Sherando Holiday Rentals
Condo
- Charlottesville
- ·
- Nellysford
- 2.88 mi to center
10.0Exceptional
(174 Reviews)
2 Bedrooms
2 Baths
6 Guests
Parking
Pool
Skiing
Balcony/Terrace
CA $331/Night
7 Nights - CA $2,316
House
10.0Exceptional
(3 Reviews)
4 Bedrooms
3 Baths
11 Guests
2895.49 ft²
EV Charge Station- Parking
View
Air Conditioner
CA $882/Night
7 Nights - CA $6,173
CA $673/Night
7 Nights - CA $4,711
Condo
- Charlottesville
- ·
- Wintergreen
- 1.73 mi to center
10.0Exceptional
(156 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Pool
Ocean View- Balcony/Terrace
CA $357/Night
7 Nights - CA $2,498
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
5 Baths
14 Guests
5500.36 ft²
Oceanfront
Hot Tub- Parking
- Pool
CA $2,501/Night
7 Nights - CA $17,506
Apartment
10.0Exceptional
(151 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $294/Night
7 Nights - CA $2,061
Condo
- Charlottesville
- ·
- Nellysford
- 2.97 mi to center
10.0Exceptional
(122 Reviews)
2 Bedrooms
2 Baths
5 Guests
1000 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $379/Night
7 Nights - CA $2,651
Condo
- Charlottesville
- ·
- Nellysford
- 2.90 mi to center
10.0Exceptional
(119 Reviews)
2 Bedrooms
2 Baths
5 Guests
1100 ft²
- Parking
- Pool
- Balcony/Terrace
Kitchen
CA $428/Night
7 Nights - CA $2,999
Condo
- Charlottesville
- ·
- Chestnut Springs
- 0.33 mi to center
10.0Exceptional
(91 Reviews)
2 Bedrooms
2 Baths
5 Guests
1237 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $412/Night
7 Nights - CA $2,886
Luxury Holiday Rentals in Sherando
Over 1534+ Luxury Holiday Rentals in or Near Sherando
New
House
- Charlottesville
- ·
- Roseland
- 8.16 mi to center
6 Bedrooms
6 Baths
20 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
Unlock the Best Price
House
- Charlottesville
- ·
- Nellysford
- 3.55 mi to center
10.0Exceptional
(1 Review)
9 Bedrooms
9 Baths
18 Guests
7844 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $3,575/Night
7 Nights - CA $25,024
House
- Charlottesville
- ·
- Chestnut Springs
- 0.35 mi to center
8.0Excellent
(1 Review)
10 Bedrooms
10 Baths
20 Guests
7644 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $3,501/Night
7 Nights - CA $24,507
House
- Charlottesville
- ·
- Chestnut Springs
- 0.35 mi to center
10 Bedrooms
10 Baths
20 Guests
7642.38 ft²
- Parking
- Pool
- Spa
- Skiing
CA $3,483/Night
7 Nights - CA $24,380
House
- Charlottesville
- ·
- Nellysford
- 3.55 mi to center
9 Bedrooms
9 Baths
18 Guests
7846.89 ft²
- Parking
- Pool
- Spa
- Skiing
CA $3,279/Night
7 Nights - CA $22,955
Ski Chalet
- Charlottesville
- ·
- Nellysford
- 3.61 mi to center
10.0Exceptional
(8 Reviews)
9 Bedrooms
10 Baths
18 Guests
6200 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $3,040/Night
7 Nights - CA $21,277
House
- Charlottesville
- ·
- Nellysford
- 2.94 mi to center
10.0Exceptional
(11 Reviews)
6 Bedrooms
4 Baths
16 Guests
- Hot Tub
- Parking
- Pool
- Spa
CA $2,740/Night
7 Nights - CA $19,178
House
10.0Exceptional
(7 Reviews)
5 Bedrooms
1 Bath
16 Guests
- Pool
- Balcony/Terrace
- Kitchen
Internet
CA $2,500/Night
7 Nights - CA $17,501
House
- Charlottesville
- ·
- Roseland
- 8.91 mi to center
10.0Exceptional
(44 Reviews)
7 Bedrooms
9 Baths
18 Guests
7700 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $2,246/Night
7 Nights - CA $15,723
Top-Rated Holiday Rentals with a Pool in Sherando
Over 879+ The Best Private Villas and Holiday Rentals in Sherando with a Pool
House
- Charlottesville
- ·
- Pedlars Edge
- 0.14 mi to center
10.0Exceptional
(258 Reviews)
5 Bedrooms
4 Baths
10 Guests
- Parking
- Pool
- Skiing
- Balcony/Terrace
CA $781/Night
7 Nights - CA $5,468
House
- Charlottesville
- ·
- Nellysford
- 3.00 mi to center
10.0Exceptional
(223 Reviews)
6 Bedrooms
4 Baths
16 Guests
3800 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $1,515/Night
7 Nights - CA $10,606
House
- Charlottesville
- ·
- Nellysford
- 3.43 mi to center
10.0Exceptional
(112 Reviews)
4 Bedrooms
3 Baths
10 Guests
2750 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $595/Night
7 Nights - CA $4,167
Condo
- Charlottesville
- ·
- Wintergreen
- 1.79 mi to center
10.0Exceptional
(88 Reviews)
2 Bedrooms
2 Baths
6 Guests
972 ft²
Private Pool- Parking
- Pool
- Balcony/Terrace
