Holiday rentals in Stuarts Draft

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Top-rated holiday rentals in Stuarts Draft

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Guest favourite

Cottage in Waynesboro

4.92 out of 5 average rating, 198 reviews

The Copper Cottage - near the Appalachian Trail

An antique fully renovated, cozy cottage that blends the character of saw milled wood beams, hand-crafted finishes, & local art with the modern comforts of Wi-Fi, Streaming TV, A/C, and a Jetted shower that might raise your attitude with the altitude! Walk to Historic Waynesboro (<1 mile) and the riverside park, or its restaurants and stores to entertain even the peculiar palate or collector. Fully fenced in back yard, so bring the pups or the kids, but watch for wildlife! Hiking store nearby.

8–15 Dec

$151 SGD per night

Guest favourite

Apartment in Wintergreen Resort

4.91 out of 5 average rating, 177 reviews

A True Mountain Getaway! Ski in/Ski out!

Located steps away from the top of the ski slopes at Wintergreen Resort. No snow? No problem! Enjoy the cool mountain breezes, hiking and climbing trails, mountain lakes with beaches, wineries, breweries and much much more. Restaurants and shopping within walking distance. Our place has a galley kitchen and small refrigerator, a large deck to enjoy a quiet dinner and has been newly decorated. There is a king sized bed and a smaller fold out sofa that could accommodate two small children.

26 Aug – 2 Sep

$131 SGD per night

Guest favourite

Guest suite in Waynesboro

4.98 out of 5 average rating, 193 reviews

The LoriAnn, A Boutique Stay New Sleep Number Bed

This beautifully restored 1940’s home is located in the City of Waynesboro just a short drive from the Blue Ridge Parkway. Modern amenities, complimentary breakfast items and assurance of comfort awaits! Enjoy one of a kind Autographed Movie and TV Memorabilia. The spacious front porch is all yours including a 100 yr old porch swing that belonged to my Great Grandmother. Along with the Parkway & Skyline Drive, enjoy Restaurants, Breweries, Vineyards, movie theaters and exploring Route 151.

12–19 Sep

$158 SGD per night

Guest favourite

Flat in Staunton

4.93 out of 5 average rating, 338 reviews

A Mid-Staunton Nights Dream

Get a great nights rest in a beautifully decorated apartment in the heart of Historic Downtown Staunton. Walking distance to Beverley Street and the warf business districts, you can enjoy your days exploring Stauntons beautiful downtown, or drive a short distance and enjoy the Shenandoah National Park. Enjoy the perfect date by going to a 5 star restaurant, and afterwards enjoy a play at the Blackfriars Playhouse, home of the American Shakespeare Center, all within walking distance.

29 Oct – 5 Nov

$150 SGD per night

Guest favourite

Flat in Staunton

4.96 out of 5 average rating, 476 reviews

The Little Yellow Hideaway (Apt in Historic Home)

Currently getting a bit of a makeover and upgrade, our roomy, walkout basement apartment with windows in every room is tucked away in the heart of downtown. It includes a deck to enjoy in the evening. A home dating to the 1800s, with loads of character and occasionally a bit of noise from the upper levels. Across from Mary Baldwin, a short walk downhill to the Black Friar Theater, 1 1/2 blocks from historic St. Francis Catholic Church. Also, a fenced-in yard shared with guests.

16–23 Oct

$148 SGD per night

Guest favourite

Cabin in Vesuvius

4.97 out of 5 average rating, 158 reviews

Whimsical Creekside Cabin

Escape to our cabin in the Blue Ridge Mountains! Fall asleep to sounds of Little Mary’s Creek, enjoy your coffee on the wrap around deck, or delight in exploring your own 7 acres in the forest. Our cabin is a cheerful, clean cottage to come home to- or decide to spend your days on property splashing in the creek and sitting out by the fire pit. We invite you to embrace our simpler way of life where we wholeheartedly believe that life is to be enjoyed and not endured.

27 Sep – 4 Oct

$158 SGD per night

Guest favourite

Home in Staunton

4.96 out of 5 average rating, 114 reviews

Queen City Cottage in Historic Downtown Staunton

Welcome to Queen City Cottage, a newly renovated, historic home in downtown Staunton. You'll be just steps from all of the fantastic dining, shopping, architecture, and entertainment that the city has to offer! This peaceful, stylish home has the best of both worlds; loads of historic charm with all of the modern upgrades you could hope for. Enjoy the spaciousness, the fun vintage elements, the comfort, and the incredible location!

11–18 Feb

$145 SGD per night

Guest favourite

Flat in Staunton

4.95 out of 5 average rating, 276 reviews

Travelers Nook - close to downtown

The TRAVELERS NOOK is a cute, cozy, one bedroom apartment close to downtown Staunton! It’s located on the second floor, with a private entrance. It has all the charm that you would expect to find in a cute studio apartment! Built by a local architect Tj Collins in the 1920’s. This quaint space has everything you need to enjoy your stay here in Staunton! We do accept small pets on approval with a pet cleaning charge.

3–10 Oct

$120 SGD per night

Guest favourite

Guest suite in Waynesboro

4.98 out of 5 average rating, 122 reviews

Spacious upstairs apartment with sunset views

We are located in Waynesboro next to Ridgeview Park and the South River. The park has tennis courts as well as a children’s playground and an outdoor swimming pool. We are within walking distance of the old downtown area of Waynesboro with restaurants, coffee shops and the Wayne Theater. We are a 10 minute drive to the Blue Ridge Parkway and Shenandoah NP, for wonderful scenery and hiking.

2–9 Jul

$185 SGD per night

Guest favourite

Bungalow in Waynesboro

4.89 out of 5 average rating, 170 reviews

NEW! Cheerful 2 bd bungalow with hot tub. Must see

Enjoy the entire home to yourself, including a relaxing backyard retreat with hot tub. Perfect for singles or couples who want to stay home and relax or visit the sites then come home to enjoy the hot tub under the stars. 10 min drive to shopping; 10 min to Blue Ridge Parkway & Skyline Drive; 15 min to 151 Breweries. kayaking/canoeing/hiking/fishing on the beautiful South River.

11–18 Jan

$208 SGD per night

Guest favourite

Guest house in Staunton

4.93 out of 5 average rating, 523 reviews

The Firefly Springhouse

Private cabin, with bath, located in a quiet country setting, close to town and easy access to two Interstate highways. Comfy queen bed, 400 ct sheets. Climate control with state of the art Trane system. Mini-fridge, microwave, and Keurig coffee maker are included. High speed wireless internet and basic cable TV. All varieties of people are welcome here.

27 Feb – 6 Mar

$131 SGD per night

Guest favourite

Guest house in Waynesboro

4.9 out of 5 average rating, 325 reviews

The Stable

Our guesthouse is located in the historic Tree Streets Neighborhood of Waynesboro, VA, an official Appalachian Trail town, located at the southern end of the Shenandoah National Park. We've aptly named the guesthouse "The Stable" because it was originally built and functioned as a stable. It has since been converted into a cozy cottage for guests.

28 Aug – 4 Sep

$115 SGD per night