Sherando Vacation Rentals

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Our top choices for Sherando vacation rentals

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (55 reviews)
"Always a pleasant stay."
United States
MARJORIE
The price is CA $114
CA $126 total
includes taxes & fees
Apr 22 - Apr 23
Affordable Suites of America Waynesboro

Whimsical Creekside Cabin

Whimsical Creekside Cabin
Vesuvius
10.0 out of 10, Exceptional, (52 reviews)
"Lovely cabin with great amenities"
United States
Austin L.
The price is CA $136
CA $303 total
includes taxes & fees
Apr 23 - Apr 24
Whimsical Creekside Cabin

High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (107 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 CA $274
CA $461 total
includes taxes & fees
Apr 21 - Apr 22
High Street | Walk to Everything Crozet | Pet-Friendly

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)
"Perfect location for multiple restaurants & some shopping.Very clean...enjoyable stay."
United States
Roberta F.
The price is CA $205
CA $336 total
includes taxes & fees
Apr 21 - Apr 22
Stay in Crozet Train Suite in Downtown Crozet

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 CA $154
CA $257 total
includes taxes & fees
Apr 22 - Apr 23
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (152 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is CA $151
CA $340 total
includes taxes & fees
Apr 22 - Apr 23
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

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, (180 reviews)
"Everything was amazing "
United States
Richard
The price is CA $193
CA $265 total
includes taxes & fees
Apr 22 - Apr 23
Cozy cabin for 2 w/ great mt views & walking trails!

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 CA $87
CA $198 total
includes taxes & fees
May 4 - May 5
Brand new serene luxury cottage just off the Brew Ridge Trail

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, (50 reviews)
"Comfy rooms, great layout, pretty scenery, exceeded expectations "
United States
Molly P.
The price is CA $226
CA $421 total
includes taxes & fees
Apr 26 - Apr 27
Unique Cypress cottage, close to Charlottesville with mountain views.

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, (57 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 CA $199
CA $314 total
includes taxes & fees
Apr 23 - Apr 24
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

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, (100 reviews)
"Great spot for a stay, hostess was amazing, highly recommend!!"
United States
Charles R.
The price is CA $178
CA $272 total
includes taxes & fees
Apr 27 - Apr 28
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (16 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is CA $192
CA $298 total
includes taxes & fees
Apr 22 - Apr 23
Love Ridge Mountain Lodging

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (318 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
The price is CA $142
CA $350 total
includes taxes & fees
Apr 27 - Apr 28
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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, (57 reviews)
"Great little place! I fit our needs perfectly."
United States
Betsy D.
The price is CA $171
CA $227 total
includes taxes & fees
Apr 21 - Apr 22
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville

Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.8 out of 10, Exceptional, (42 reviews)
"The location was great and the sunrise views were amazing!"
United States
Jennifer B.
The price is CA $190
CA $401 total
includes taxes & fees
Apr 21 - Apr 22
Panoramic Peak: Wintergreen Condo with Views

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 CA $188
CA $441 total
includes taxes & fees
Apr 21 - Apr 22
Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Cozy Country small two bedroom home.

Cozy Country small two bedroom home.
Roseland
9.8 out of 10, Exceptional, (19 reviews)
"Lovely cozy place in the mountains, we had a total blast!"
United States
Prabir
The price is CA $185
CA $340 total
includes taxes & fees
Apr 21 - Apr 22
Cozy Country small two bedroom home.

5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
Montebello
9.8 out of 10, Exceptional, (19 reviews)
"Heat works great. Very pet friendly. "
United States
Barbara L.
The price is CA $199
CA $314 total
includes taxes & fees
Apr 21 - Apr 22
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen
Roseland
10.0 out of 10, Exceptional, (15 reviews)
"Great stay! Thank you!"
United States
Lauren
The price is CA $176
CA $401 total
includes taxes & fees
Apr 21 - Apr 22
Historic Bungalow 30 minutes from Wintergreen

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 CA $142
CA $427 total
includes taxes & fees
Apr 21 - Apr 22
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
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

Find out more about Sherando

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Sherando. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious: This vacation home near Sherando is located in a rural location and has a fireplace, a balcony, 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. Kick off your shoes and enjoy yourself with a garden and 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 Humpback Rocks 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.