Sherando Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Sherando holiday rentals

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 NZ$244
includes taxes & fees
17 Mar - 18 Mar
Brand new serene luxury cottage just off the Brew Ridge Trail
10.0 out of 10, Exceptional, (48 reviews)
"We had a wonderful stay. We'll come back"
United States
Marilyn K.
The price is NZ$478
includes taxes & fees
10 Mar - 11 Mar
Unique Cypress cottage, close to Charlottesville with mountain views.

Cabin in Vesuvius

Whimsical Creekside Cabin
10.0 out of 10, Exceptional, (47 reviews)
"The cabin was very nice. "
United States
David F.
The price is NZ$372
includes taxes & fees
8 Mar - 9 Mar
Whimsical Creekside Cabin
10.0 out of 10, Exceptional, (12 reviews)
"Very tranquil place. "
United States
Thomas K.
The price is NZ$532
includes taxes & fees
8 Mar - 9 Mar
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
10.0 out of 10, Exceptional, (22 reviews)
"Yes, Cottage amenities adequate "
United States
CARL W.
The price is NZ$529
includes taxes & fees
9 Mar - 10 Mar
The Cottage @ Afton Mountain- Close to Wineries!
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 NZ$279
includes taxes & fees
6 Mar - 7 Mar
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
10.0 out of 10, Exceptional, (176 reviews)
"Amazing "
United States
Sylvester
The price is NZ$320
includes taxes & fees
8 Mar - 9 Mar
Cozy cabin for 2 w/ great mt views & walking trails!
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 NZ$408
includes taxes & fees
17 Mar - 18 Mar
Stay in Crozet Train Suite in Downtown Crozet
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 NZ$331
includes taxes & fees
16 Mar - 17 Mar
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Cabin in Lyndhurst

Love Ridge Mountain Lodging
3.0 star property
10.0 out of 10, Exceptional, (16 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is NZ$339
includes taxes & fees
9 Mar - 10 Mar
Love Ridge Mountain Lodging
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 NZ$559
includes taxes & fees
17 Mar - 18 Mar
High Street | Walk to Everything Crozet | Pet-Friendly
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 NZ$318
includes taxes & fees
9 Mar - 10 Mar
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
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 NZ$700
includes taxes & fees
11 Mar - 12 Mar
Hillside Haven: Modern Retreat, Mountain Views
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 NZ$384
includes taxes & fees
8 Mar - 9 Mar
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Holiday Home in Staunton

The Firefly Springhouse
9.8 out of 10, Exceptional, (49 reviews)
"The space was great for a getaway, highly recommended."
United States
Matt E.
The price is NZ$212
includes taxes & fees
26 Mar - 27 Mar
The Firefly Springhouse

Holiday Home in Roseland

Cozy Country small two bedroom home.
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 NZ$420
includes taxes & fees
6 Mar - 7 Mar
Cozy Country small two bedroom home.
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 NZ$368
includes taxes & fees
9 Mar - 10 Mar
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
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 NZ$341
includes taxes & fees
17 Mar - 18 Mar
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Apartment in Wintergreen Resort

Laurelwood Hollow: Walk to Ski & Swim
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 NZ$457
includes taxes & fees
12 Mar - 13 Mar
Laurelwood Hollow: Walk to Ski & Swim
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 NZ$560
includes taxes & fees
16 Mar - 17 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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

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, 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 NZ$214 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.