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

RATED A TOP RIVER CABIN In Virginia. Stunning views! The heart of Nelson County.

RATED A TOP RIVER CABIN In Virginia. Stunning views! The heart of Nelson County.
Faber
10.0 out of 10, Exceptional, (53 reviews)
"Great cabin, very peaceful. John communicated everything perfectly. One of the best places we have stayed"
United States
Timothy D.
The price is CA $370
CA $472 total
includes taxes & fees
Apr 26 - Apr 27
RATED A TOP RIVER CABIN In Virginia. Stunning views! The heart of Nelson County.

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (33 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
The price is CA $156
CA $367 total
includes taxes & fees
Apr 21 - Apr 22
Wintergreen Condo -Steps to Ski and restaurants

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 $464 total
includes taxes & fees
Apr 21 - Apr 22
High Street | Walk to Everything Crozet | Pet-Friendly

Birds and Bees Cottage

Birds and Bees Cottage
Crozet
10.0 out of 10, Exceptional, (45 reviews)
"We had a great time and really enjoyed the fire pit."
United States
Craig F.
Birds and Bees Cottage

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (108 reviews)
"Very nice, updated place with everything we needed. We would definitely stay here again!"
United States
Kimberly M.
The price is CA $185
CA $395 total
includes taxes & fees
Apr 27 - Apr 28
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

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 $338 total
includes taxes & fees
Apr 21 - Apr 22
Stay in Crozet Train Suite in Downtown Crozet

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 $428 total
includes taxes & fees
Apr 21 - Apr 22
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

The Barn at Haden near Wineries and C'ville

The Barn at Haden near Wineries and C'ville
Crozet
10.0 out of 10, Exceptional, (126 reviews)
"Location is amazing and the place is so cute! Would definitely stay again! "
United States
Crystal L.
The price is CA $265
CA $453 total
includes taxes & fees
Apr 21 - Apr 22
The Barn at Haden near Wineries and C'ville

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 $343 total
includes taxes & fees
Apr 21 - Apr 22
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Lofty Pursuits: Spectacular View + EV Charger

Lofty Pursuits: Spectacular View + EV Charger
Treeloft
10.0 out of 10, Exceptional, (18 reviews)
"Will definitely stay at this location again!!"
United States
Richard W.
The price is CA $231
CA $536 total
includes taxes & fees
Apr 26 - Apr 27
Lofty Pursuits: Spectacular View + EV Charger

Red White & WTG: Game Room + Hot Tub

Red White & WTG: Game Room + Hot Tub
Pedlars Edge
10.0 out of 10, Exceptional, (8 reviews)
"I liked the following: -spacious house -supplies on hand -cleanliness of the house -location -quietness -# of bathrooms and bedrooms -no pets rule -no smoking rule -house decor"
United States
Deran
The price is CA $615
CA $1,404 total
includes taxes & fees
Apr 21 - Apr 22
Red White & WTG: Game Room + Hot Tub

New Listing!100 FT FROM THE SLOPES! 4bd/3bth Ski In/Out Dobie Condo + Loft ❄⛄⛷🏂

New Listing!100 FT FROM THE SLOPES! 4bd/3bth Ski In/Out Dobie Condo + Loft ❄⛄⛷🏂
Wintergreen Resort
9.6 out of 10, Exceptional, (15 reviews)
"Host was very responsive and helpful. Comfortable, spacious condo in a great slopeside location."
United States
Kendall P.
The price is CA $390
CA $852 total
includes taxes & fees
Apr 21 - Apr 22
New Listing!100 FT FROM THE SLOPES! 4bd/3bth Ski In/Out Dobie Condo + Loft ❄⛄⛷🏂

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (222 reviews)
"Nice place"
United States
Orhan
The price is CA $144
CA $160 total
includes taxes & fees
Apr 21 - Apr 22
Valley Extended Suites

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 21 - Apr 22
Love Ridge Mountain Lodging

Peacefull, private Cabin! 140 acres,mile of river trails! 10 minutes to Rt.151!

Peacefull, private Cabin! 140 acres,mile of river trails! 10 minutes to Rt.151!
Faber
10.0 out of 10, Exceptional, (56 reviews)
"The entire home was very clean and comfortable. The property is stunning and worth exploring. "
United States
Mario
The price is CA $288
CA $367 total
includes taxes & fees
Apr 27 - Apr 28
Peacefull, private Cabin! 140 acres,mile of river trails! 10 minutes to Rt.151!

Stay in Crozet Mountain Suite in Downtown Crozet

Stay in Crozet Mountain Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (121 reviews)
"Nice and clean, Charming Studio and right above a great coffee shop! Slept great and will stay again next time I'm in Crozet!"
United States
Matt C.
The price is CA $205
CA $338 total
includes taxes & fees
Apr 21 - Apr 22
Stay in Crozet Mountain Suite in Downtown Crozet

High Meadows--King BR, fireplace, jacuzzi, kitchen

High Meadows--King BR, fireplace, jacuzzi, kitchen
Lyndhurst
9.8 out of 10, Exceptional, (16 reviews)
"Nice quiet and clean. Fireplace was excellent. "
United States
april h.
The price is CA $294
CA $378 total
includes taxes & fees
Apr 22 - Apr 23
High Meadows--King BR, fireplace, jacuzzi, kitchen

Ivy Rose Cottage nestled b/t Cville & Vineyards

Ivy Rose Cottage nestled b/t Cville & Vineyards
Charlottesville
10.0 out of 10, Exceptional, (75 reviews)
"Loved staying here!"
United States
Rebecca E.
The price is CA $245
CA $463 total
includes taxes & fees
Apr 26 - Apr 27
Ivy Rose Cottage nestled b/t Cville & Vineyards

Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (3 reviews)
"Love the area"
United States
Toni
The price is CA $231
CA $534 total
includes taxes & fees
Apr 21 - Apr 22
Blackwood Chalet
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.