Holiday rentals in Chestnut Hill

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Top-rated holiday rentals in Chestnut Hill

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Top guest favourite
Flat in Laurel Springs
4.98 out of 5 average rating, 127 reviews

Parkway Paradise | Cozy Retreat Blue Ridge Parkway

Our cozy studio apartment offers home-like comfort surrounded by nature. Pet-friendly and family-friendly amenities provide everything you need for a relaxing self-contained stay. Steps from the Blue Ridge Parkway, explore the countryside and the quaint mountain towns. The surrounding landscape ranges from grassy meadows to forests to the cliffs of the Bluffs, winding rivers and trails. Fully equipped studio, full kitchen, built above our garage. Mountain views, peaceful woods, bass pond. 🌲🏔️

Top guest favourite
A quaint cottage is surrounded by lush greenery, featuring a metal roof and an inviting garden with colorful flowers. A picnic table sits on a stone pathway leading to the front door, enhancing the outdoor space.
Guest house in Damascus
4.96 out of 5 average rating, 1,443 reviews

Ruby's Rest

NO CLEANING FEES. NO TO DO LISTS BEFORE CHECKING OUT. NO PET FEES. Cozy, private one room cottage (with bathroom), run by a loving, easy-going, non-judging family. Cottage measures 12' x 24' (total of 288sq. feet). Very relaxed environment. Flat rate of $50.00. UPDATE: Deck is now enclosed with old window panes. Super cozy. Has a sink with hot/old water, a hot plate, large toaster oven, and utensils. I am am still putting finishing touches on it, but available for use. Pictures soon.

Top guest favourite
The exterior of a charming house is shown, featuring a mix of gray and blue siding. A front porch with seating is visible, and a well-maintained lawn is surrounded by rolling hills in the background. The sky is partly cloudy, enhancing the serene setting.
Home in Jefferson
4.98 out of 5 average rating, 131 reviews

Autumn Acres -location-close to town/all amenities

Welcome to the coolest corner in NC, offering all 4 seasons. Make Autumn Acres your mountain getaway in beautiful Jefferson, NC. Enjoy sitting on the front porch taking in the view of Mt. Jefferson. Only minutes to local shops, restaurants, & all of the outdoor activities-Blue Ridge Parkway, Mt. Jefferson State Park, Ashe Park, kayaking, hiking & skiing. Autumn Acres offers 4 bedrooms, 2 full baths, fully stocked kitchen, huge dining, spacious living room, laundry/mud room, private back deck.

Top guest favourite
Tiny home in Warrensville
4.96 out of 5 average rating, 272 reviews

The Hobbit House

The Hobbit House is a tiny house (15x11'); Full size bed, futon/couch, outdoor tub, shower, electric fireplace, patio, picnic table, fire ring, and outhouse with composting toilet. The patio overlooks a pond and is part of a 53 acre forested property in the Blue Ridge. WiFi is now included. Glamp in style! The main lodge is just up the driveway if you need to contact the host. The outdoor shower/tub is NOT fully enclosed or private, and may be turned off in a freeze. Nature lovers only!

Guest favourite
A comfortable living area features a spacious leather sofa adorned with decorative pillows. A wooden coffee table sits in front, and a wall-mounted television offers entertainment options. Natural light filters through the window, while a gas fireplace adds warmth to the space.
Apartment in West Jefferson
4.95 out of 5 average rating, 218 reviews

Cozy 2BR, Pet-OK, Mountain Views, close to DT

Entirely renovated, this darling duplex overlooks the meadow with stunning mountain views. Located 5 min to charming downtown West Jefferson. This vacation spot has so much to offer! With its location, you can enjoy outdoor activities such as hiking, canoeing, kayaking, and fishing along the New River, nature walks and biking along the Blue Ridge PKWY. This unit is stocked with many convenient amenities and also offers an area for outdoor dining with a charcoal grill and an open fire pit.

Top guest favourite
A tiny house stands on a grassy hill under a starry night sky, illuminated by soft light from the porch. The rustic exterior features a combination of wood and metal, while the deck offers access to the serene landscape surrounding the property.
Tiny home in Fleetwood
4.94 out of 5 average rating, 445 reviews

Tiny House with GREAT VIEWS!

