Holiday rentals in Simmons Gap

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Top-rated holiday 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, 148 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 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, 137 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.

Top guest favourite
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, 497 reviews

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

Solo travelers, couples, or two adults will love our homey (NOT chic, sleek or 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 favourite
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, 199 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

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, 226 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.

Guest favourite
Home in Elkton
4.94 out of 5 average rating, 222 reviews

Hottub 5 acres, Great hiking,The best views around

Stony Creek Lookout is a one-of-a-kind luxury retreat perched in the serene seclusion of the mountains.Brand new complete renovation, modern amenities, hot tub, sizable elevated deck, video/board games, theatre room, kayaks and high quality furnishings !This extraordinary stay adjoins the Shenandoah NatlPark with the best views in the Shenandoah Valley, hike out your back door. Pet friendly, 5 min from Massanutten 4 season resort, Shenandoah River & much more. Great Wifi & cell service! 5 TVs

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, 200 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.

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, 202 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 single-story house is framed by a large tree, with a fenced front yard featuring green grass. The house displays a mix of windows and a door beneath blue shutters, nestled in a peaceful, open landscape.
Cottage in Elkton
5 out of 5 average rating, 110 reviews

Country View Cottage-A home away from home!

Centrally located in the Shenandoah Valley 10minutes from the skyline drive. 15 m from JMU. Relax for the weekend while visiting your student Five minutes from Massanutten Resorts water park. Hiking, skiing, rafting and more! The views are spectacular! Visit great restaurants, breweries and wineries or just stay in and use our outdoor space with grill and firepit. Animals grazing nearby. Lots to do and see. Book your ski weekend. We are only 2 miles from the slopes! Bicyclist welcome!

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, 247 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.

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, 229 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, 180 reviews

Spring Escape w/ Gorgeous Mountain Views + Firepit

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.

Popular amenities for Simmons Gap holiday rentals

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