Guesthouse holiday rentals in Staunton

StreamSide Guesthouse in Mountains/National Forest

Stream-side guest house with charming views in lovely mountain setting; just steps from trailhead into GW National Forest. Peaceful, private and all to yourself, this 720 sq ft loft is a stylish, comfy retreat. During the day go hiking, wading, or just relax on the deck overlooking the stream. At night let sounds of rushing water and the gentle voices of nature lull you to sleep. Only 11 miles to Harrisonburg. Fast wifi with Prime/Netflix. A meditative retreat from which to explore the valley.

Mountain Cottage, Ski Wintergreen, Nelson 151

Wake to gorgeous Mountain views & rolling green meadows bordering the Rockfish River on our family estate. Private attached unit with built in pool (mid April-mid Sept)in the Blue Ridge mountains of Nelson County Virginia on the center of the 151 Brew Ridge Trail. Much preparation has gone into making your stay beautiful, convenient and comfy. No need to physically interact if that’s your desire. Enjoy swimming, hiking, kayaking, horse back riding, skiing, snowboarding, and more! 3 nite minimum

Entire Country Cottage guesthouse / Very Private

Gloriously private without feeling secluded, this charming guesthouse was totally updated in 2019. Enjoy the peace and quiet. Go for a walk or bike ride on the 28 plus acres or pretty rural lanes. 2.5 miles away is Lake Robertson for activities . Sit on the porch too! On a snowy night, enjoy the wd-burning fireplace . (We will often leave fireplace prepared to light. Gas heating also). Get cozy with the full kitchen, washer/dryer, games and books. DirecTv in the living room and bedroom. too!

Crozet Cottage | Close to Wineries & DT Crozet

Enjoy a cozy getaway at our centrally-located carriage house, in the heart of sought-after Crozet, VA. Completely renovated in 2022, the carriage house feels brand new! Our space offers 1 queen bed and 1 full-bed pull-out couch. The space is .5 miles from downtown Crozet, 2.5 miles to King Family Vineyard and 3.5 miles to Chiles Orchard. It is equipped with a kitchen, a large closet (fits a pack n' play!), high speed internet and Apple TV. We have assigned parking spots in the driveway.

Renew @ Coniferidge.

Constructed in 2017 “ Renew” offers a peaceful, clean and simple space furnished with a comfortable modern mix style. It is situated a short distance from the main home and offers just the privacy you are looking for. This property, located outside beautiful Charlottesville Va. is an easy drive to restaurants, shopping, art, culture, wineries, history, parks and the Uva . Flat Screen Smart TV (use your logins to access your favorite sites ) NO pets - out of consideration of future guests

Adorable Tiny House in Rawley Springs

Enjoy a stay at our efficient 10’x14’ tiny guest house on our “hobby farm” in Rawley Springs. If you’re looking to experience tiny living and for a nice place to rest after a day of hiking or exploring the beautiful Shenandoah Valley, we welcome you to our tiny house. It’s fully equipped with a comfortable and stylish pull out trundle bed, A/C, refrigerator with freezer, keurig, microwave, hot plate, and outdoor grill. WiFi and streaming services complimentary. Farm fresh eggs provided.

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)

Your Perfect Blue Ridge Mountain Hideaway near 151

A luxury tiny home built without compromise. This six-figure, custom-built retreat features high-end finishes, premium materials, and a refined layout that feels both elevated and comfortable. Set in the Blue Ridge Mountains, it offers privacy and tranquility with easy access to scenic drives, hiking, renowned breweries, and local wineries—ideal for a relaxed weekend escape focused on slowing down, good food and drinks, and returning home refreshed.

Little Cottage

Located in the Beautiful and historical Shenandoah Valley. If you enjoy outdoor activities, the Valley is the place to be. This 450 sq ft Studio is minutes from Jame Madison University, Bridgewater College, and Mary Baldwin University. Less than 2 miles from Blue Ridge Community College. 5 mins from Shenandoah Valley Regional Airport. Massanutten Resort is a short drive from this location. Located less than 1 mile from Interstate 81 exit 235.

Luxury tiny house 3 min from UVA

La Casita is a new tiny home combining modern luxury with central location adjacent to UVA, central to wineries, and 10 minutes from Monticello. La Casita is design built to offer custom furnishings and luxurious touches. We are in the residential pedestrian-friendly neighborhood of Fry's Spring, near I 64. Walk to restaurants and Scott Stadium. Enjoy all amenities including a high-speed internet.

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.

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, 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.