage is close to the Cowan Community Center and only 5½ miles outside the city limits of Whitesburg. The cottage is located at the foothills of Pine Mountain. You’ll love the cottage and enjoy the feel of having your own little home in the mountains. Enjoy a clean and comfortable home away from home while visiting friends and family and enjoying our community. Cowan Creek Cottage is good for couples, solo adventurers, business travelers, and families.

Guest favorite

Cottage in Glade Spring

5 out of 5 average rating, 163 reviews

The Cottage Around the Corner

Right around the corner or right on the way, the Cottage Around the Corner is convenient for travelers. Whether visiting the beautiful mountains to bike or hike the Creeper Trail, sightseeing in the historical Abingdon or Bristol area, attending a game at E&H or just passing through to another destination, our goal is to provide a warm and welcoming home for your getaway. Resting on an acre of land and right off I 81 enjoy your stay in our cozy, country cottage.

Guest favorite

Cottage in Nickelsville

4.99 out of 5 average rating, 139 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.