Holiday Rentals in Sherando

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Our top choices for Sherando holiday rentals

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 €129
includes taxes & fees
8 Mar - 9 Mar
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, (48 reviews)
"We had a wonderful stay. We'll come back"
United States
Marilyn K.
The price is €247
includes taxes & fees
10 Mar - 11 Mar
Unique Cypress cottage, close to Charlottesville with mountain views.

Whimsical Creekside Cabin

Whimsical Creekside Cabin
Vesuvius
10.0 out of 10, Exceptional, (47 reviews)
"The cabin was very nice. "
United States
David F.
The price is €191
includes taxes & fees
8 Mar - 9 Mar
Whimsical Creekside Cabin

Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Afton
10.0 out of 10, Exceptional, (12 reviews)
"Very tranquil place. "
United States
Thomas K.
The price is €275
includes taxes & fees
8 Mar - 9 Mar
Afton Cottage w/ Hot Tub, Firepit, Mountain Views

The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (22 reviews)
"Yes, Cottage amenities adequate "
United States
CARL W.
The price is €272
includes taxes & fees
8 Mar - 9 Mar
The Cottage @ Afton Mountain- Close to Wineries!

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, (56 reviews)
"The space was incredibly well furnished. Wi-Fi worked from the jump, check in was easy, host was very communicative. Great spot to stay!"
United States
Samuel M.
The price is €146
includes taxes & fees
7 Mar - 8 Mar
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville

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, (176 reviews)
"Amazing "
United States
Sylvester
The price is €166
includes taxes & fees
8 Mar - 9 Mar
Cozy cabin for 2 w/ great mt views & walking trails!

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 €211
includes taxes & fees
2 Apr - 3 Apr
Stay in Crozet Train Suite in Downtown Crozet

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, (94 reviews)
"Great spot for a stay, hostess was amazing, highly recommend!!"
United States
Charles R.
The price is €173
includes taxes & fees
12 Mar - 13 Mar
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 €171
includes taxes & fees
10 Mar - 11 Mar
Love Ridge Mountain Lodging

High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (105 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 €286
includes taxes & fees
8 Mar - 9 Mar
High Street | Walk to Everything Crozet | Pet-Friendly

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Ivy
10.0 out of 10, Exceptional, (42 reviews)
"It was a lovely place to stay and the hosts were so kind. "
United States
Cooper C.
The price is €165
includes taxes & fees
9 Mar - 10 Mar
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Hillside Haven: Modern Retreat, Mountain Views

Hillside Haven: Modern Retreat, Mountain Views
Faber
10.0 out of 10, Exceptional, (33 reviews)
"Fantastic property with all the amenities near UVA, and lots of wineries."
United States
roberto c.
The price is €354
includes taxes & fees
9 Mar - 10 Mar
Hillside Haven: Modern Retreat, 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, (51 reviews)
"Nice quite secluded get away with great hosts that check in and make sure everything is going well. Will be staying again and definitely recommend."
United States
Ryan C.
The price is €198
includes taxes & fees
8 Mar - 9 Mar
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (49 reviews)
"The space was great for a getaway, highly recommended."
United States
Matt E.
The price is €102
includes taxes & fees
8 Mar - 9 Mar
The Firefly Springhouse

Cozy Country small two bedroom home.

Cozy Country small two bedroom home.
Roseland
9.8 out of 10, Exceptional, (18 reviews)
"Lovely cozy place in the mountains, we had a total blast!"
United States
Prabir
The price is €214
includes taxes & fees
6 Mar - 7 Mar
Cozy Country small two bedroom home.

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, (12 reviews)
"We loved the 'ski-in/ski-out' convenience. Cute condo with everything you need for your stay. The water and snacks were a nice gesture. "
United States
Esperanza
The price is €188
includes taxes & fees
9 Mar - 10 Mar
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

NEW! Cheerful 2 bd bungalow with hot tub. Must see!

NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Waynesboro
9.8 out of 10, Exceptional, (48 reviews)
"loved the quiet location, sunny private back yard, and well-stocked kitchen"
United States
George D.
The price is €178
includes taxes & fees
9 Mar - 10 Mar
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

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 €238
includes taxes & fees
9 Mar - 10 Mar
Laurelwood Hollow: Walk to Ski & Swim

Ivy Rose Cottage nestled b/t Cville & Vineyards

Ivy Rose Cottage nestled b/t Cville & Vineyards
Charlottesville
10.0 out of 10, Exceptional, (70 reviews)
"Very warm, welcoming and cozy. Well equipped kitchen, comfy beds, cool bathrooms "
United States
Betty S.
The price is €292
includes taxes & fees
10 Mar - 11 Mar
Ivy Rose Cottage nestled b/t Cville & Vineyards
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

Everything you need to know about Sherando holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sherando holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sherando holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sherando holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sherando. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sherando holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sherando holiday rentals we have selected for you start as low as €109 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sherando rentals

At Expedia, we put the best Sherando holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sherando rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sherando holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sherando. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Sherando?

Yes, there are holiday rentals close to the most popular sights in Sherando, or you can select a more secluded option if you're looking for a relaxing stay. Sherando is known for its parks.

What are some of the best holiday rentals that Sherando has to offer?

4 BR cabin mins to trails & breweries pets welcome: This holiday home rental outside of Sherando offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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 wider area, you’ll find Afton Mountain Vineyards and Blue Ridge Parkway North Entrance.

What’s a holiday rental in Sherando like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sherando. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.