Best Vacation Homes in Sherando
Condo
10.0(197 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
Skiing
Fireplace/Heating
Pool
Balcony/Terrace
US $267/Night
7 Nights - US $1,872
House
10.0(3 Reviews)
4 Bedrooms
3 Baths
11 Guests
2895.49 ft²
- Fireplace/Heating
View
Parking
Air Conditioner
US $1,010/Night
7 Nights - US $7,070
US $438/Night
7 Nights - US $3,066
Condo
10.0(168 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Skiing
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $276/Night
7 Nights - US $1,934
House
10.0(2 Reviews)
5 Bedrooms
5 Baths
14 Guests
5500.36 ft²
Oceanfront
Hot Tub- Pool
Ocean View
US $1,798/Night
7 Nights - US $12,586
Condo
10.0(155 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $257/Night
7 Nights - US $1,796
Apartment
10.0(147 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $212/Night
7 Nights - US $1,482
Condo
10.0(118 Reviews)
2 Bedrooms
2 Baths
5 Guests
1000 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $309/Night
7 Nights - US $2,162
Sherando Luxury Rentals
House
10 Bedrooms
10 Baths
20 Guests
7642.38 ft²
- Skiing
- Pool
- Balcony/Terrace
- Parking
US $2,504/Night
7 Nights - US $17,528
House
9 Bedrooms
9 Baths
18 Guests
7846.89 ft²
- Skiing
- Pool
- Parking
- Air Conditioner
US $2,358/Night
7 Nights - US $16,503
House
8.0(1 Review)
10 Bedrooms
10 Baths
20 Guests
7644 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $2,279/Night
7 Nights - US $15,954
House
9 Bedrooms
9 Baths
18 Guests
7844 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $2,164/Night
7 Nights - US $15,148
Ski Chalet
10.0(7 Reviews)
9 Bedrooms
10 Baths
18 Guests
6200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
Pet Friendly
US $2,082/Night
7 Nights - US $14,576
House
10.0(7 Reviews)
5 Bedrooms
1 Bath
16 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
Kitchen
US $2,032/Night
7 Nights - US $14,224
House
10.0(1 Review)
5 Bedrooms
4 Baths
13 Guests
21528 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,694/Night
7 Nights - US $11,859
House
10.0(43 Reviews)
7 Bedrooms
9 Baths
18 Guests
7700 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,558/Night
7 Nights - US $10,907
Sherando Pet Friendly Vacation Rentals
Condo
10.0(105 Reviews)
2 Bedrooms
2 Baths
5 Guests
1100 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $293/Night
7 Nights - US $2,051
House
10.0(2 Reviews)
8 Bedrooms
8 Baths
28 Guests
21151.08 ft²
- Hot Tub
Spa- Skiing
- Fireplace/Heating
US $1,183/Night
7 Nights - US $8,279
Apartment
9.4(3 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $193/Night
7 Nights - US $1,351
Condo
10.0(88 Reviews)
2 Bedrooms
2 Baths
6 Guests
972 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
US $318/Night
7 Nights - US $2,225
House
10.0(2 Reviews)
6 Bedrooms
4 Baths
12 Guests
2583.34 ft²
- Pet Friendly
- Parking
Internet
Child Friendly
US $398/Night
7 Nights - US $2,786
Condo
10.0(82 Reviews)
2 Bedrooms
2 Baths
6 Guests
1179 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $337/Night
7 Nights - US $2,358
Condo
10.0(76 Reviews)
2 Bedrooms
2 Baths
6 Guests
1370 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $315/Night
7 Nights - US $2,203
Condo
10.0(50 Reviews)
2 Bedrooms
2 Baths
6 Guests
1150 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $312/Night
7 Nights - US $2,185
Sherando Large Vacation Homes
House
10.0(4 Reviews)
1 Bedroom
1 Bath
10 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $301/Night
7 Nights - US $2,104
Ski Chalet
10.0(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
1797.57 ft²
- Kitchen
- Parking
- Air Conditioner
- Internet
US $276/Night
7 Nights - US $1,932
Ski Chalet
6 Bedrooms
5 Baths
16 Guests
5000 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $1,479/Night
7 Nights - US $10,352
House
10.0(70 Reviews)
5 Bedrooms
4 Baths
10 Guests
3300 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $627/Night
7 Nights - US $4,389
House
10.0(1 Review)
4 Bedrooms
3 Baths
12 Guests
2873.96 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Parking
US $750/Night
7 Nights - US $5,248
New
House
10.0(54 Reviews)
4 Bedrooms
3 Baths
12 Guests
2876 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $935/Night
7 Nights - US $6,546
Cabin
10.0(24 Reviews)
5 Bedrooms
3 Baths
12 Guests
3300 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $513/Night
7 Nights - US $3,589
New
Condo
10.0(19 Reviews)
4 Bedrooms
2 Baths
15 Guests
1443 ft²
- Skiing
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $399/Night
7 Nights - US $2,793
Why Choose Rent By Owner for your Sherando Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Sherando
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience and help you make the most of your stay in this charming destination within the region.
