Holiday Rentals in Sherando

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Our top choices for Sherando holiday 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 €79
includes taxes & fees
22 Apr - 23 Apr
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 €295
includes taxes & fees
26 Apr - 27 Apr
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 €227
includes taxes & fees
20 Apr - 21 Apr
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 €286
includes taxes & fees
20 Apr - 21 Apr
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.
The price is €487
includes taxes & fees
20 Apr - 21 Apr
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 €295
includes taxes & fees
24 Apr - 25 Apr
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 €211
includes taxes & fees
20 Apr - 21 Apr
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 €267
includes taxes & fees
20 Apr - 21 Apr
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 €281
includes taxes & fees
28 Apr - 29 Apr
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, (151 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is €215
includes taxes & fees
22 Apr - 23 Apr
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 €333
includes taxes & fees
3 May - 4 May
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 €871
includes taxes & fees
20 Apr - 21 Apr
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.
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 €108
includes taxes & fees
20 Apr - 21 Apr
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 €185
includes taxes & fees
20 Apr - 21 Apr
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 €228
includes taxes & fees
27 Apr - 28 Apr
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 €211
includes taxes & fees
20 Apr - 21 Apr
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.
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 €288
includes taxes & fees
20 Apr - 21 Apr
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 €331
includes taxes & fees
20 Apr - 21 Apr
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

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 €108 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?

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious: This holiday home rental outside of Sherando is located in a rural location, and has a fireplace, a balcony and a BBQ 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 that 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 wider area, you’ll find Humpback Rocks and Afton Mountain Vineyards.

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.