Holiday houses in Chestnut Hill

Tiny home in Warrensville

4.97 out of 5 average rating, 249 reviews

The Hobbit House

The Hobbit House is a tiny house (15x11'); Full size bed, futon/couch that sleeps an extra guest, outdoor claw foot tub, shower, electric fireplace, and outhouse with composting toilet. The tiny cabin has a patio, picnic table and fire ring. 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. FYI: Outdoor shower/tub is turned off in a freeze.

Tiny home in Warrensville

5 out of 5 average rating, 115 reviews

stylish modern cabin with panoramic views

Relax & recharge at this newly renovated log cabin with gorgeous wraparound views. Dine on the covered deck, sip wine at the firepit, listen to smooth jazz on bluetooth and sleep like a baby in the luxurious bedding. Stunning in every season! Mountaintop location w private drive. Fully stocked kitchen. 55" TV w Netflix, Hulu & more. FWD recommended in winter. Explore nearby wineries, hiking trails and kayak the New River. 15 min to shops & restaurants in charming downtown West Jefferson.

4.99 out of 5 average rating, 254 reviews

Cottage in Independence

Healing Water Falls

Disconnect and awaken your senses in this artisan home on 13 acres. Need WIFI & TV this rental is NOT FOR YOU. Looking for healing, inspiration, or reconnection this IS your place. Watch the falls from the comfort of your bed, or as you soak in the tub. Its sound infuses the entire house filling it with peace and tranquility. It's flow changes rapidly with rainfall. Come experience the restorative magic and stay in a place one guest swears was built "by garden gnomes and woodland fairies."

4.94 out of 5 average rating, 145 reviews

Chalet in Piney Creek

Mountain Getaway Chalet

Beautiful and Spacious 4 Bedroom/3 Bathroom fully furnished Mountain Chalet with Stunning mountain and sunset views. Completely re-varnished with gorgeous new color exterior both on the chalet and decks. Ring the bell on the porch and Feed the deer as they come right into the backyard on a nightly basis. The chalet fits perfectly from couples to multiple families or even just the solo adventurous traveler. There is a two-night minimum. On all major holidays there is a three-night minimum.

4.95 out of 5 average rating, 188 reviews

Condo in West Jefferson

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.

Tiny home in Mouth of Wilson

4.92 out of 5 average rating, 209 reviews

Pondside TinyHome near Grayson Highlands

Experience Tiny Home living Pondside! Enjoy amazing nature sounds, star gazing and pastoral horse farm views! Only a few miles from Grayson Highlands State Park known for its vistas and wild ponies. Explore Mt Rogers National Wilderness are, The Appalachian Trail, The Virginia Creeper Trail, the New River etc. close to wonderful restaurants and breweries, quaint towns and sight seeing. Step away and take a breath of fresh mountain air! *now pet friendly* NO cleaning or pet fees!

4.83 out of 5 average rating, 281 reviews

Loft in West Jefferson

Charming Loft in Downtown WJ w/Free Parking

Come and enjoy this stunning loft in the heart of Historical Downtown West Jefferson. Spend your days hiking trails off the Blue Ridge Parkway, fishing or floating down the New River, or just exploring all that downtown has to offer. After a long day of exploring and sampling bites and brews from the local downtown pubs and restaurants, simply walk back to your oasis overlooking town and recharge your batteries with some games or cozy up and watch your favorite movie.

4.95 out of 5 average rating, 115 reviews

Guesthouse in Creston

Boaz Brook Farm Guest House

If 24/7 entertainment is what you are looking for, continue your search. If serenity, peace, and enjoyment of mountain beauty is your wish, you have hit the jackpot! Don't worry, we have electricity, running water, and fiber optic WiFi. We feature a two-story, separate guest house in beautiful surroundings with a master suite upstairs including a queen bed, reading corner, TV area, and full bath. Downstairs you will find a kitchen, small bedroom, and a half-bath.

4.97 out of 5 average rating, 198 reviews

Cottage in Sparta

River Hill Hideaway

River Hill Hideaway is a cozy place of respite from the whirlwind called life. You can fish for bass, catfish and sunfish in the pond, or relax on the deck and listen to the river (if you can hear it over the crickets and frogs). The Little River (a trout stocked stream) bends just around the back of the property and you are welcome to fish there or enjoy the swimming hole. Be sure to get a NC fishing license if you plan to fish in the Little River.

