Vacation rentals in Simmons Gap

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Top-rated vacation rentals in Simmons Gap

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
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, 125 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 favourite
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, 261 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 favourite
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, 210 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 favourite
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, 184 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 favourite
A spacious bedroom showcases a large bed with elegant bedding, surrounded by wooden walls and ceiling. Rococo-style furnishings and decorative lighting add charm. A seating area features a vintage sofa. Natural light filters through multiple windows, creating a warm atmosphere.
Guest suite in Stanardsville
4.82 out of 5 average rating, 595 reviews

Cascina Rococo at White Lotus Eco Spa Retreat

Thank you for your interest in staying here. We are taking every precaution possible to ensure the safety of our staff and guests by using CDC approved sanitizers exclusively and we are disinfecting all door handles, switches, remotes, cabinets, appliances etc. Your room is self check-in with private (key code) entrance, full bathroom, refrigerator, microwave oven, dishes, utensils, etc. We are on the property in case you need anything. All amenities are open and operational at this time.

Top guest favourite
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, 183 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 favourite
A charming log cabin with a dark metal roof features a welcoming front porch adorned with potted flowers and decorative pumpkins. The rustic wooden door adds character, while the surrounding grassy area and trees provide a natural setting against a backdrop of distant mountains.
Cabin in Stanardsville
4.99 out of 5 average rating, 235 reviews

Cabin at Rabbit Hollow

Charming log cabin nestled in a glen by the Shenandoah National Park is an ideal retreat for a romantic get-a-way. The first floor contains a beautiful kitchen, dining area, full bathroom featuring a whirlpool tub, and cozy living room with a wood burning fire place. The second level holds the bedroom with a comfortable king size bed and a half bathroom. There are two porches where guests can relax with their morning coffee or evening cocktails while enjoying the wooded and mountain views.

Guest favourite
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 homes in Free Union
4.95 out of 5 average rating, 142 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 favourite
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
4.91 out of 5 average rating, 215 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.

Guest favourite
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, 175 reviews

Panoramic Views + Fireplace + Firepit - DEC 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.

Top guest favourite
A grassy open area is depicted, with a black and white dog lying comfortably on the ground. In the background, several canoes are visible on a trailer, positioned under trees that provide partial shade.
Guest suite in Charlottesville
4.92 out of 5 average rating, 154 reviews

The Brothers Great Room

Your private guest suite is located in Northern Albemarle County Virginia. We cannot allow cats(due to family members with allergies and the extra cleaning required) We are just off of Route 29 with easy access to local venues. The suite is up one flight of stairs. Albemarle County is central to the University of Virginia, Monticello, Montpelier, wineries, craft beer breweries, and wedding venues in the area. Your dogs may run the open areas. Please clean up after your pet.

Top guest favourite
The living room features two comfortable sofas, a coffee table with books, and a 55-inch TV. Natural light shines through windows that frame a relaxed setting. A dining area with wooden chairs and a small table is also visible, creating a cozy communal space.
Apartment in Harrisonburg
4.99 out of 5 average rating, 176 reviews

Close, Spacious, Fully Furnished, Breakfast

Treat yourself to this fully furnished, spacious, clean and quiet apartment with breakfast items provided to start your day. Just 3 miles from Rt 81 and close to JMU, EMU, easy access to Shenandoah National Park, Massanutten Resort, Sentara Medical Center & shopping. Relax and refresh in a home-like atmosphere with a living room, well-stocked kitchen, study area, laundry, bedroom with a walk-in closet, and many amenities. Your comfort is our concern.

Popular amenities for Simmons Gap vacation rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Greene County
  5. Simmons Gap