Sherando Holiday Rentals

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Our top choices for Sherando holiday rentals

Rosé All Day: Wine Country Getaway! Walk to Dining

Rosé All Day: Wine Country Getaway! Walk to Dining
2.0 star property
Crozet
10.0 out of 10, Exceptional, (18)
"The house was clean, fully stocked kitchen, comfortable beds, nice big full bathroom, and convenient location!"
United States
Margaret W.
The price is AU$499
includes taxes & fees
14 Dec - 15 Dec
Rosé All Day: Wine Country Getaway! Walk to Dining

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (53)
"Always a pleasant stay."
United States
MARJORIE
The price is AU$139
includes taxes & fees
2 Jan - 3 Jan 2026
Affordable Suites of America Waynesboro

Bluebird Cottage: Near 151 + Appalachian Trail

Bluebird Cottage: Near 151 + Appalachian Trail
2.0 star property
Roseland
8.4 out of 10, Very good, (9)
"I contacted the owners to see if my family and I could check in earlier and they were about to accommodate for us. The home was clean, spacious, and had everything we needed for our stay."
United States
Sa'Mone M.
The price is AU$442
includes taxes & fees
14 Dec - 15 Dec
Bluebird Cottage: Near 151 + Appalachian Trail

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Montebello
10.0 out of 10, Exceptional, (13)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is AU$390
includes taxes & fees
15 Dec - 16 Dec
Love Ridge Mountain Lodging

Whimsical Creekside Cabin

Whimsical Creekside Cabin
Vesuvius
9.8 out of 10, Exceptional, (39)
"Had a very quiet relaxing stay "
United States
Joyce I.
The price is AU$301
includes taxes & fees
14 Dec - 15 Dec
Whimsical Creekside Cabin

Mechum Hill Cottage: Central to Crozet & Cville

Mechum Hill Cottage: Central to Crozet & Cville
Charlottesville
9.6 out of 10, Exceptional, (17)
"Very quiet and peaceful. Large, secluded property. Good base from which to explore area wineries, local beer, food, and hike im the Shenandoah National Park."
United States
Steven
The price is AU$423
includes taxes & fees
14 Dec - 15 Dec
Mechum Hill Cottage: Central to Crozet & Cville

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, (4)
"Very good stay. Quiet and as advertised!"
United States
Robert B.
The price is AU$239
includes taxes & fees
17 Dec - 18 Dec
Brand new serene luxury cottage just off the Brew Ridge Trail

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (216)
"I liked the cleanliness of the suite, the fully staffed kitchen, the large bathroom, the comfortable bed, the ease and safety of the parking area."
United States
Tammy
The price is AU$191
includes taxes & fees
14 Dec - 15 Dec
Valley Extended Suites

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, (45)
"Lovely stay. Clean, comfortable, quaint, and roomy. Perfect location for our family!"
United States
kim E.
The price is AU$428
includes taxes & fees
14 Dec - 15 Dec
Unique Cypress cottage, close to Charlottesville with mountain views.

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Ivy
10.0 out of 10, Exceptional, (40)
"It was a lovely place to stay and the hosts were so kind. "
United States
Cooper C.
The price is AU$286
includes taxes & fees
15 Dec - 16 Dec
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (3)
"Love the area"
United States
Toni
The price is AU$586
includes taxes & fees
14 Dec - 15 Dec
Blackwood Chalet

The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
9.8 out of 10, Exceptional, (19)
"Great place"
United States
Beverly
The price is AU$478
includes taxes & fees
14 Dec - 15 Dec
The Cottage @ Afton Mountain- Close to Wineries!

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, (90)
"Great spot for a stay, hostess was amazing, highly recommend!!"
United States
Charles R.
The price is AU$298
includes taxes & fees
17 Dec - 18 Dec
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Afton
9.8 out of 10, Exceptional, (10)
"Very tranquil place. "
United States
Thomas K.
The price is AU$484
includes taxes & fees
14 Dec - 15 Dec
Afton Cottage w/ Hot Tub, Firepit, Mountain Views

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, (172)
"Gorgeous spot, and the cabin is very cozy and clean and has all the essentials, including smart TV and WiFi! Close to hiking trails, and not a far drive from wineries, breweries and a few restaurants. Sunsets are beautiful out back, and the location is quiet and peaceful."
United States
Lauren
The price is AU$263
includes taxes & fees
14 Dec - 15 Dec
Cozy cabin for 2 w/ great mt views & walking trails!

High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (104)
"reaturants walking distance, just wish the water pressure was better"
United States
ann l.
The price is AU$505
includes taxes & fees
14 Dec - 15 Dec
High Street | Walk to Everything Crozet | Pet-Friendly

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, (19)
"Beautiful home, very comfortable, and uniquely fun decor. Highly recommend!"
United States
Melissa
The price is AU$217
includes taxes & fees
14 Dec - 15 Dec
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

Hillside Haven: Modern Retreat, Mountain Views

Hillside Haven: Modern Retreat, Mountain Views
Faber
10.0 out of 10, Exceptional, (32)
"Fantastic property with all the amenities near UVA, and lots of wineries."
United States
roberto c.
The price is AU$577
includes taxes & fees
14 Dec - 15 Dec
Hillside Haven: Modern Retreat, Mountain Views

Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi

Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
Verona
10.0 out of 10, Exceptional, (58)
"Great place to stay. "
United States
Kelly H
The price is AU$356
includes taxes & fees
17 Dec - 18 Dec
Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi

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

NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Waynesboro
9.6 out of 10, Exceptional, (44)
"We enjoyed this cozy home during our annual trip to the area. Loved the charming, private backyard. Nearby vineyards and Blue Ridge Parkway were an added bonus. "
United States
Virginia W.
The price is AU$307
includes taxes & fees
15 Dec - 16 Dec
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
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, 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 favourite 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 depend 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 AU$191 per night. Entering your travel dates in the search wizard might find you 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?

Large and Luxurious Exec 5BR Chalet: This holiday home rental outside of Sherando is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 Raven's Roost Overlook 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.