Vacation rentals in Simmons Gap

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Top-rated vacation rentals in Simmons Gap

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Top guest favorite

A cozy living area features a stone fireplace with an electric insert, providing warmth and ambiance. A large TV is mounted on the wall, and the space is furnished with two white leather chairs, a footrest, and a small desk next to a window with natural light.

Guest suite in McGaheysville

4.98 out of 5 average rating, 483 reviews

Cozy 'For-Rest Retreat' by Nat'l Park, Resort, JMU

Solo travelers, couples, or two adults will love our homey (NOT chic, sleek nor spare), lower-level private suite set in the 4-season Massanutten Resort in lovely Shenandoah Valley. We are 3-8 mins to fun seasonal activities (WaterPark, trail rides, slopes, golf, go-karts, etc.); 15 mins to Shenandoah Nat'l Park's Swift Run Gap entry; 18-20 mins to JMU; 5-60+ mins to restaurants, wineries, antiquing, breweries, caves, hiking, biking, history sites, river sports, Amish markets, country drives+++!

Top guest favorite

A vibrant garden features a variety of flowers and lush greenery, showcasing colors like red, purple, and yellow. The farmhouse, with its white exterior, is framed by trees and mountains in the background, creating a serene outdoor setting.

Farm stay in Elkton

4.97 out of 5 average rating, 104 reviews

Duck Inn B&B at Small Axe Farms

Unique private space on our small family farm. Relax on our large deck, walk our property, or explore the local area. Option to add homecooked breakfast and dinner. Great location : 8 mi to Massanutten (snow sports, arcade, golf, waterpark, mountain biking); 5 mi to Shenandoah Nat'l Park (hike, scenic cycling/drive); 4 mi to Shenandoah River (fish, kayak, rafting, tubing); 3 mi to Elkton (award-winning brewery, excellent local restaurants, and shops); 20 mi to JMU, 35 mi to Charlottesville/UVA

Top 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, 124 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, 194 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, 320 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 rustic log cabin is surrounded by lush greenery, featuring a large wrap-around porch with multiple access points. A stone chimney rises from the side of the building. Soft lighting emanates from the windows, highlighting the natural wood structure.

Cabin in Dyke

4.97 out of 5 average rating, 265 reviews

Shenandoah Getaway Cabin on 5 Acres w/ *Hot Tub*

Our Log Cabin has EVERYTHING you need for your mountain vacation! Miles of gorgeous mountain views off the large wrap around porch. *Outdoor Hot Tub *Indoor Wood Burning Fire Place *15 minutes from Shenandoah National Park *30+ Local Wineries!! *Outdoor Firepit *1GB WIFI and Huge TVs! *Close to UVA/ Charlottesville *Full Kitchen *Large, Private Deck with Mountain Views *Propane Grill *Outdoor Heater *Plenty of Space to Park Cars *Hiking *Maybelle's General Store less than a mile away

Superhost

A spacious green lawn is bordered by a dense forest with various trees. Large boulders are scattered throughout the grass, and a bright blue sky filled with soft, white clouds is visible above, creating a serene natural setting.

Home in Stanardsville

4.79 out of 5 average rating, 448 reviews

Zen River Retreat

Secluded unique wood and stone home an 65 beautifully landscaped acres with 2,000 feet of river frontage. Large deck with picturesque views, soothing river sounds, and song birds, with lots of walking trails, just a few minutes from the Shenandoah National Park. Swimming hole, and picnic area with fire pit. Large open Dining/Kitchen area with glass front wood stove. Den with a queen sized futon sofa, for extra guests ($30 per person, per night). We allow up to two pets for a fee of $80.

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, 168 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

A covered porch features wooden railings and a rocking chair, offering a peaceful space to enjoy nature. The porch is surrounded by scenic views of the Appalachian Mountains, with sunlight casting shadows on the wooden deck.

Cabin in Elkton

4.93 out of 5 average rating, 154 reviews

Wood Haven Lodge

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.

Top 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, 128 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.

Top guest favorite

A charming roadside cottage is presented, featuring a stone exterior with large windows. The metal roof reflects natural light, while surrounding greenery complements the structure. A gravel area is visible in front, providing convenient access to the entrance and nearby steps.

Cottage in Elkton

4.9 out of 5 average rating, 204 reviews

Bridge House, 10 min to Shen. Nat'l. Park

Roadside cottage remodeled in 2021, conveniently located, fully appointed, in historic 1800s ice house in the town of Elkton. Built into a massive limestone outcropping; open concept design, cathedral ceilings, 1 queen bedroom, full bath, open kitchen/living area, copper bar. Private gravel parking lot beside cottage. Steps away from the Shenandoah River, a craft brewery & eateries; 10 min. to: Skyline Drive/nat'l. park; water park/ski resort; winery. No smoking, events or pets.

Top guest favorite

A charming two-story farmhouse is nestled among lush trees, featuring a stone chimney and a wide front porch. The exterior showcases white siding, and the surrounding landscape features a grassy yard with large rocks and greenery, creating a serene natural setting.

Home in Stanardsville

4.95 out of 5 average rating, 173 reviews

Peaceful Shenandoah Farmhouse ▲ Hightop Hideaway

Soak up all that Mother Nature has to offer surrounded by the trees of Shenandoah National Park, in our farmhouse nestled in the foothills of the Blue Ridge Mountains. This spacious, child and dog friendly home is a perfect place to escape and reconnect. Hike, explore the nearby vineyards, or just relax on the porch. It also can make a great remote work getaway with fast 100 mbps internet throughout the house. Set on 4 acres of private land, there is no shortage of fun to be had!