Vacation rentals in Simmons Gap

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Top-rated vacation rentals in Simmons Gap

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Guest favorite

A modern house is nestled within a lush forest, partially hidden by tall trees. Large glass windows reflect the surrounding greenery, while a spacious deck extends from the structure, offering a view of the forest floor. The entrance is accessed via a gravel pathway.

Home in Dyke

4.97 out of 5 average rating, 127 reviews

Moss Vineyards Lodging

We welcome you to our new modern house (2020) located on 52 private wooded acres, adjacent to our winery and the Blue Ridge. Designed and built by award winning Architect and wine maker, Barry Moss, it is gorgeous inside and out. Decks overlook the river, forest and mountain farms. A path leads down to the river beach. Walk up to the top of the mountain and experience the best wines and views of any winery in Virginia. Modern interiors with wood floors, granite counters, and tiled bathroom.

Guest favorite

A spacious family area features comfortable seating, including a floral-patterned sofa and two armchairs in vibrant colors. A large area rug anchors the space, and light enters through multiple windows. A ceiling fan contributes to a relaxed environment.

Apartment in Elkton

4.96 out of 5 average rating, 252 reviews

Awesome View

Awesome View is appropriately named; we have nearly a 360 degree view of mountains—Blue Ridge and Massanutten. You have the advantage of a fully equipped kitchen, a dining nook with a view of the mountains, full private bath, 12x12 bedroom, spacious family area, cable, wifi, washer/dryer and private parking within inches of your door. We have furnished games, puzzles, reading materials for your spare moments and relaxing pleasure. We ask that you bring no pets and no smoking, vaping or drugs.

Guest favorite

The cabin exterior is set against a backdrop of trees with fall foliage. A spacious deck extends from the front, featuring wooden railings and a large central window. Natural stone accents the base, blending the structure with the surrounding landscape.

Cabin in Stanardsville

4.97 out of 5 average rating, 123 reviews

Whippoorwill Way Cabin with Mountain Views

5 star host of Rabbit Hollow cabin, presents this completely renovated mountain cabin, secluded retreat for couples or families. Walking distance to Shenandoah National Park, spectacular mountain views from spacious deck. State of the art kitchen , granite counter tops, master suite with king bed, and bathroom with charming mural. Warm up by wood burning stove. Lower level holds second bedroom with brand new queen bed, bathroom and living area with trundle bed sleeps two and electric fireplace.

Guest favorite

A charming cottage exterior showcases a green facade with textured wood siding, complemented by a welcoming porch. Outdoor seating is provided by rustic chairs around a fire pit on the lawn. A table nearby offers an inviting spot for dining, set against a backdrop of distant mountains.

Cottage in Crozet

4.91 out of 5 average rating, 191 reviews

Idyllic Cottage Retreat

⭐️ Condé Nast Traveler Approved ⭐️ Cozy cottage nestled on a historic 400-acre Blue Ridge Mountain farm abutting Shenandoah National Park. Every space inside this cozy cottage is creatively styled, with tons of perfectly imperfect charm. Outside, a hammock beneath the elm trees, fire pit and grill, all allow for enjoying the splendor of this peaceful enclave. Excellent day-tripping to many of central Virginia's celebrated wineries and breweries, as well as scenic drives and hiking trails.

Top guest favorite

A spacious, two-story house with white siding and large porches is featured. Lush green grass surrounds the structure, and the landscape includes open pastures and trees. The setting is serene, with plenty of natural light illuminating the exterior.

Home in Dyke

4.96 out of 5 average rating, 318 reviews

Living Water Farm, Blue Ridge

Iconic home and Farm in Dyke, Virginia, circa 1891. Situated on the Roach River with views of the Blue Ridge mountains and pastures. Relax on one of the double porches or under on of the shade trees. The stone fireplace warms the heart and soul on a cool evening. Minutes from the Shenandoah National Parkway, the Blue Ridge School and several beautiful wineries. Approx. 12 miles from CHO airport, 20 min from Blue ridge Parkway, 10 min. to Standardsville and 20 miles to Charlottesville.

Top guest favorite

A covered porch extends from the cabin, furnished with rocking chairs. The expansive green landscape is framed by rolling hills under a cloudy sky, with the sun peeking through the clouds, creating a serene outdoor space for relaxation.

Cabin in Elkton

4.96 out of 5 average rating, 166 reviews

Mountain View Cabin

Take it easy at this unique getaway in the beautiful Appalachian Mountains. Our cabin provides you with a peaceful stay and a once in a lifetime experience. It sits on privately owned land with 96 acres of farm, hills, and mountains. You can enjoy your morning coffee on our covered porch while watching the cows graze. Our cabin is within 10 miles of the area’s popular attractions: Shenandoah National Park & Massanutten Resort. We have everything you need for a memorable stay in the Valley.

