Vacation rentals in Ashland

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Top-rated vacation rentals in Ashland

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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, 477 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.

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 rustic cabin is nestled among vibrant autumn foliage, with a mix of yellow, orange, and green leaves surrounding it. The structure features a sloped metal roof and open porch, blending harmoniously into the natural landscape. Tall trees provide a serene backdrop against a clear blue sky.

Barn in Laurel Bloomery

4.97 out of 5 average rating, 199 reviews

Near Damascus CABIN overlooking lovely Horse Farm

Let your heart rejuvenate while listening to the creek and soaking in the beauty of the horse farm. This newly finished upstairs loft/cabin is part of an old historic barn built in the 1800s and used as one of the first Pony Express! Uniquely decorated with large windows and a great view of the pastures and distant mountains, your sanctuary is only 6 miles to Damascus, VA, 45 min. to Boone, NC, and 25 min. to Abingdon, VA. Enjoy the Cherokee National Forest trail leading to a double waterfall!

Top guest favorite

The living area features a cozy blue sofa adorned with various cushions. A rustic coffee table occupies the center, with a guitar displayed on the wall above. Light from the windows enhances the warm wood tones of the ceiling and walls.

Tiny home in Warrensville

5 out of 5 average rating, 123 reviews

stylish modern cabin with panoramic views

Relax & recharge at this newly renovated log cabin with gorgeous wraparound views. Dine on the covered deck, sip wine at the firepit, listen to smooth jazz on bluetooth and sleep like a baby in the luxurious bedding. Stunning in every season! Mountaintop location w private drive. Fully stocked kitchen. 55" TV w Netflix, Hulu & more. FWD recommended in winter. Explore nearby wineries, hiking trails and kayak the New River. 15 min to shops & restaurants in charming downtown West Jefferson.

Top guest favorite

A rustic log cabin with a green metal roof is nestled among trees, showcasing a front porch with a star decoration above the door. A gravel pathway leads to the cabin, bordered by lush greenery and ornamental plants.

Cabin in Creston

5 out of 5 average rating, 137 reviews

A DREAM BY THE STREAM* private 10 ac-Dog Friendly!

A Dream by the Stream is a very private and rustic 2 Br/2Ba log cabin overlooking a bold stream on 10 beautiful and remote acres with walking trails, a pond with dock, campfire pit, and amazing garden stonescapes. Our 750 sq ft. Cabin offers WiFi, streaming TV, central AC and heat, fully stocked kitchen, coffee provided, towels, comfortable bed and quality linens. We are 1/2 mile from the North Fork of New River. It's a perfect spot to relax, unwind, and enjoy the mountains. Dogs welcome.

Top guest favorite

A cozy bedroom features a spacious bed with a neutral quilt and decorative pillows. A bedside table with a lamp provides soft lighting. Natural light enters through two windows, partially covered by light curtains, creating a bright and calming atmosphere.

Guesthouse in West Jefferson

4.98 out of 5 average rating, 208 reviews

Mountain escape great views!

Leave the world behind in your private guest house. Fully stocked kitchen, living room, bedroom with two beds and bathroom with walk in shower. Enjoy great mountain views on private deck. Downtown West Jefferson, a short 4.5 mile drive, is a vibrant small town with shops, breweries, restaurants and much more. Kayak the new river, hike Mount Jefferson, drive the Blue Ridge Parkway. Enjoy cool mountain breezes in summer, beautiful fall foliage and winter sports close by. Adventure awaits!

Guest favorite

The interior of the tiny house features wooden walls and a cozy layout. A full-size bed with a red coverlet is positioned next to a window. A kitchenette with dark countertops includes a sink, a toaster oven, and a kettle, while natural light filters through the nearby windows.

Tiny home in Warrensville

4.97 out of 5 average rating, 258 reviews

The Hobbit House

The Hobbit House is a tiny house (15x11'); Full size bed, futon/couch, outdoor tub, shower, electric fireplace, patio, picnic table, fire ring, and outhouse with composting toilet. The patio overlooks a pond and is part of a 53 acre forested property in the Blue Ridge. WiFi is now included. Glamp in style! The main lodge is just up the driveway if you need to contact the host. The outdoor shower/tub is NOT fully enclosed or private, and may be turned off in a freeze. Nature lovers only!