CA $442/Night
7 Nights - CA $3,095
Condo
- Charlottesville
- ·
- Chestnut Springs
- 0.28 mi to center
10.0Exceptional
(86 Reviews)
2 Bedrooms
2 Baths
6 Guests
1179 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $451/Night
7 Nights - CA $3,155
House
- Charlottesville
- ·
- Laurel Ridge
- 0.14 mi to center
10.0Exceptional
(78 Reviews)
3 Bedrooms
2 Baths
8 Guests
1600 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $623/Night
7 Nights - CA $4,363
House
- Charlottesville
- ·
- Chestnut Springs
- 0.24 mi to center
10.0Exceptional
(77 Reviews)
4 Bedrooms
3 Baths
6 Guests
2600 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $1,160/Night
7 Nights - CA $8,116
New
Condo
- Charlottesville
- ·
- Nellysford
- 3.05 mi to center
10.0Exceptional
(76 Reviews)
2 Bedrooms
2 Baths
6 Guests
1370 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $466/Night
7 Nights - CA $3,262
House
- Charlottesville
- ·
- Deer Springs
- 0.07 mi to center
10.0Exceptional
(75 Reviews)
3 Bedrooms
2 Baths
6 Guests
1300 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $429/Night
7 Nights - CA $3,002
Pet-Friendly Holiday Rentals in Sherando
Over 461+ Pet-Friendly Holiday Rentals in or Near Sherando
Condo
- Charlottesville
- ·
- Nellysford
- 2.90 mi to center
10.0Exceptional
(52 Reviews)
2 Bedrooms
2 Baths
6 Guests
1150 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $446/Night
7 Nights - CA $3,121
House
- Charlottesville
- ·
- Treeloft
- 0.10 mi to center
10.0Exceptional
(2 Reviews)
8 Bedrooms
8 Baths
28 Guests
21151.08 ft²
- Hot Tub
Breakfast- Parking
- Spa
CA $1,282/Night
7 Nights - CA $8,974
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Internet
Pet Friendly
CA $826/Night
7 Nights - CA $5,784
Condo
- Charlottesville
- ·
- Nellysford
- 3.29 mi to center
10.0Exceptional
(49 Reviews)
1 Bedroom
1 Bath
4 Guests
615 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $291/Night
7 Nights - CA $2,034
House
- Charlottesville
- ·
- Chestnut Springs
- 0.31 mi to center
10.0Exceptional
(2 Reviews)
6 Bedrooms
4 Baths
12 Guests
2583.34 ft²
- Parking
- Internet
- Pet Friendly
Child Friendly
CA $712/Night
7 Nights - CA $4,982
House
- Charlottesville
- ·
- Wintergreen
- 1.50 mi to center
10.0Exceptional
(32 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $498/Night
7 Nights - CA $3,484
House
10.0Exceptional
(17 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $722/Night
7 Nights - CA $5,052
Condo
- Charlottesville
- ·
- Wintergreen
- 1.75 mi to center
10.0Exceptional
(17 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $401/Night
7 Nights - CA $2,810
Condo
- Charlottesville
- ·
- Nellysford
- 3.18 mi to center
10.0Exceptional
(17 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $301/Night
7 Nights - CA $2,104
Large Holiday Rentals and Private Villas in Sherando
Over 331+ Large Holiday Rentals and Private Villas in or Near Sherando
House
- Charlottesville
- ·
- Nellysford
- 3.35 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
10 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $418/Night
7 Nights - CA $2,927
Ski Chalet
- Charlottesville
- ·
- Treeloft
- 0.09 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
1797.57 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $384/Night
7 Nights - CA $2,687
Ski Chalet
- Charlottesville
- ·
- Wintergreen
- 0.99 mi to center
6 Bedrooms
5 Baths
16 Guests
5000 ft²
- Hot Tub
- Parking
- Pool
- Spa
CA $2,057/Night
7 Nights - CA $14,399
New
Cabin
- Charlottesville
- ·
- Chestnut Springs
- 0.10 mi to center
3 Bedrooms
3 Baths
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
CA $545/Night
7 Nights - CA $3,818
House
- Charlottesville
- ·
- Nellysford
- 3.00 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
12 Guests
2873.96 ft²
- Hot Tub
- Parking
- Spa
- Internet
CA $1,413/Night
7 Nights - CA $9,892
House
- Charlottesville
- ·
- Roseland
- 8.46 mi to center
10.0Exceptional
(146 Reviews)
5 Bedrooms
3 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $1,040/Night
7 Nights - CA $7,277
House
- Charlottesville
- ·
- Nellysford
- 3.21 mi to center
10.0Exceptional
(132 Reviews)
4 Bedrooms
3 Baths
10 Guests
2847 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
CA $746/Night
7 Nights - CA $5,222