Peak Season Highlights
Spring (March to May)
During spring, this region experiences mild temperatures and blooming landscapes, making it an ideal time to explore the scenic beauty while staying in comfortable vacation rentals.
Average Temperature Daytime: 60-75°F - Nighttime: 40-55°F
Fall (September to November)
In fall, the vibrant foliage creates a picturesque setting, attracting visitors who seek cozy accommodations and outdoor excursions amid colorful scenery.
Average Temperature Daytime: 55-70°F - Nighttime: 35-50°F
Off-Season Highlights
Summer (June to August)
Summertime offers warm weather perfect for outdoor activities, though this is also the busiest season, so early booking of vacation rentals is recommended to secure the best options.
Average Temperature Daytime: 80-90°F - Nighttime: 60-65°F
Winter (December to February)
Winter presents cooler temperatures and fewer visitors, providing a peaceful retreat with potential for seasonal festivities and scenic snowy views from your vacation rental.
Average Temperature Daytime: 40-50°F - Nighttime: 25-35°F
Weekly Weather Forecast for Sherando
How to Book Your Sherando Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Sherando
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining on a private patio or deck, perfect for relaxing after exploring the region.
- Take advantage of spacious yards ideal for outdoor games and family activities amidst scenic surroundings.
- Relax by a crackling outdoor fireplace or fire pit during cooler evenings in this destination’s serene setting.
- Make the most of a pool or hot tub to unwind while soaking up views of the natural landscape.
- Explore nearby hiking or walking trails accessible directly from your rental in this area.
- Utilize outdoor grills available at many properties for a cookout in the fresh air.
- Park your boat or enjoy water-based activities if your rental offers direct access to nearby lakes or rivers.
Top Attractions Around Sherando
What attractions are nearby?
Discover a variety of outdoor activities, scenic trails, and charming local attractions nearby to enhance your stay in this region, offering you an authentic experience of the area’s natural beauty and cultural charm.
Family Activities
- Sherando Lake Recreation Area: Enjoy a family day outdoors by exploring the scenic trails, swimming, and picnicking in this popular natural spot near the region.
- Virginia Safari Park: Experience an exciting drive-through safari adventure where your family can see exotic animals in a naturalistic setting just a short drive from here.
- Historic Ash Lawn-Highland: Discover the rich history of Thomas Jefferson’s beloved estate, offering educational tours and family-friendly events throughout the year.
- Lyndhurst Park: Relax and play at this local park featuring playgrounds, walking trails, and open spaces perfect for a family outing in the area.
Adult Activities
- Hiking in Shenandoah National Park: Explore the scenic trails nearby that offer breathtaking views and an opportunity to connect with nature.
Sherando Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Outdoor Activities: Take advantage of the scenic natural surroundings by planning outdoor adventures like hiking or biking to truly experience this destination's beautiful landscape.
- Visit Nearby Natural Landmarks: Discover the region’s natural landmarks to enjoy tranquil views and connect with nature during your stay in this area.
- Start Your Day with a Morning Walk: Beginning your day with a walk around the neighborhood or nearby parks helps you immerse yourself in the local atmosphere and scenery.
- Choose a Well-Located Vacation Rental: Select a property close to key outdoor spots to maximize your time exploring the area's natural beauty and amenities.
Transportation Options
- Rental Car Services: Locally available car rental agencies offer convenient options to explore the region at your own pace, ideal for reaching scenic spots and outdoor adventures around this destination.
- Public Transportation: Bus services in the area provide budget-friendly and reliable transportation, connecting you to nearby towns and essential points of interest within Lyndhurst and beyond.
