We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals in Simmons Gap

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Simmons Gap

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

0 of 0 items showing

1 of 3 pages

Cabin in Stanardsville

4.81 out of 5 average rating, 530 reviews

Farmview Cottage 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 kitchen and full bathroom. We are on the property in case you need anything. We allow up to two pets for a fee of $75. All amenities are open and operational at this time.

Barn in Elkton

5 out of 5 average rating, 205 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.

Cabin in Elkton

4.95 out of 5 average rating, 110 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.

Cabin in Free Union

5 out of 5 average rating, 103 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!

Cabin in Stanardsville

4.99 out of 5 average rating, 189 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.

Cottage in Crozet

4.91 out of 5 average rating, 139 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.

Place to stay in Stanardsville

4.84 out of 5 average rating, 334 reviews

Off the Beaten Path - Powell Mountain

This cabin is conveniently located near the Swift Run Gap entrance to Skyline Drive in Shenandoah National Park. Guests can enjoy hiking to water falls or to mountain peaks in the Park, then a trip to wineries/breweries in the Monticello district. Guests may enjoy an afternoon cooking out on the grill and relaxing in this secluded cabin in the mountains. On cool nights, the fireplace can provide warmth. The cabin is also about 20 miles from Massanutten Resort, straight along Rt 33.

Cabin in Free Union

4.95 out of 5 average rating, 146 reviews

Mountain Views + Firepit, Coffee Bar, Wifi, Games

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.

Guesthouse in Elkton

4.98 out of 5 average rating, 151 reviews

Carriage House private, 10 min to Shen. Nat'l Park

Private, well-appointed studio apartment. On same small farm property as main house, but separated with private entrance. Queen bed. View of the Massanutten Mountain range, grazing sheep, and beautiful sunsets. Centrally located just outside Elkton--15 minutes to Shenandoah National Park; 5 minutes to Massanutten Resort. Local restaurants, coffee shop, brewery, and town parks nearby. No smoking or pets.

Guest suite in McGaheysville

4.92 out of 5 average rating, 135 reviews

Shenandoah National Park getaway!

Enjoy your stay in our private apartment! Gorgeous mountain views - centrally located in the Shenandoah Valley. Take advantage of the close proximity to Shenandoah National Park - 9 miles/10 minutes to Swift Run Gap entrance! Less than a mile from Massanutten resort & just a short 5 minute drive to the Shenandoah River. Harrisonburg, JMU, EMU, and the many breweries/vineyards are all close by!

Farm stay in Stanardsville

4.86 out of 5 average rating, 389 reviews

"The Farmhouse"

1900's farmhouse situated on 11 secluded wooded acres, backing up to Kilauwren Winery a short 10 min hike away! Rustic country feel with modern touches. Full Kitchen and dining area. Classic front porch with swing. Lots of yard to enjoy with mountain views. Screened in back porch to enjoy sunsets. Very secluded! Please note, if you are bringing your pet, further details on fees are below.

Cabin in Stanardsville

4.86 out of 5 average rating, 567 reviews

Secluded Shepherds Cottage

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 kitchen and full bathroom.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Simmons Gap vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Simmons Gap

Guest suite in McGaheysville

4.98 out of 5 average rating, 451 reviews

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

Cottage in Timberville

4.96 out of 5 average rating, 203 reviews

The Orchard Oasis: Charming & Romantic Farm Stay

Guesthouse in Mount Crawford

4.96 out of 5 average rating, 140 reviews

Country Cabin near JMU/ Skyline Dr / Massanutten

Home in Mount Crawford

4.94 out of 5 average rating, 212 reviews

River Views, WiFi, HOT TUB, Firepit, Mins off I81!

Home in Dyke

4.95 out of 5 average rating, 286 reviews

Living Water Farm, Blue Ridge

Rental unit in Stanardsville

4.96 out of 5 average rating, 224 reviews

Parker Mountain Carriage House Near SNP, UVA & JMU

Farm stay in Harrisonburg

4.98 out of 5 average rating, 182 reviews

Hilltop Apartment at GlenDor Farm

Cabin in Stanardsville

4.98 out of 5 average rating, 197 reviews

Peaceful get-away or home base for adventure for 2

Destinations to explore