Women In Travel - Vacation Rentals in Sherando

COZY SKI COTTAGE-SKI IN SKI OUT From US $304
         

9.6 (93 Reviews)
House
  • Air Conditioner
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  • TV
Dreamy Afton Cottage By Shenandoah Natl Park From US $189
         

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10.0 (1 Review)
House
  • Parking
  • Wheelchair Accessible
  • Child Friendly
Blackwood Chalet From US $380
         

10.0 (3 Reviews)
Cabin
  • Parking
  • Security/Safety
  • Spa
Blue Ridge Mountain Retreat in Wintergreen From US $692
         

Shenandoah Valley Farm House near BR pkway & Skyline , UVA, Staunton, wineries From US $325
         

10.0 (139 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Luxury Places to Stay in Sherando

Over 1463+ Luxury Places to Stay in or Near Sherando
Wintergreen Luxury, Best Views in VA! From US $2,254
         

10.0 (36 Reviews)
Ski Chalet
  • Air Conditioner
  • Parking
  • Pet Friendly
Dragon's Back, 9BR 10BA in Wintergreen From US $2,097
         

10.0 (6 Reviews)
Ski Chalet
  • Air Conditioner
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  • Pet Friendly
Wine Country Modern Farmhouse on 10 Acres and Pool From US $1,798
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Sherando

Over 862+ Top-Rated Vacation Rentals with a Pool in or Near Sherando
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes From US $156
         

Large and Luxurious Exec 5BR Chalet From US $496
         

10.0 (257 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Sherando

Over 416+ Pet-Friendly Vacation Rentals in or Near Sherando
Pets-OK Retreat w Sauna, Jacuzzi at Wintergreen From US $1,183
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Afton Mountain Vineyards From US $393
         

10.0 (1 Review)
Cabin
  • Parking
  • Pet Friendly
  • TV
Come and enjoy a beautiful view and relaxing time at Windy Knoll. From US $296
         

10.0 (223 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Spectacular Ski Chalet, 3 BR, 2.5 Bath, Great Location. From US $371
         

10.0 (121 Reviews)
Ski Chalet
  • Air Conditioner
  • Parking
  • Pet Friendly
Endless Mountain Top Views from All The Way Up! From US $254
         

10.0 (101 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Sherando on PetFriendly.io

Large Vacation Homes & Villas in Sherando

Over 319+ Large Vacation Homes & Villas in or Near Sherando
Unbeatable Views Atop Wintergreen Resort From US $718
         

10.0 (141 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Elegant Afton Getaway Near Trails and Vineyards From US $655
         

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New
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  • Wheelchair Accessible
  • Child Friendly
1 Mi to Slopes & Dining: Spacious Ski Getaway! From US $500
         

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14 From US $617
         

10.0 (61 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious + Serene Mtn Top Escape, 4 En Suites From US $296
         

10.0 (56 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Grand Chalet w/Hot Tub - Near Wintergreen Resort From US $671
         

Wheelchair Accessible Vacation Homes in Sherando

Over 33+ Wheelchair Accessible Vacation Homes in or Near Sherando
180 Degree Breathtaking Views From US $417
         

10.0 (19 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Iris Inn and Cabins From US $335
         

9.7 (3 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
The Farmhouse at Veritas From US $365
         

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9.8 (34 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV

Sherando Vacation Rentals and Airbnb Places to Stay Under $200

Over 260+ Sherando Vacation Rentals and Airbnb Places to Stay Under $200
Wintergreen Condo w/Pool: Near Hike & Market! From US $185
         

Wintergreen Resort Condo: Walk to Ski Lift! From US $200
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Ski-In/Ski-Out Comfy Condo From US $137
         

10.0 (38 Reviews)
Condo
  • Air Conditioner
  • TV
  • Security/Safety
Afton escape centrally located on the brew trail From US $187
         

10.0 (36 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Nona's Cottage-Waynesboro/Shenandoah Valley, VA From US $150
         

Wintergreen Resort Vacation Rental w/Balcony! From US $150
         

10.0 (17 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Sherando

Over 759+ Instantly Bookable Vacation Homes in or Near Sherando
Cozy Escape w/Sunrise Views, Pizza & Breweries From US $274
         

10.0 (76 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

About Sherando Vacation Rentals

With more than 1472 Sherando vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Womenintravel and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Sherando.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Womenintravel Sherando, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Sherando. Places to stay near Sherando are 1196.35 ft² on average, with prices averaging US $401 a night.

Womenintravel makes it easy and safe to find and compare vacation rentals in Sherando with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Sherando

Type Count
Vacation Homes 721
Cabin Rentals 81
Holiday Apartments 78
Cottages 32
Ski Chalet Rentals 27
Hotels 18
Others 2
Resorts 2
B&B 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Sherando

Pro Tip: Womenintravel makes it easy to compare the best listings on Womenintravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Womenintravel homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Sherando.

Weather in Sherando

View the weather forecast for Sherando before booking your Sherando Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Sherando Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Sherando?
How many vacation rentals are available in Sherando?

Currently, the total number of properties listed in 2026 is over 1472 in the Sherando area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Sherando.