- Taxi and Ride-Sharing: Taxis and ride-sharing services are readily accessible here, offering quick and comfortable transport options for short trips or airport pickups.
- Private Shuttle Services: Private shuttle providers operate in the region, providing flexible routes tailored to your schedule, perfect for exploring local attractions conveniently.
Local Customs Options
- Southern Hospitality: In this part of Virginia, you'll notice a warm and welcoming attitude that embodies traditional southern hospitality, making your stay feel like a true home away from home.
- Local Folk Art and Craftsmanship: The area is known for its vibrant local arts scene, where handcrafted items often reflect the region's rich cultural heritage and are celebrated in community events.
- Respect for Nature and Outdoor Traditions: Here, outdoor activities such as hiking and fishing are deeply rooted in local customs, and visitors are encouraged to honor the natural landscape.
- Community Gatherings and Festivals: Throughout the year, you'll find that community festivals and gatherings play an important role in bringing residents together to celebrate regional traditions and history.
Sherando Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Sherando?
There are a lot of options in Sherando. If you plan on staying in the Sherando area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Sherando:
- Large and Luxurious Exec 5BR Chalet
- Reconnect with family & friends at our large, private, stylish Wintergreen home
- Cozy Mountain vibes @ Dobie condos, - location location location!
- Book Now for Spring and Summer.Awesome Views and 5-Star Amenities
- Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!
- Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.
- Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries.
- Custom Builder just completely remodeled this Mountain Chalet! .with Hot Tub!
- Unbeatable Views Atop Wintergreen Resort
- Shenandoah Valley Farm House near BR pkway & Skyline , UVA, Staunton, wineries
2. How many vacation rentals have private pools in Sherando?
There are 23 vacation rentals with private pools near Sherando. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Sherando are best for families?
If you are looking for a family-friendly vacation home in Sherando, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Sherando:
4. How many Rentbyowner vacation rentals are available in Sherando?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1495 in the Sherando area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Sherando.
5. What is the cancellation policy for vacation rentals in Sherando, Lyndhurst, Virginia?
Cancellation policies vary depending on the property listing. You should review the specific rental's cancellation terms on the listing page or contact the property owner directly for detailed information.
6. How do I confirm my reservation at a vacation rental here?
Reservation confirmation typically occurs once you complete the booking process and receive a confirmation email from the host. Be sure to read the listing details for any special instructions or requirements.
7. Are there any fees associated with booking a vacation rental in this region?
Additional fees such as cleaning fees, service charges, or taxes may apply. These will be clearly outlined during the booking process or on the final invoice, so review the details before confirming your reservation.
8. Can I modify or cancel my stay after booking a vacation rental?
Modifications and cancellations are subject to the property's policy. Check the specific listing for rules regarding changes or cancellations, or contact the owner directly for assistance.
9. What amenities are typically included in vacation rentals near Lyndhurst, Virginia?
Amenities can vary by property, but many rentals often include essentials like Wi-Fi, parking, and kitchen facilities. To find out about specific amenities, review each listing thoroughly or reach out directly to the host.
Sherando Top Rated Vacation Rentals
House
10.0(258 Reviews)
5 Bedrooms
4 Baths
10 Guests
- Skiing
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $562/Night
7 Nights - US $3,931
House
10.0(223 Reviews)
6 Bedrooms
4 Baths
16 Guests
3800 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $1,073/Night
7 Nights - US $7,511
Condo
10.0(186 Reviews)
3 Bedrooms
3 Baths
8 Guests
1610 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $466/Night
7 Nights - US $3,262
House
10.0(135 Reviews)
5 Bedrooms
5 Baths
12 Guests
4000 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $999/Night
7 Nights - US $6,994
Ski Chalet
10.0(122 Reviews)
3 Bedrooms
2 Baths
8 Guests
1900 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $481/Night
7 Nights - US $3,368
House
10.0(109 Reviews)
4 Bedrooms
3 Baths
10 Guests
2750 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $428/Night
7 Nights - US $2,996
House
10.0(76 Reviews)
4 Bedrooms
3 Baths
6 Guests
2600 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $834/Night
7 Nights - US $5,835
House
10.0(76 Reviews)
3 Bedrooms
2 Baths
8 Guests
1600 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $437/Night
7 Nights - US $3,058
