Holiday rentals in Dickenson County

Cozy Mountain Cottage Overlooking Golf Course

Slow down with the whole family in true Southern fashion at our cozy country cottage located in a rural mountain community. This three bedroom, two bath home overlooks Willowbrook public golf course and is just mintues from Breaks Interstate Park, home of "the Grand Canyon of the South." Local attractions include hiking and ATV trails, kayaking/white water rafting, ziplining, water park, picnic shelters, playgrounds & more! Winter guests are likely to encounter majestic views of wild elk grazing

Hit the Breaks Cabin - Ideal Location with a View!

Welcome to "Hit the Breaks Cabin" - the perfect getaway for outdoor enthusiasts! Located just one mile from Breaks Interstate Park, this three bedroom cabin offers endless outdoor activities to explore. Spend your days hiking, kayaking, or riding ATVs, and your nights soaking in the hot tub or roasting marshmallows under the stars. Enjoy your morning coffee with breathtaking views of the golf course and surrounding mountains. Book now and indulge in the perfect blend of adventure and relaxation!

2BR/1BA Private Suite near Breaks & Flannagan Dam

Located Near John W. Flannagan Dam - Haysi, Breaks, & Vansant VA Enjoy a private guest suite with up to 2 private bedrooms, private entrance and full bathroom; no shared spaces with the host owner or other guests; your reservation only. Pricing is based on number in your party. The base rate includes 1 bedroom for 2 people allowing solo travelers or 1 couple a lower rate while families or travelling friends can share a deluxe suite of up to 4 people total on double occupancy with 2 bedrooms.

Russell Fork River Lofts

Relax with the whole family at this peaceful and beautiful loft. If you are looking to explore the Breaks Interstate Park and the Crooked Road we would love to have you stay at our new renovated loft. This top floor loft features 1 bedroom with a queen bed and a queen sofa bed. A full kitchen and bathroom with shower tub combo with washer and dryer. The loft is 8 miles from the Breaks Interstate Park and is directly on the spearhead trail. Plenty of parking for all your vehicles and trailers.

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!

Charming 5BR Near Breaks < 10 min

Welcome the "The Holly House." This mid century modern home has been upgraded with your comfort in mind. Whether you're enjoying a quiet moment outside, gathered with friends and family in the living room, or enjoying a movie in the game room there is something here for everyone. We are conveniently located near the Breaks Interstate Park. Simply take a 5 minute drive to access hiking trails, kayaking, live theatre, a water park, horse back riding, rock climbing, fishing and zip lining.

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.

Bowling Rentals - Pine Fork Lodging

Looking for the perfect place to stay near the Hillbilly Trails? You can’t get any closer. Located approximately .2 miles from trail 64 entrance, this home offers direct access without ever getting on the main road—you’re literally right there. This beautiful home sleeps up to 8 guests comfortably and offers ample parking for trucks and trailers, making it ideal for riders, families, or groups. No pets allowed. 201 Pine Fork Lodging offers comfort, space, and unbeatable trail access.

The Alma Potter House

Family friendly, small fenced in area. 2 BR/bath upstairs, 2 BR/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: Breaks Interstate Park, Hillbilly Trail System, City of Elkhorn City Events, Southern Gap Adventure Trails, Arts Collaborative Theatre Inc., KY Whitewater Rafting. Pike Co Tourism webpage.

Haysi Nature Getaway w/ Fire Pit & On-Site Creek!

The ultimate nature getaway awaits when you book this charming Haysi vacation rental! This secluded 4-bedroom, 1-bath house is perfect for any group of outdoor enthusiasts looking to disconnect and unwind in a truly relaxing environment. Take advantage of the on-site Lick Creek and test your fishing skills, spot deer or other local wildlife from the home’s private fire pit, or head out to explore nearby sights, like Breaks Interstate Park or the Ralph Stanley Museum, during your stay!

Hillbilly Holler Lodging - Bobby's Bungalow

Newly renovated cabin for any UTV enthusiast, located just 30 seconds from the Hillbilly Trails entrance (trails 20 & 142) and 5 minutes from a gas station. No need to trailer your UTV! Sleeps up to 6 with 4 twin beds and a queen pull out couch. Full kitchen, washer and dryer, and 2 full baths are also included. We have another brand-new Airbnb cabin on the property, Dixies Den, that sleeps 4 so we can accommodate large groups.

Newly restored home prime location in town

Located in town, within walking distance to the grocery store, convenient stores, restaurants, boutiques, and next door to The Well coffee shop/bakery. Relax on the expansive porch with your coffee or if you're looking for entertainment, the Ralph Stanley Museum and The Jettie Baker center are just up the street. Only a short drive to the Breaks interstate park, birch knob tower & John Flanagan Lake.