Vacation rentals in Castlewood

Ivy's Cottage in Abingdon, VA, 2 br, 1 ba

Located on a third-generation cattle farm, Ivy’s Cottage sits in Abingdon, VA just minutes from downtown and the Creeper Trail. Take in scenic farm views from this cozy 2 br, 1 ba retreat. The main bedroom features a queen bed in an open-concept layout connected to the living space. The upstairs loft offers two twin mattresses, perfect for extra guests. A spacious kitchen is stocked with pots, pans, utensils, salt/pepper, a dishwasher, and fridge — everything you’ll need for a comfortable stay.

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.

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!

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.

Mountaintop Glamping A-Frame w/ Scenic Farm Views

Cabin Breazy is a unique A-frame at Breath of Dawn, a 35-acre educational homestead & immersive mountain destination in Southwest Virginia. Best enjoyed over 2-3 nights, your stay includes sweeping sunrise & sunset views, peaceful surroundings, and opportunities to personalize your visit with seasonal farm experiences. This dry cabin includes power, drinking water, a mini-fridge, electric burner, heating, A/C, and is pet friendly(request pet policy). See additional notes for bathroom details.

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.

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!

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!

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!

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.

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.

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.