Holiday rentals in Simmons Gap

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Top-rated holiday rentals in Simmons Gap

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Top guest favourite
A modern cottage is nestled among vibrant autumn foliage, featuring a gravel pathway leading to the entrance. Large windows illuminate the building, while a covered porch invites relaxation. The surrounding landscape offers a serene green lawn, complemented by trees displaying fall colors.
Cottage in Elkton

Hot Tub*Near National Park & Massanutten*42 Acres

Seven Springs is a private, tranquil retreat on 42+ acres bordering Shenandoah National Park. Newly remodeled with modern comforts including a private hot tub, fireplace, Wi-Fi, and TVs in each bedroom and living room. Enjoy direct access to hiking, abundant wildlife, a screened porch, 12’ deep pond for fishing, and Elk Creek frontage. Just 15 minutes to Massanutten Resort for skiing and the indoor waterpark, 5 minutes to Shenandoah River access, and 15 minutes to the Swift Run Gap park entrance

FamilyLocationLaundry

4.99 out of 5 average rating, 126 reviews
Superhost
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

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.

LocationFamilyCheck-in

4.89 out of 5 average rating, 265 reviews
Superhost
Home in Elkton

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

LocationFamilyDecor

4.9 out of 5 average rating, 245 reviews
Top guest favourite
A spacious, two-story house with white siding and large porches is featured. Lush green grass surrounds the structure, and the landscape includes open pastures and trees. The setting is serene, with plenty of natural light illuminating the exterior.
Home in Dyke

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.

ValueFamilyRiver

4.96 out of 5 average rating, 361 reviews
Guest favourite
A rustic log cabin is surrounded by lush greenery, featuring a large wrap-around porch with multiple access points. A stone chimney rises from the side of the building. Soft lighting emanates from the windows, highlighting the natural wood structure.
Cabin in Dyke

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

FamilyValueLayout

4.96 out of 5 average rating, 333 reviews
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

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!

FamilyLocationCheck-in

4.99 out of 5 average rating, 247 reviews
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

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.

LocationFamilyWalkability

4.99 out of 5 average rating, 271 reviews
Top guest favourite
An open-concept living area features wood-paneled walls and high ceilings. Natural light floods through multiple windows, illuminating comfortable seating arrangements. A spiral staircase is visible in the background, while a dining table and colorful area rug add to the cozy ambiance.
Cabin in Elkton

One-of-a-kind cabin, hot-tub, near National Park

This is a year-round, stunning creekside oasis on 6 acres bordering the Shenandoah National Park & traversed by Hawksbill creek. Luxury & design meet chalet-style charm. This cabin is unlike any other! In summer, enjoy tubing on the Shenandoah river, hiking SNP, or wandering the 6-acre property bordering parkland. Visit the quaint town of Elkton and its wineries, breweries & antique stores. Experience nearby Massanutten Resort with its skiing, adventure park, etc. If you know, you know!

FamilyLocationGetting around

4.97 out of 5 average rating, 174 reviews
Top guest favourite
A charming two-story farmhouse is nestled among lush trees, featuring a stone chimney and a wide front porch. The exterior showcases white siding, and the surrounding landscape features a grassy yard with large rocks and greenery, creating a serene natural setting.
Home in Stanardsville

Hightop Hideaway – Cozy Secluded Mountain Retreat

Soak up all that Mother Nature has to offer surrounded by the trees of Shenandoah National Park, in our farmhouse nestled on 4 acres of private land in the foothills of the Blue Ridge Mountains. This spacious, child and dog friendly home is a perfect place to escape and reconnect. Hike, explore the nearby vineyards, gaze at the stars, tell stories around the fire, or just relax on the porch. It also makes a great remote work getaway with fast 100 mbps internet throughout the house.

LocationFamilyBreakfast

4.96 out of 5 average rating, 203 reviews
Top guest favourite
A vibrant sunset illuminates the sky with shades of orange and pink, casting a warm glow over the rolling hills. Lush greenery is visible in the foreground, complemented by scattered trees and shrubs, offering a serene view of the surrounding landscape.
Flat in Stanardsville

Parker Mountain Carriage House Near SNP, UVA & JMU

Serene country living just 12 miles to Shenandoah NP & 19 miles to UVA. 3.7 miles to Blue Ridge School. 35 miles to JMU, Harrisonburg. Enjoy beautiful mountain views, sunrises/sunsets from your own patio on 12 acres surrounded by mountains & 300 acre cattle farm. Wineries, Dining & Shopping are only minutes away. Peace & quiet, acres to explore, Parker Mountain Carriage House is above the garage, connected to the main house. We respect your privacy & are available as needed.

LocationValueIndoor spaces

4.97 out of 5 average rating, 237 reviews
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

Fall Foliage & Endless Blue Ridge Views. Fast Wifi

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.

FamilyLocationParks

4.95 out of 5 average rating, 199 reviews
Top guest favourite
Treehouse in Stanardsville

CloudPointe Retreat

Rare Appalachian Treehouse Gem! Luxurious, one-of-a-kind retreat for couples. Elevated tiny house among the treetops, private parking, plush bedroom, sleek bathroom, beautiful kitchenette, loveseat, lounge, private double-level decks, fireside lounging (wood provided), gas grill, and patio with a hot tub! Surrounded by nature, with wineries, hikes, restaurants and shopping all nearby. Please come and relax and revel in the beauty of nature! 4WD is highly recommended.

ValueFamilyCondition

4.98 out of 5 average rating, 134 reviews

Popular amenities for Simmons Gap holiday rentals