Our space, a custom build from HGTV-featured tiny house builder Randy Jones, is on a ridge with unparalleled, 270-degree views of Grandfather Mountain, all three area ski resorts, on into Tennessee and Virginia's Mount Rogers. We're located 20 minutes from Boone and 15 to West Jefferson, and even closer to the Blue Ridge Parkway and New River activities like fishing and tubing. If you've considered downsizing, or you just want to give living tiny a try for a getaway, this is the place!

Top guest favourite
Cabin in Watauga County
4.94 out of 5 average rating, 366 reviews

Charming Cabin farm-core aesthetic, 15 min 2 Boone

Cottage is situated overlooking gentle pastures and long range mountain views. A perfect front porch setting for those North Carolina Mountain sunsets offering a peaceful relaxing experience. The surrounding wildlife, forested area, hiking trails, and bold streams make this an adventurous getaway for the whole family. The Blue Ridge Parkway and New River are minutes away for fishing, biking and river fun. Boone, Jefferson, Appalachian State University are less then 12 miles near.

Guest favourite
Cabin in Mouth of Wilson
4.95 out of 5 average rating, 175 reviews

Rumple's Retreat Cabin - Arcade & Drive-in Theater

Rumple's Retreat is a cozy 2-story log cabin with an open loft with 2 queen beds. The property is minutes from Grayson Highlands State Park and all its attractions, 2 mi. to the entrance. Bring your quarters for the arcade full of retro classics! Outdoor private drive-in theater with a new movie every night! Relax by the campfire or fish the stocked Wilson Creek on the property. -Free to use kayaks, and canoes -High Speed WiFi across property -Pets allowed -3 vehicle limit

Top guest favourite
A deck area is furnished with two rattan chairs and a small table, offering an unobstructed view of Mount Jefferson and surrounding greenery. The open sky reveals a mix of clouds, creating a serene outdoor space for relaxation.
Home in Jefferson
4.97 out of 5 average rating, 188 reviews

Mt Jefferson View, modern & cozy

Welcome to Blue Horizon Hideaway! Enjoy an unbeatable view of Mount Jefferson with convenience to restaurants, breweries, shopping, hiking and the New River! The 14 foot walls and ample windows allow natural light to pour into every room. Relax while watching the sunsets and fall colors from the deck. Pictures do not do this hideaway justice, book now to take in the beauty of Mount Jefferson and the surrounding Blue Ridge Mountains.

Guest favourite
A rustic cabin is framed by lush greenery, with a warm wood exterior and a striking red roof. A large covered porch extends across the front, supported by wooden posts, and a set of steps leads up to the entrance.
Cabin in Mouth of Wilson
4.9 out of 5 average rating, 365 reviews

Briar Run Cabin near Grayson Highlands Park

Explore the creek, relax in the sauna, and enjoy the privacy of a secluded, two-acre tract adjoining the Jefferson National Forest, near Grayson Highlands’ wild ponies and White Top’s famed Creeper Trail. Bring your slingshots, sit on boulders, and warm yourself by one of two natural-stone fire pits. Help yourself to Starlink Wi-Fi and Roku to stream your favorite shows. This is one of the most untouched areas in America.

Top guest favourite
A rustic cabin with warm wooden siding sits in a vast grassy meadow surrounded by trees. A vibrant pink door serves as a focal point, and chairs are arranged on the porch. The clear blue sky enhances the serene outdoor setting.
Cabin in Grassy Creek
4.95 out of 5 average rating, 462 reviews

Grove Cabin 20 acres of privacy (no extra fees)

Nestled in a high mountain meadow just above the New River, this 750 square foot cabin has plenty of amenities and nearly 20 acres for your own private Idaho...there are marked and cleared hiking trails...look for the entrance post to the left "1285." NOTE: GPS systems are sending people to the coordinates of the cabin and not the entrance road. Always come in via NC-16--John Halsey-Weavers Ford-East Weavers Ford.

Top guest favourite
Cabin in Lansing
4.98 out of 5 average rating, 148 reviews

Historic Appalachian Log Cabin on 22 Idyllic Acres

Welcome to Long Branch Farm, a historic log cabin built in 1897 that sits on 22 beautiful and secluded acres. It's the perfect place to unwind and enjoy the freedom of open space. ~ 5 min to Lansing ~ 15 min to West Jefferson ~ 25 min to Grayson Highlands ~ 45 min to Boone Visit our café in downtown Lansing, the Old Orchard Creek General Store. We look forward to hosting you!

Popular amenities for Chestnut Hill holiday rentals