Vacation rentals in Simmons Gap

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Top-rated vacation rentals in Simmons Gap

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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, 102 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

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

A new cottage is set against the backdrop of rolling hills and mountains, featuring a metal roof and welcoming porch. A hot tub is positioned on the patio, while a gravel path leads up to the house, surrounded by open farmland with a sunset in the distance.

Cottage in Elkton

4.99 out of 5 average rating, 176 reviews

Shenandoah River Retreat

New guest cottage with gorgeous view of the Massanutten and Blue Ridge Mountains, access to the South Fork of the Shenandoah River. Sit on the porch and soak it all in, enjoy the river, and local activities King size bed, gas range/fireplace, all new appliances Wi-Fi and TV for local stations and Roku. Surrounded by farm land, bucolic setting. 4.5 miles from Merck, 2.5 miles from Coors, 3.5 miles from Massanutten Resort, 14 miles to Shenandoah National Park, 13 miles to JMU. No pets or smoking

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, 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, 192 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, 319 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 white, two-story barn with a distinctive gabled roof stands against a clear blue sky. Two chairs are placed on the gravel patio in front of the entrance, with green grass and a silos visible nearby, surrounded by autumn foliage in the distance.

Barn in Elkton

5 out of 5 average rating, 272 reviews

Elkton Dairy Barn near Shenandoah National Park

Were you raised in a barn? No! Us either but here’s your chance to stay in our cozy, converted dairy barn, perfect for a romantic getaway. For generations, the barn was used to milk the dairy cattle on our farmette nestled at the foothills of Massanutten Resort & the Shenandoah National Park. The Dairy Barn makes a perfect small gathering home place. Just wait until you see the views of the Blue Ridge Mountains from the lofted bedroom & the breathtaking foliage from the screened porch.

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, 264 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

Top guest favorite

A vibrant sunset illuminates the sky with shades of orange and pink, casting a warm glow over the rolling hills. Lush greenery is visible in the foreground, complemented by scattered trees and shrubs, offering a serene view of the surrounding landscape.

Apartment in Stanardsville

4.97 out of 5 average rating, 229 reviews

Parker Mountain Carriage House Near SNP, UVA & JMU

Serene country living just 12 miles to Shenandoah NP & 19 pretty miles to UVA. 3.7 miles to Blue Ridge School. 35 miles to JMU, Harrisonburg. Enjoy beautiful mountain views, sunrises/sunsets from your own patio on 12 acres surrounded by mountains & 300 acre cattle farm. Wineries, Dining & Shopping are only minutes away. Peace & quiet, acres to explore, Parker Mountain Carriage House is above the garage, connected to the main house. We respect your privacy & are available as needed.

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, 167 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, 153 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.

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, 126 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.