Sherando Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Sherando vacation rentals

Standard Suite, 1 Queen Bed | Private kitchen | Full-size fridge, microwave, oven, stovetop

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (57 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is ￥12,512
￥13,926 total
includes taxes & fees
May 21 - May 22
Affordable Suites of America Waynesboro
Exterior

Brand new serene luxury cottage just off the Brew Ridge Trail

Brand new serene luxury cottage just off the Brew Ridge Trail
Afton
9.8 out of 10, Exceptional, (6 reviews)
"The property was very clean and awesome! It met the needs of our 2 day stay with our pets. We would stay again!"
United States
Joni K.
The price is ￥10,120
￥22,953 total
includes taxes & fees
May 19 - May 20
Brand new serene luxury cottage just off the Brew Ridge Trail
Exterior

Unique Cypress cottage, close to Charlottesville with mountain views.

Unique Cypress cottage, close to Charlottesville with mountain views.
Charlottesville
10.0 out of 10, Exceptional, (51 reviews)
"Great stay, very friendly, responsive owners."
United States
David F.
The price is ￥30,884
￥54,128 total
includes taxes & fees
Jun 1 - Jun 2
Unique Cypress cottage, close to Charlottesville with mountain views.
Smart TV, DVD player, books, music library

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Roseland
10.0 out of 10, Exceptional, (103 reviews)
"This place is such a gem. Stunning property, clean, and comfortable. You can tell the hosts take a lot of pride in this place. Loved it. "
United States
Warren
The price is ￥20,589
￥31,126 total
includes taxes & fees
May 29 - May 30
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Fridge, microwave, oven, stovetop

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Wintergreen Resort
10.0 out of 10, Exceptional, (35 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
The price is ￥16,392
￥49,002 total
includes taxes & fees
May 18 - May 19
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Property grounds

Cozy cabin for 2 w/ great mt views & walking trails!

Cozy cabin for 2 w/ great mt views & walking trails!
Schuyler
10.0 out of 10, Exceptional, (183 reviews)
"Everything was amazing "
United States
Richard
The price is ￥21,817
￥29,836 total
includes taxes & fees
May 17 - May 18
Cozy cabin for 2 w/ great mt views & walking trails!
Property grounds

The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (26 reviews)
"Clean property, spacious kitchen, accurate description, the laundry in the property added to the convenience. It was pleasant to stay in the property. Just make sure to get in touch with the host the night before check in or few hours before, because they might not respond back right away and the key to the property is a bit tricky."
United States
Caroline
The price is ￥22,949
￥50,317 total
includes taxes & fees
May 18 - May 19
The Cottage @ Afton Mountain- Close to Wineries!
Exterior

Whimsical Creekside Cabin

Whimsical Creekside Cabin
Vesuvius
10.0 out of 10, Exceptional, (59 reviews)
"The place & everything was great!"
United States
Major G.
The price is ￥17,422
￥37,436 total
includes taxes & fees
May 28 - May 29
Whimsical Creekside Cabin
Exterior

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Montebello
10.0 out of 10, Exceptional, (58 reviews)
"Beautiful location, great hosts, perfect trip. If you’re looking for a quiet getaway, this is the place. "
United States
Adam L.
The price is ￥22,965
￥36,640 total
includes taxes & fees
May 17 - May 18
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
1 bedroom, iron/ironing board, free WiFi, bed sheets

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (14 reviews)
"Had a great stay, location was perfect! Condo was very nice. "
United States
Alicia K.
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Exterior detail

Stay in Crozet Train Suite in Downtown Crozet

Stay in Crozet Train Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (70 reviews)
"The apartment was beautifully decorated and immaculately clean. It was close to everything we intended to get to and we appreciated how easy it was to check in and check out. It was so comfortable and homey. "
United States
Natalie
The price is ￥23,757
￥38,521 total
includes taxes & fees
May 17 - May 18
Stay in Crozet Train Suite in Downtown Crozet
Terrace/patio

Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Afton
9.6 out of 10, Exceptional, (15 reviews)
"This house was lovely for our small family. The hot tub, the proximity to ski resort. Highly recommend!"
United States
Megan B.
The price is ￥21,701
￥50,871 total
includes taxes & fees
May 19 - May 20
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Outdoor dining

