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, 189 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.

Sep 1 – 8

R1,656 ZAR per night

Guest favorite

Home in Stanardsville

5.0 out of 5 average rating, 297 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 9 – 16

R2,784 ZAR 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+!

Jul 26 – Aug 2

R1,384 ZAR per night

Superhost

Guest suite in Stanardsville

4.84 out of 5 average rating, 490 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.

Mar 19 – 26

R1,492 ZAR per night

Guest favorite

Guesthouse in Earlysville

4.98 out of 5 average rating, 314 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.

Dec 7 – 14

R1,781 ZAR per night

Guest favorite

Barn in Elkton

5.0 out of 5 average rating, 141 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.

Dec 16 – 23

R2,852 ZAR per night

Guest favorite

Guesthouse in Mount Crawford

4.95 out of 5 average rating, 107 reviews

Country Cabin near JMU/ Skyline Dr / Massanutten

Welcome to your very own country cabin getaway! As soon as you enter our property and take in the views we promise you will feel the stress of travel melt away. You will enjoy the scenic views of the Blue Ridge Mountains while being conveniently located minutes from shopping, JMU and all that Harrisonburg, VA has to offer. We are: 10 min to JMU Campus 10 min to Downtown Harrisonburg 15 min to Massanutten Four Season Resort 25 min to Shenandoah National Park (Swift Run Gap Entrance)

Aug 17 – 24

R1,848 ZAR per night

Superhost

Place to stay in Stanardsville

4.84 out of 5 average rating, 297 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.

Jan 17 – 24

R1,988 ZAR per night

Guest favorite

Cottage in Elkton

4.88 out of 5 average rating, 141 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.

Feb 18 – 25

R1,781 ZAR per night

Guest favorite

Cabin in Free Union

4.97 out of 5 average rating, 122 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.

Dec 15 – 22

R6,644 ZAR 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!

Nov 7 – 14

R1,995 ZAR per night

Guest favorite

Guesthouse in Elkton

4.99 out of 5 average rating, 159 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

R1,780 ZAR per night