Vacation rentals in Simmons Gap

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Top-rated vacation rentals in Simmons Gap

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Top guest favorite

Guest suite in McGaheysville

4.98 out of 5 average rating, 469 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+++!

Guest favorite

A dining area with a wooden table and six chairs is illuminated by natural light from large windows, offering views of the mountainous landscape. A granite countertop and wine glasses are visible in the foreground, enhancing the inviting vibe of the space.

Cabin in Stanardsville

4.96 out of 5 average rating, 113 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.

Top guest favorite

An aerial view displays a charming home surrounded by lush greenery, with expansive lawns and a paved driveway. The Blue Ridge mountains form a scenic backdrop, enhancing the serene landscape, which includes mature trees and well-kept gardens.

Home in Dyke

4.96 out of 5 average rating, 307 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.

Guest favorite

A log cabin is nestled among lush greenery, featuring a spacious wrap-around porch with warm lighting. The structure showcases a traditional wooden design, highlighted by a stone chimney. Nearby, vibrant blue and white flowers add a colorful touch to the landscape.

Cabin in Dyke

4.97 out of 5 average rating, 244 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

Barn in Elkton

5 out of 5 average rating, 249 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.

Top guest favorite

A winding pathway is observed within a cavern, bordered by natural rock formations. Illumination highlights the intricate textures of the stalactites and stalagmites, casting a warm glow over the scene. Visitors can be seen exploring the sights, surrounded by the natural beauty of the cave.

Cabin in Elkton

4.95 out of 5 average rating, 145 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.

Superhost

A spacious wooden deck extends towards a serene body of water, surrounded by trees. Soft outdoor lighting creates a gentle ambiance against the dusk sky, which transitions from deep blue to lighter hues. The deck features simple wooden chairs, inviting relaxation.

Guest suite in Stanardsville

4.82 out of 5 average rating, 570 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.

Guest favorite

A spacious deck is highlighted, featuring a dining table and a propane grill. A hanging basket chair and comfortable seating are positioned against the backdrop of vibrant greenery. Large windows of the cabin provide ample natural light, creating a welcoming outdoor living space.

Cabin in Free Union

5 out of 5 average rating, 145 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 serene pond is surrounded by lush greenery, reflecting the clear blue sky above. Various trees line the banks, creating a tranquil natural setting. The still water offers a peaceful atmosphere, inviting moments of relaxation and contemplation in a secluded outdoor space.

Guesthouse in Earlysville

4.98 out of 5 average rating, 359 reviews

Cottage at Frog Jump- woodland privacy at its best

Guesthouse ideal for two people. Small cottage (1 bed, 1 bath) is situated in a country setting on ten wooded acres along a large serene pond. It features a darling kitchenette with sink, fridge, microwave and toaster/convection oven. (No stove top, no oven.) You'll enjoy birdsong and views of various wildlife. A quiet, restful place to stay when you want to be near Shenandoah Nat’l Park, UVA, Charlottesville, Virginia wineries, Monticello, Montpelier, CHO, and other close-by attractions.

Guest favorite

Cottage in Crozet

4.91 out of 5 average rating, 179 reviews

Idyllic Cottage Retreat

Kick back and relax in this 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 favorite

The kitchen features a blend of modern and rustic design elements, highlighted by a polished copper countertop and a stone accent wall. Stainless steel appliances, including a refrigerator and built-in cabinetry, are complemented by under-cabinet lighting, creating a functional cooking space.

Cottage in Elkton

4.9 out of 5 average rating, 192 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.

Superhost

A spacious great room features a warm-toned wooden ceiling and large windows that frame mountain views. A comfortable sofa with neutral upholstery faces a modern TV and a gas fireplace. A dining area, highlighted by a long table, invites gatherings and overlooks the serene outdoors.

Cabin in Free Union

4.94 out of 5 average rating, 163 reviews

Views+Firepit+Games+Coffee *Discounted* 6/16-18

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.