Wandering Bear’s Den Private Studio Near Crozet and Charlottesville

Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
Charlottesville
10.0 out of 10, Exceptional, (58 reviews)
"Great little place! I fit our needs perfectly."
United States
Betsy D.
The price is ￥19,798
￥26,250 total
includes taxes & fees
May 26 - May 27
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
Fireplace

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
10.0 out of 10, Exceptional, (49 reviews)
"Very good host, good with communication! Nice clean place to stay and close to a lot of the places we were wanting to go!"
United States
Meredith T.
The price is ￥14,932
￥36,689 total
includes taxes & fees
May 17 - May 18
Where the Trail Ends
Outdoor dining

Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen
Roseland
10.0 out of 10, Exceptional, (16 reviews)
"Great stay! Thank you!"
United States
Lauren
The price is ￥20,355
￥45,982 total
includes taxes & fees
May 17 - May 18
Historic Bungalow 30 minutes from Wintergreen
Exterior

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (8 reviews)
"Great location, everything we needed. Great hosts"
United States
Natalie A.
The price is ￥15,046
￥44,212 total
includes taxes & fees
May 17 - May 18
Laurelwood Hollow: Walk to Ski & Swim
Exterior

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (32 reviews)
"Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!"
United States
Courtney S.
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Exterior

New cabin 1 mile from Blue Ridge Parkway. Minutes from Appalachian Trail

New cabin 1 mile from Blue Ridge Parkway. Minutes from Appalachian Trail
Montebello
9.4 out of 10, Exceptional, (10 reviews)
"The property was very clean and located on scenic property. The owner provided many extra perks such as firewood, fire pit, grill, cooking materials, and several toiletries! Would definitely recommend this location to anyone!"
United States
Donna
The price is ￥22,965
￥36,106 total
includes taxes & fees
May 27 - May 28
New cabin 1 mile from Blue Ridge Parkway. Minutes from Appalachian Trail
Exterior detail

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Waynesboro
10.0 out of 10, Exceptional, (20 reviews)
"The perfect stay for a wedding weekend in Waynesboro. It was very warm and accommodating and I can’t say enough good things about it. Thank you for a great weekend"
United States
Michael W.
The price is ￥17,960
￥29,859 total
includes taxes & fees
May 27 - May 28
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Interior

High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (108 reviews)
"Very clean and amazing location. Owners are very communicative. We certainly plan on returning in the future. "
United States
Anthony C.
The price is ￥31,676
￥52,742 total
includes taxes & fees
May 17 - May 18
High Street | Walk to Everything Crozet | Pet-Friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sherando Hotel Reviews

Motel 6 Staunton, VA

Motel 6 Staunton, VA

6/10 Okay
"As we drove down the long driveway, it reminded us of a horror movie it was dark very dark. Check in the lady was very nice. We checked into our room, the floor hadnt been swept, no big deal. When i che k in i always check for bugs. No bugs thats great. Well the sheets were dirty one had a snot rocket blown into it so i looked at the head of the bed and the sheets were even worse with grub. The other bed wasn't as bad. The bathroom shower was gross, if there would have been a better option we would have left . Instead we took a chance and stayed. Considering it being right next to the high way it was very quiet. "
Alexandria 1-night trip
Posted 1 hour ago
Motel 6 Staunton, VA

Find out more about Sherando

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Look no further and take a look at our great range of rental properties in Sherando!

Frequently asked questions

Can I find vacation rentals in Sherando?

Yes, we have vacation rentals close to well known points of interest in Sherando, or you can select a secluded option if you're looking for relaxation. Sherando is known for its parks.

What are some of the best vacation rentals in Sherando?

Bud's Place, Southern Charm in the Shenandoah Valley of Virginia: Located near Sherando, this vacation home rental is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Sherando?

Explore the area and family-friendly sights such as War Fields, or get out into nature at a spot like George Washington National Forest. In the larger area, you’ll find Raven's Roost Overlook and Afton Mountain Vineyards.

What’s a vacation rental in Sherando like?

A vacation rental is a private property you can stay in for a couple of days or more in Sherando. Vacation rentals feature extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for small groups.