4.99 out of 5 average rating, 114 reviews

Home in Troutdale

The Bluebird and Finch Cottage

Kick back and relax in this calm, stylish space looking out into the pasture and woodlands at deer passing through, cows looking in and other wildlife. And there really is quite a lot of bluebirds and finch to see in the spring and summer! Expect the coziness of the fireplace to wrap around you in the cool of the fall and snow of the winter. New construction. 20 minutes to Grayson Highlands, kayaking and Virginia Creeper bike trail also nearby!

4.98 out of 5 average rating, 197 reviews

Cabin in Laurel Springs

SECRET ESCAPE ON THE BLUE RIDGE PARKWAY. NC

HOUSE IS FINE❤️ Only damage we had was massive trees on driveway.❤️ The view is AMAZING. 6 1/2 Acres Nestled in Blue Ridge Mountains. Blue Ridge Parkway home is situated in the mountains of North Carolina, less than a .3 mile hidden driveway ON the Blue Ridge Parkway. The sunsets are amazing. Just take a scenic drive along the Parkway and enjoy many of the overlooks and views from all around! The home is a perfect place to recharge.

4.96 out of 5 average rating, 149 reviews

Home in Jefferson

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.

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Popular amenities for Chestnut Hill holiday rentals

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Free parking on premises

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Other great holiday rentals in Chestnut Hill

5 out of 5 average rating, 7 reviews

Cabin in Grassy Creek

Red White You Book Your Fourth of July Mountain

RobertRating, 5 stars7 months ago

All enjoyed the place. very clean. nice and serene. the last half mile is a little adventure for flatlanders but beautiful. I think what say it all is "we would do it again".

4.94 out of 5 average rating, 94 reviews

Cottage in Grassy Creek

Return To A Simpler Time at Lazy Y Mountain Farm

AnneMarieRating, 5 stars1 month ago

We loved our stay at this charming old farmhouse! The property is peaceful, beautifully kept, and surrounded by rolling pasture with cows grazing just beyond the fence—such a calm, grounding view to wake up to. The house itself has a cozy, historic feel with all the essentials, and it’s the perfect base for exploring the area. We went hiking at a Grayson Highlands, and the scenery was absolutely breathtaking—truly one of the most picturesque spots I’ve ever been. A perfect stay if you’re looking to unplug and enjoy nature.

4.86 out of 5 average rating, 91 reviews

Cabin in Piney Creek

Cozy and big cabin in the mountain. Stunning view

StephanieRating, 5 stars7 months ago

Very nice home. It was clean and has plenty of space. The view was very nice. We had a bit of trouble locating the gate entrance since we arrived after dark. The gate you enter in is on Frosty lane. Our host was super helpful.

4.95 out of 5 average rating, 41 reviews

Cabin in Crumpler

Sanctuary Hill- True Mountain Cabin on New River

Melissa AnnRating, 5 stars5 months ago

Brandon was wonderful to work with and extremely responsive. The cabin was rustic with up-to-date amenities. Beautiful property and such a calm peaceful place to get away and relax.

Tiny home in Mouth of Wilson

5 out of 5 average rating, 6 reviews

Ridgetop Retreat Arched Cabin - Arcade & Theater

KyleRating, 5 stars2 weeks ago

Excellent! Highly recommend!

4.89 out of 5 average rating, 18 reviews

Cabin in Crumpler

Indoor & Outdoor Fireplaces by Grayson Highlands

JennaRating, 5 stars1 month ago

The house was beautifully situated (that view and the hummingbirds!), clean and the description was very accurate. Jerrita was very professional, proactive and helpful. Highly recommended.

5 out of 5 average rating, 6 reviews

Cabin in Lansing

Riverfront Log Cabin w/ Hottub near West Jefferson

WilliamRating, 5 stars6 days ago

hot tub, river, sun porch, river, hot tub, decks, hot tub, grill, river, hot tub...in that order! well rested after taking in the beautiful scenic view, birds chirping, steam rising from the mountain after a morning rain shower, rocking chairs and coffee on the sun porch, the sound of the river to fall asleep to, silence, no highway traffic, no city noise, no sirens, no nonsense. close enough to town for your needs, but far enough to escape it all. three bedrooms on three separate floors is ideal for travel with little ones. full access to laundry and wifi, full access to property, helpful property owners are informative and friendly. would stay again, highly recommend.