House
- Charlottesville
- ·
- Roseland
- 8.94 mi to center
10.0Exceptional
(71 Reviews)
5 Bedrooms
4 Baths
10 Guests
3300 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $838/Night
7 Nights - CA $5,866
House
- Charlottesville
- ·
- Nellysford
- 3.43 mi to center
10.0Exceptional
(68 Reviews)
5 Bedrooms
3 Baths
14 Guests
3000 ft²
- Hot Tub
- Parking
- Pool
- Spa
CA $656/Night
7 Nights - CA $4,591
Wheelchair Accessible Holiday Homes in Sherando
Over 32+ Wheelchair Accessible Holiday Homes in or Near Sherando
Condo
- Charlottesville
- ·
- Chestnut Springs
- 0.25 mi to center
2 Bedrooms
2 Baths
4 Guests
1136 ft²
- Hot Tub
- Parking
- Pool
- Kitchen
CA $706/Night
7 Nights - CA $4,941
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
1539.24 ft²
- Parking
- Internet
- Child Friendly
Wheelchair Accessible
CA $263/Night
7 Nights - CA $1,840
Bed & Breakfast
9.8Exceptional
(36 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
CA $538/Night
7 Nights - CA $3,765
Condo
- Charlottesville
- ·
- Chestnut Springs
- 0.26 mi to center
1 Bedroom
1 Bath
2 Guests
1136 ft²
- Hot Tub
- Parking
- Pool
- Kitchen
CA $500/Night
7 Nights - CA $3,502
Resort
- Staunton
- ·
- Waynesboro
- 3.63 mi to center
9.7Exceptional
(3 Reviews)
7 Baths
16 Guests
395.19 ft²
- Hot Tub
- Breakfast
- EV Charge Station
- Parking
CA $621/Night
7 Nights - CA $4,348
New
Condo
- Charlottesville
- ·
- Chestnut Springs
- 0.23 mi to center
2 Bedrooms
2 Baths
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $348/Night
7 Nights - CA $2,438
Condo
- Charlottesville
- ·
- Chestnut Springs
- 0.16 mi to center
10.0Exceptional
(19 Reviews)
3 Bedrooms
3 Baths
6 Guests
1650 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $762/Night
7 Nights - CA $5,333
House
9.6Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
9 Guests
2596 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $698/Night
7 Nights - CA $4,886
Condo
- Charlottesville
- ·
- Chestnut Springs
- 0.28 mi to center
3 Bedrooms
3 Baths
6 Guests
1483 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $928/Night
7 Nights - CA $6,498
Sherando Private Villas and Holiday Homes Under $200
Over 246+ Sherando Private Villas and Holiday Homes Under $200
Condo
- Charlottesville
- ·
- Nellysford
- 2.58 mi to center
10.0Exceptional
(40 Reviews)
1 Bedroom
1 Bath
4 Guests
- Skiing
- Kitchen
- Air Conditioner
- Internet
CA $241/Night
7 Nights - CA $1,684
House
- Charlottesville
- ·
- Wintergreen
- 1.75 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
936.46 ft²
- Parking
- Pool
- Balcony/Terrace
- Internet
CA $238/Night
7 Nights - CA $1,666
Apartment
- Charlottesville
- ·
- Nellysford
- 3.05 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
- Parking
- Pool
- Kitchen
- Air Conditioner
CA $278/Night
7 Nights - CA $1,947
Condo
- Charlottesville
- ·
- Wintergreen
- 1.74 mi to center
10.0Exceptional
(13 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $272/Night
7 Nights - CA $1,903
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
6 Guests
1345.49 ft²
- Parking
- Internet
- Child Friendly
Sports/Activities
CA $230/Night
7 Nights - CA $1,607
Condo
- Charlottesville
- ·
- Wintergreen
- 1.71 mi to center
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $262/Night
7 Nights - CA $1,837
House
- Charlottesville
- ·
- Nellysford
- 2.96 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $272/Night
7 Nights - CA $1,903
Condo
- Charlottesville
- ·
- Chestnut Springs
- 0.23 mi to center
9.8Exceptional
(124 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $275/Night
7 Nights - CA $1,925
Condo
- Charlottesville
- ·
- Nellysford
- 2.43 mi to center
9.8Exceptional
(85 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $266/Night
7 Nights - CA $1,864
Instantly Bookable Holiday Homes in Sherando
Over 798+ Instantly Bookable Holiday Homes in or Near Sherando
Cottage
10.0Exceptional
(66 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $347/Night
7 Nights - CA $2,429
House
- Charlottesville
- ·
- Nellysford
- 3.39 mi to center
9.4Exceptional
(15 Reviews)
3 Bedrooms
2 Baths
9 Guests
1847 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $491/Night
7 Nights - CA $3,438
Condo
- Charlottesville
- ·
- Nellysford
- 2.97 mi to center
