Sherando Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Sherando vacation rentals

Exterior

Brand new serene luxury cottage just off the Brew Ridge Trail

Brand new serene luxury cottage just off the Brew Ridge Trail
Afton
10.0 out of 10, Exceptional, (5 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 ￥12,023
￥25,204 total
includes taxes & fees
Apr 28 - Apr 29
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, (49 reviews)
"Comfy rooms, great layout, pretty scenery, exceeded expectations "
United States
Molly P.
The price is ￥25,547
￥47,816 total
includes taxes & fees
Mar 31 - Apr 1
Unique Cypress cottage, close to Charlottesville with mountain views.
Terrace/patio

Blair's Vintage Apartment Nestled in Wine Country

Blair's Vintage Apartment Nestled in Wine Country
Waynesboro
10.0 out of 10, Exceptional, (23 reviews)
"Had a fantastic time staying here. Apartment was super cozy and close to Shenandoah National Park. Deborah was a great hostess. "
United States
Matthew H.
The price is ￥15,648
￥35,187 total
includes taxes & fees
Mar 29 - Mar 30
Blair's Vintage Apartment Nestled in Wine Country
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, (69 reviews)
"Perfect location for multiple restaurants & some shopping.Very clean...enjoyable stay."
United States
Roberta F.
The price is ￥23,951
￥39,017 total
includes taxes & fees
Mar 29 - Mar 30
Stay in Crozet Train Suite in Downtown Crozet
Property grounds

The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (22 reviews)
"Very clean and central to the wineries."
United States
Cynda
The price is ￥23,136
￥50,727 total
includes taxes & fees
Mar 29 - Mar 30
The Cottage @ Afton Mountain- Close to Wineries!
Interior

High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (106 reviews)
"Such a lovely cottage in a great spot!We enjoyed Crozet and time at Praha bakery, Star Hill Brewery, King Family Vineyard, and Mint Springs Park!"
United States
Polly H.
The price is ￥31,934
￥52,258 total
includes taxes & fees
Apr 12 - Apr 13
High Street | Walk to Everything Crozet | Pet-Friendly
Terrace/patio

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (32 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
The price is ￥18,275
￥42,307 total
includes taxes & fees
Mar 29 - Mar 30
Wintergreen Condo -Steps to Ski and restaurants
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 ￥18,035
￥29,887 total
includes taxes & fees
Mar 31 - Apr 1
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
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, (97 reviews)
"Great spot for a stay, hostess was amazing, highly recommend!!"
United States
Charles R.
The price is ￥20,840
￥31,505 total
includes taxes & fees
Mar 30 - Mar 31
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Terrace/patio

Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Afton
9.8 out of 10, Exceptional, (13 reviews)
"Very tranquil place. "
United States
Thomas K.
The price is ￥21,878
￥50,210 total
includes taxes & fees
Apr 5 - Apr 6
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Exterior

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

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (105 reviews)
"Great stay with a fabulous view! Very cozy and comfortable! We had a wonderful little getaway!"
United States
Vicki E.
The price is ￥26,585
￥52,091 total
includes taxes & fees
Mar 31 - Apr 1
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
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, (178 reviews)
"Everything was amazing "
United States
Richard
The price is ￥23,152
￥31,380 total
includes taxes & fees
Apr 5 - Apr 6
Cozy cabin for 2 w/ great mt views & walking trails!
Property grounds

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, (149 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is ￥17,564
￥38,553 total
includes taxes & fees
Mar 31 - Apr 1
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Property grounds

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, (13 reviews)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
The price is ￥12,933
￥34,247 total
includes taxes & fees
Mar 29 - Mar 30
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Exterior detail

Little Mountain Haven. True ski-in, ski-out. First floor!

Little Mountain Haven. True ski-in, ski-out. First floor!
Wintergreen Resort
10.0 out of 10, Exceptional, (9 reviews)
"Great little ski and ski out Property"
United States
Richard
The price is ￥33,052
￥59,711 total
includes taxes & fees
Mar 29 - Mar 30
Little Mountain Haven. True ski-in, ski-out. First floor!
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, (54 reviews)
"Always a pleasant stay."
United States
MARJORIE
The price is ￥13,253
￥14,751 total
includes taxes & fees
Apr 16 - Apr 17
Affordable Suites of America Waynesboro
Exterior

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (8 reviews)
"We really enjoyed our stay here! Great location, and the condo was very clean and well stocked. Communication with the host was excellent as well. We look forward to returning back some day!"
United States
Alexander H.
The price is ￥15,229
￥44,751 total
includes taxes & fees
Mar 29 - Mar 30
Laurelwood Hollow: Walk to Ski & Swim
Property grounds

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (52 reviews)
"The space was great for a getaway, highly recommended."
United States
Matt E.
The price is ￥13,221
￥18,270 total
includes taxes & fees
Mar 30 - Mar 31
The Firefly Springhouse
Ravens Roost, 3 Bedrooms, Hot Tub, Mountain View | Terrace/patio

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 ￥23,240
￥35,718 total
includes taxes & fees
Apr 27 - Apr 28
Love Ridge Mountain Lodging
Exterior

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

Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (29 reviews)
"Well stocked house with great layout for families or two couples. Great kitchen setup with everything you’ll need. Close to the resort and skiing. Close to hiking trails. "
United States
Jeremiah H.
The price is ￥18,179
￥52,460 total
includes taxes & fees
Apr 16 - Apr 17
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-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

The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

10/10 Excellent
"It was wonderful"
MoJoe 1-night trip
Posted 10 hours ago
The Blackburn Inn and Conference Center

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?

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 Afton Mountain Vineyards and Blue Ridge Parkway North Entrance.

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.