Top guest favorite

A comfortable living area features a spacious leather sofa adorned with decorative pillows. A wooden coffee table sits in front, and a wall-mounted television offers entertainment options. Natural light filters through the window, while a gas fireplace adds warmth to the space.

Condo in West Jefferson

4.95 out of 5 average rating, 197 reviews

Cozy 2BR, Pet-OK, Mountain Views, close to DT

Entirely renovated, this darling duplex overlooks the meadow with stunning mountain views. Located 5 min to charming downtown West Jefferson. This vacation spot has so much to offer! With its location, you can enjoy outdoor activities such as hiking, canoeing, kayaking, and fishing along the New River, nature walks and biking along the Blue Ridge PKWY. This unit is stocked with many convenient amenities and also offers an area for outdoor dining with a charcoal grill and an open fire pit.

Top guest favorite

A charming guest house is depicted, set against a backdrop of trees showcasing autumn foliage. The exterior features a green metal roof and white siding, with large windows allowing natural light. A picnic table is positioned on the grassy area, enhancing the outdoor space.

Guesthouse in Creston

4.95 out of 5 average rating, 124 reviews

Boaz Brook Farm Guest House

If 24/7 entertainment is what you are looking for, continue your search. If serenity, peace, and enjoyment of mountain beauty is your wish, you have hit the jackpot! Don't worry, we have electricity, running water, and fiber optic WiFi. We feature a two-story, separate guest house in beautiful surroundings with a master suite upstairs including a queen bed, reading corner, TV area, and full bath. Downstairs you will find a kitchen, small bedroom, and a half-bath.

Guest favorite

A spacious guest suite features a large bed with white linens, framed by two windows dressed in dark curtains. A wooden dresser and a seating area with a chair are included. A coffee station is visible for convenience, enhancing a relaxing atmosphere.

Home in West Jefferson

4.99 out of 5 average rating, 131 reviews

Spacious suite, private entrance & bath, deck!

Welcome to your private suite at Soul Fire Camp + Cabins! Enjoy your spacious private suite with a large luxury bathroom, private entrance, and covered porch. The suite offers a unique and cost effective alternative to a hotel stay, with all the amenities. The price is for 2 guests and to add a 3rd, we charge +$15. This is so you don’t pay extra if not needed. Check out all of our listings at: www.airbnb.com/p/soulfirecampandcabins

Top guest favorite

A farmhouse-style cottage is presented with a white exterior and a metal roof. A covered porch with white railings lines the front. Surrounding greenery and gravel pathways complement the serene setting, while the sun creates a bright backdrop, enhancing the peaceful atmosphere.

Cottage in Creston

4.99 out of 5 average rating, 183 reviews

The Cottage at Historic Sutherland Manor est. 1807

Helene update: the farm is undamaged and roads leading to it are passable. This farm cottage is located on a historic 40 acre farmstead behind a beautiful farmhouse (which is under renovation) with views of The Peak, Ashe County’s highest mountain. We are bordering Elk Knob State Park and a 10 minute drive to the park entrance. The farm is located in the historic Sutherland valley district and was built in 1807 by Thomas Sutherland.

Guest favorite

A rustic cabin is framed by lush greenery, with a warm wood exterior and a striking red roof. A large covered porch extends across the front, supported by wooden posts, and a set of steps leads up to the entrance.

Cabin in Mouth of Wilson

4.9 out of 5 average rating, 341 reviews

Briar Run Cabin near Grayson Highlands Park

Explore the creek, relax in the sauna, and enjoy the privacy of a secluded, two-acre tract adjoining the Jefferson National Forest, near Grayson Highlands’ wild ponies and White Top’s famed Creeper Trail. Bring your slingshots, sit on boulders, and warm yourself by one of two natural-stone fire pits. Help yourself to Starlink Wi-Fi and Roku to stream your favorite shows. This is one of the most untouched areas in America.