Vacation rentals in Simmons Gap

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Top-rated vacation rentals in Simmons Gap

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Guest favorite

Apartment in Elkton

4.98 out of 5 average rating, 190 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.

Dec 2 – 9

G$18,019 GYD per night

Guest favorite

Home in Stanardsville

5.0 out of 5 average rating, 298 reviews

Sister's View

A refurbished 1950's country cottage, adjacent to 80 beautiful acres, overlooks the Blue Ridge Mountains. The house has high-speed internet. Enjoy an amazing sunrise while sitting on your bedroom deck sipping coffee. View sunsets from the front porch with a glass of wine purchased from local vineyards. Whether visiting UVa, hiking in the Blue Ridge Mountains, touring the local wineries, craft breweries, or attending an event at the Barn at Edgewood - Sister's View will make your visit complete.

Jul 8 – 15

G$30,294 GYD per night

Guest favorite

Guest suite in McGaheysville

4.98 out of 5 average rating, 419 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+!

Nov 20 – 27

G$16,667 GYD per night

Superhost

Guest suite in Stanardsville

4.84 out of 5 average rating, 492 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.

Feb 2 – 9

G$16,233 GYD per night

Guest favorite

Guesthouse in Earlysville

4.98 out of 5 average rating, 316 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.

Jan 3 – 10

G$19,383 GYD per night

Guest favorite

Barn in Elkton

5.0 out of 5 average rating, 143 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 Skyline 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.

Apr 8 – 15

G$31,036 GYD per night

Guest favorite

Apartment in Stanardsville

4.96 out of 5 average rating, 214 reviews

Parker Mountain Carriage House- Near SNP, Wineries

Unwind with beautiful mountain views, gorgeous sunrises/sunsets from your own patio in the bird garden on 12 acres surrounded by mountains & neighboring 300 acre cattle farm. So many WINERIES, BREWERIES, DINING, SHOPPING are only minutes away. SHENADOAH NATIONAL PARK - 15 MIN drive Swift Run entrance. Waterfalls, hiking trails & horseback riding. BLUE RIDGE SCHOOL - 3 miles away. Hiking/ Biking trails CHARLOTTESVILLE , UVA - 25 -30 MIN drive HARRISONBURG, JMU- 45 MIN drive

Jun 27 – Jul 4

G$33,382 GYD per night

Guest favorite

Cabin in Free Union

4.97 out of 5 average rating, 123 reviews

Mountain Top Cabin w/ Amazing Views, Coffee, 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.

Aug 27 – Sep 3

G$89,630 GYD per night

Guest favorite

Cabin in Rockbridge Baths

4.97 out of 5 average rating, 268 reviews

Little Cabin in the Woods is quiet and secluded!

Enjoy our rustic, cozy, historic log cabin in the woods on 21 acres with two streams and a little meadow. The logs, from the 1800's, were reconfigured 17 years ago combining a rich history with high speed internet and modern amenities. Sink into the luscious bed with totally organic sheets, mattress topper, and pillows. Take a walk on the original wagon train road down to a stream or bath your senses in the majestic view of Jump Mountain from the meadow.

Oct 9 – 16

G$23,205 GYD per night

Guest favorite

Guest suite in McGaheysville

4.93 out of 5 average rating, 107 reviews

Beautiful Private Apartment near Massanutten

During December - all week nights $60 & weekends $80! Enjoy your stay in our private apartment! Gorgeous mountain views - centrally located in the Shenandoah Valley, less than a mile from Massanutten Resort. Take advantage of the close proximity to Shenandoah National Park - 9 mi/15 minutes to Swift Run Gap entrance! We are also just a short 5 minute drive to the Shenandoah River. Harrisonburg, JMU, EMU, and the many breweries/vineyards are all close by!

Jan 9 – 16

G$21,616 GYD per night

Guest favorite

Guesthouse in Elkton

4.99 out of 5 average rating, 114 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.

Feb 10 – 17

G$26,348 GYD per night

Guest favorite

Guesthouse in Elkton

4.99 out of 5 average rating, 162 reviews

Noná’s Nest

Noná’s Nest is a quaint one bedroom, one bathroom carriage house, tucked into the peaceful Shenandoah Valley. Centrally located 9.5 miles to the Swift Run Gap entrance of Shenandoah National Park, 12 miles to Massanutten Resort, and 22 miles to Harrisonburg. Enjoy the tranquil country setting and beautiful Blue Ridge Mountain views from the second story deck. Owners live adjacent to carriage house.

Oct 15 – 22

G$19,339 GYD per night