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Popular amenities for Simmons Gap vacation rentals

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Other great vacation rentals in Simmons Gap

Top guest favorite

A welcoming bonfire area features a circular pergola with wooden benches surrounding a central fire pit. The area is set on a grassy landscape, with cozy cabins visible in the background, creating an inviting space for gatherings under the open sky.

Farm stay in Mount Sidney

5 out of 5 average rating, 5 reviews

Cabin 1 on 1Tribe Farm

ZackRating, 5 stars1 week ago

Absolutely perfect Air BnB! We had such a great stay. Cabins are a bit primitive with no heat or AC so be prepared - but we had everything we needed to have a comfortable night. The lounge areas and bathrooms/showers were the best part by far. The surrounding area is stunning as well. Can't wait to come back here for another trip to Shenandoah!

Top guest favorite

A bedside table is featured with a stack of books, including 'Red Sparrow' and 'The Giver.' A small tile with a bird image is positioned in front, while a white candle rests in a black dish filled with smooth stones, creating a serene setting.

Private room in Staunton

4.96 out of 5 average rating, 553 reviews

The Retreat at Bull Run - Dog-Friendly!

AlexRating, 5 stars1 week ago

Great stay. Worked perfect for a one night stop traveling thru town.

Top guest favorite

Private room in McGaheysville

4.95 out of 5 average rating, 315 reviews

Private Queen Suite Near Shenandoah National Park

KaitlynRating, 5 stars1 week ago

My partner and I had a lovely stay here and would highly recommend! The location is great and Jantena was helpful, friendly, and responsive.

Guest favorite

A screened sunroom features wooden flooring and is furnished with two comfortable chairs adorned with floral cushions, alongside a simple bench. The surrounding screens provide views of the lush greenery outside, merging indoor comfort with the natural landscape.

Cabin in Elkton

5 out of 5 average rating, 9 reviews

Shenandoah National Park: Cabin w/ Patio!

CassandraRating, 5 stars13 months ago

I loved the house, location, and scenery. The house had everything we needed. Some throw blankets would have been a nice added touch, but it didn’t take away from the amazing experience.

Guest favorite

A gentle creek flows through a forested area, surrounded by moss-covered rocks and leaf-strewn ground. Natural vegetation lines the banks, and several small cascades can be seen as the water meanders over the stones, creating a calming, serene environment.

Cabin in Elkton

5 out of 5 average rating, 12 reviews

Cozy cabin for 2 Near Skyline Dr & Massanutten Mtn

IsraelRating, 5 stars2 weeks ago

Kevin’s place is beautiful and peaceful. Pictures in the listing don’t do justice. This is also the more equipped AirB&B I have ever stayed in. It has everything to enjoy the nature and disconnect from the city noise. The location also is perfect to get into Shenandoah, the entrance is just about 10min driving.

A charming cottage is illuminated by warm light, nestled within a serene landscape. Surrounded by lush trees, the structure features a simple design with a welcoming front window. In the foreground, a wooden fence borders the grassy area, and a fire pit can be seen in the distance.

Farm stay in Dyke

4.77 out of 5 average rating, 144 reviews

Constellation Farm - Cottage Farm Stay

CameronRating, 5 starstoday

Although the house was a little tricky to find at first we had an amazing time. Clean house, lots of dishes for our group and a great night sky. If I were to visit Virginia again I would choose this place

A mare stands beside her young foal in a grassy pasture, surrounded by trees. A person is crouched down, engaging with the foal. A black wooden fence lines the area, complementing the serene rural environment.

Guesthouse in Free Union

4.87 out of 5 average rating, 246 reviews

Beckets Run Cottage, Free Union, VA

MatthewRating, 5 stars5 days ago

I only have good things to say about our stay. The property is really peaceful and pleasant. The place had great AC for sleeping and everything we needed. The host is very nice and friendly. I would definitely come back again!

Top guest favorite