Guest favorite

The dark wooden cabin, framed by lush greenery, sits at a hillside location with panoramic mountain views. A deck extends from the cabin, featuring a hanging basket chair. A warm sunset casts a golden hue across the sky, enhancing the serene atmosphere.

Cabin in Free Union

4.99 out of 5 average rating, 165 reviews

Shenandoah Stargazer with Sauna

Stargazer is the perfect place to get away from it all! The stillness and serenity of being nestled in a bird and wildlife sanctuary is so good for your soul. Watch the sunrise from a hanging basket chair at 2700 feet of elevation, or wait for moonrise and toast spectacular star views! Relax in the sauna after a day filled with hiking and an al fresco meal on the deck. Roast s’mores at the deck fire table or over the side yard fire pit. There's magic in the air at this mountaintop retreat!

Top guest favorite

An open-concept living area features wood-paneled walls and high ceilings. Natural light floods through multiple windows, illuminating comfortable seating arrangements. A spiral staircase is visible in the background, while a dining table and colorful area rug add to the cozy ambiance.

Cabin in Elkton

4.97 out of 5 average rating, 145 reviews

One-of-a-kind cabin, hot-tub, near National Park

This is a year-round, stunning creekside oasis on 6 acres bordering the Shenandoah National Park & traversed by Hawksbill creek. Luxury & design meet chalet-style charm. This cabin is unlike any other! In summer, enjoy tubing on the Shenandoah river, hiking SNP, or wandering the 6-acre property bordering parkland. Visit the quaint town of Elkton and its wineries, breweries & antique stores. Experience nearby Massanutten Resort with its skiing, adventure park, etc. If you know, you know!

Guest favorite

A quaint cottage is nestled in a lush green landscape, surrounded by colorful autumn trees. Rolling hills and the distant Blue Ridge Mountains form a scenic backdrop, with a clear sky above and soft sunlight illuminating the scene.

Tiny home in Free Union

4.95 out of 5 average rating, 125 reviews

Little Forest Tiny Cottages in Free Union

Enjoy the breathtaking views of the Blue Ridge Mountains on this 26 acre Olde English Babydoll Sheep farm right from your window. Our farm is a haven of peace and serenity in a secluded but centrally located area just 18 miles northwest of Charlottesville. Wake up to delicious farm fresh breakfast from our eco-friendly farm. Take pictures of fluffy sheep and angora rabbits grazing on rolling hills. Hike our private trail. Breathe in the fresh mountain airs. Sleep in. Slow down. Relax.

Superhost

The cabin is situated amidst rolling hills, presenting an unobstructed view of the surrounding mountains. A grassy area encircles the home, with scattered trees in the foreground. The clear blue sky enhances the serene atmosphere of the elevated location.

Cabin in Free Union

4.95 out of 5 average rating, 170 reviews

Fall Foliage Awaits! Views Firepit 9/19-9/20 Open!

Fall in love with this cabin through one of the most awe-inspiring sites in the US: an endless blue-green mountain majesty. With unimpeded views of the Blue Ridge Mountains from 3300 feet of elevation, you'll be able to escape from any daily stresses. The fall foliage provides a wonderful leaf peeping experience. Waking up and to breathe in the fresh mountain air, cozy up near the indoor fireplace with a cup of coffee. That is just a small slice of our paradise on the mountain.

Guest favorite

A treehouse and elevated deck are illuminated at night, showcasing warm lighting that highlights the rustic architecture. Outdoor seating is arranged around a fire pit, with lanterns lining the pathway. Surrounding trees create a natural backdrop, enhancing the enchanting atmosphere.

Treehouse in Stanardsville

4.85 out of 5 average rating, 141 reviews

Treehouse at Castle

Our cozy treehouse offers a one-of-a-kind accommodation, perfect for a romantic getaway or a peaceful retreat. The elevated deck provides breathtaking views of the surrounding woods, creating a magical setting for your stay. Inside, the treehouse is thoughtfully designed with rustic charm and modern comforts. The treehouse is equipped with a small kitchenette, allowing you to prepare simple meals and snacks. The bathroom, though compact, offers all the essentials.

Guest favorite

A spacious two-bedroom house is set amidst lush greenery, featuring a covered porch and a fire pit in the foreground. The property includes neatly arranged red chairs around the fire pit, with a gravel pathway leading to the entrance. A rural landscape with trees and a driveway complements the serene atmosphere.

Home in Stanardsville

4.9 out of 5 average rating, 125 reviews

Shifflett's Ole Homeplace - serene river getaway

Welcome to Shifflett’s Ole Homeplace. Two-bedroom house nestled in the Blue Ridge Mountains along a stocked trout river. Located within 10 minutes of the Shenandoah National Park- Swift Run Gap Entrance and Appalachian Trail Hiking entrance. Within 15 miles of 10 of the vineyards along the Monticello Wine Trail. Take a day trip to some of Central Virginia's attractions-Monticello, Montpelier, Ashlawn, Natural Bridge and Luray Caverns.