10.0Exceptional
(42 Reviews)
2 Bedrooms
2 Baths
5 Guests
1100 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $439/Night
7 Nights - CA $3,074
Condo
- Charlottesville
- ·
- Wintergreen
- 2.00 mi to center
10.0Exceptional
(42 Reviews)
2 Bedrooms
2 Baths
5 Guests
907 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $435/Night
7 Nights - CA $3,045
House
10.0Exceptional
(42 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $288/Night
7 Nights - CA $2,017
Condo
- Charlottesville
- ·
- Wintergreen
- 1.93 mi to center
10.0Exceptional
(39 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Parking
- Skiing
- Balcony/Terrace
- Kitchen
CA $568/Night
7 Nights - CA $3,978
Condo
- Charlottesville
- ·
- Nellysford
- 3.05 mi to center
10.0Exceptional
(24 Reviews)
2 Bedrooms
2 Baths
6 Guests
1126 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $426/Night
7 Nights - CA $2,985
Condo
- Charlottesville
- ·
- Nellysford
- 2.72 mi to center
10.0Exceptional
(22 Reviews)
2 Bedrooms
2 Baths
8 Guests
1140 ft²
- Parking
- Pool
- Skiing
- Balcony/Terrace
CA $316/Night
7 Nights - CA $2,210
Condo
- Charlottesville
- ·
- Wintergreen
- 1.96 mi to center
10.0Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Parking
- Pool
- Skiing
- Balcony/Terrace
CA $344/Night
7 Nights - CA $2,405
Book a Last Minute Place to Stay in Sherando
About Casai's Private Villas and Holiday Rentals in Sherando
Discover more than 1543 vacation rentals available in Sherando. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Sherando.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Sherando, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Sherando. On average, places to stay near Sherando offer 1164.14 ft², with nightly prices averaging CA $598.
With Casai, finding and comparing holiday rentals in Sherando is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Sherando
| Type | Count |
|---|---|
| Vacation Homes | 765 |
| Holiday Apartments | 103 |
| Cottages | 32 |
| Villas | 1 |
Use these Quick Filters to Find a Holiday Rental in Sherando
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Sherando.
Weather in Sherando, VA
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
Top Attractions Around Sherando, VA
Casai offers a large selection of top attractions around Sherando . Research things to do on your vacation before you visit Sherando.
Frequently Asked Questions About Sherando?
What are the top holiday rentals in Sherando?
With numerous options available in Sherando, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Sherando:
- Large and Luxurious Exec 5BR Chalet
- Reconnect with family & friends at our large, private, stylish Wintergreen home
- Highlands Condo Views for days! Tons of details listed ⬇️☺️
- Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.
- Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries.
- Unbeatable Views Atop Wintergreen Resort
- Shenandoah Valley Farm House near BR pkway & Skyline , UVA, Staunton, wineries
- Calm Creek Retreat - minutes from slopes, hot tub, large cozy family room!
- Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
- Endless Mountain Top Views from All The Way Up!
How many holiday rentals have private pools in Sherando?
Discover a selection of holiday rentals with private pools near Sherando with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Overlook 180 degree views w/Peloton!
- Holiday Inn Express & Suites Waynesboro East
- Escape to Wintergreen Resort! Our pet & kid-friendly 2BR/2BA townhome is steps from skiing, dining & the Market. Hike, ski, swim, or sip at nearby wineries & breweries—adventure awaits year-round!
- One of the Best Views in Wintergreen!
Which holiday homes in Sherando are best for families?
If you're searching for a family-friendly holiday home in Sherando, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Sherando:
- Buena Vista - Your Panoramic Retreat - Million Dollar View
- Timbers Studio 48 With Wintergreen Advantage
- Blackwood Chalet
How many Casai.ca holiday rentals are available in Sherando?
As of 2026, Casai boasts over 1543 properties listed in the Sherando area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Sherando.
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