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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Sherando Vacation Homes

Farmhouse at the foot of the Blue Ridge Mountains
Terrace/patio

Farmhouse at the foot of the Blue Ridge Mountains

10.0 out of 10, Exceptional, (24)
"This is a very comfortable, wonderfully quiet place. Excellent spot for a family. "
The price is CA $254
CA $358 total
includes taxes & fees
Aug 21 - Aug 22
Farmhouse at the foot of the Blue Ridge Mountains
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Property grounds

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

10.0 out of 10, Exceptional, (243)
"Thanks for a wonderful stay at your beautiful farm! Great location for visiting wineries and Charlottesville."
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Upscale and Family-Friendly in Wintergreen
Indoor spa tub

Upscale and Family-Friendly in Wintergreen

9.8 out of 10, Exceptional, (23)
"We absolutely loved our stay. Great hiking access point and very family/pet friendly. Would love to come stay again!"
Upscale and Family-Friendly in Wintergreen
The Firefly Springhouse
Exterior

The Firefly Springhouse

10.0 out of 10, Exceptional, (31)
"The cottage was cute and the host was very friendly and helpful. The perfect place to stay for a couple nights."
The price is CA $114
CA $158 total
includes taxes & fees
Aug 24 - Aug 25
The Firefly Springhouse
Mountaintop Wintergreen Resort Home w/ Deck, Views
Interior

Mountaintop Wintergreen Resort Home w/ Deck, Views

9.8 out of 10, Exceptional, (53)
"Second time staying here and we had the best time. Great for a weekend getaway to hang out with friends and family. "
Mountaintop Wintergreen Resort Home w/ Deck, Views
NEW! Secluded Farmhouse + Solar Heated Pool + Firepit
Exterior

NEW! Secluded Farmhouse + Solar Heated Pool + Firepit

10.0 out of 10, Exceptional, (25)
"We had a great time. Very pretty house in a very pretty setting!"
NEW! Secluded Farmhouse + Solar Heated Pool + Firepit
White Rock Cabin
Fridge, microwave, oven, stovetop

White Rock Cabin

10.0 out of 10, Exceptional, (208)
"Above and beyond on everything highly recommend staying here"
White Rock Cabin
Newtown Retreat: Award-Winning Renovation + Ideal Location
Fridge, microwave, oven, stovetop

Newtown Retreat: Award-Winning Renovation + Ideal Location

10.0 out of 10, Exceptional, (28)
"This was a great place with a great location! 10/10 would stay here again."
Newtown Retreat: Award-Winning Renovation + Ideal Location
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop
Smart TV, fireplace, video games, DVD player

Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

10.0 out of 10, Exceptional, (295)
"The house was perfect for us. Plenty of space for everyone to hang out together. "
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop
The All-American Cottage Seconds from Gypsy Hill Park! Kid and Pet friendly!
Fridge, microwave, oven, stovetop

The All-American Cottage Seconds from Gypsy Hill Park! Kid and Pet friendly!

10.0 out of 10, Exceptional, (19)
"Such a great property and the owners are great! The house is super close to everything and the neighborhood is great. We can’t wait to book again! "
The All-American Cottage Seconds from Gypsy Hill Park! Kid and Pet friendly!
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
Outdoor spa tub

Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!

10.0 out of 10, Exceptional, (46)
"Check-in process was a breeze, communication with the hosts was super easy and consistent. Place was very clean and exactly as appears in the pictures. My group had an amazing time and loved the location of this property. Would 110% stay here again!"
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
Charming 3-bedroom house, breweries! hiking! wineries! scenic routes! Fishing!
Private kitchen

Charming 3-bedroom house, breweries! hiking! wineries! scenic routes! Fishing!

10.0 out of 10, Exceptional, (2)
"We traveled to VA from NY. Check in was easy and simple. As was checkout. It was conveniently located to a lot of places. Would stay again "
Charming 3-bedroom house, breweries! hiking! wineries! scenic routes! Fishing!
Cooler in the mountains, with hot tub.
Property grounds

Cooler in the mountains, with hot tub.

9.8 out of 10, Exceptional, (66)
"House was perfect for a weekend of skiing. You’re able to walk to the resort from the house which was a huge plus since it was a packed weekend. Overall great stay! "
Cooler in the mountains, with hot tub.
Hot Tub Mntn Views Pool Tennis Golf Hiking 52"HDTV
Terrace/patio

Hot Tub Mntn Views Pool Tennis Golf Hiking 52"HDTV

9.4 out of 10, Exceptional, (3)
"The property was well stocked and the location was excellent. There was plenty of firewood for the fireplace and the hot tub was perfect after a long day of skiing at the resort. "
Hot Tub Mntn Views Pool Tennis Golf Hiking 52"HDTV
Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!
Fridge, microwave, oven, stovetop

Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!

9.8 out of 10, Exceptional, (42)
"Beautiful property and very responsive host. Nice place to stay. "
The price is CA $223
CA $414 total
includes taxes & fees
Aug 21 - Aug 22
Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia
Property grounds

Bud's Place, Southern Charm in the Shenandoah Valley of Virginia

10.0 out of 10, Exceptional, (33)
"Loved the home! Was a perfect experience for us."
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia
Thrilling Views HotTub Sauna Gym EV Charger DogOK
Interior

Thrilling Views HotTub Sauna Gym EV Charger DogOK

10.0 out of 10, Exceptional, (1)
"Beautiful place! Amazing views! Great hospitality! Has everything you need! Plenty of amenities. Host provided everything we needed. "
Thrilling Views HotTub Sauna Gym EV Charger DogOK
Modern Luxury Mountain Home within Wintergreen Retreat Collection
Smart TV, fireplace, video games, video library

Modern Luxury Mountain Home within Wintergreen Retreat Collection

9.8 out of 10, Exceptional, (50)
"Perfect place to relax and enjoy the company of friends and family. "
Modern Luxury Mountain Home within Wintergreen Retreat Collection
Unwind at Bear Pause, located right at Wintergreen Resort.
Outdoor dining

Unwind at Bear Pause, located right at Wintergreen Resort.

10.0 out of 10, Exceptional, (1)
"There were a few little hiccups, the top bunk bar was not attached (not an issue as it wasn’t fully needed) and the oven was broken but I message the owner and he replied back very quickly. Neither were an issue for us. The house was perfect! Plenty of cooking supplies for our crew of 12. We loved the deck and spent plenty of time out there and there were more than enough towels for everyone. The check out rules were very clear and reasonable. I would say that something should be listed for the...
The price is CA $413
CA $883 total
includes taxes & fees
Aug 22 - Aug 23
Unwind at Bear Pause, located right at Wintergreen Resort.
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
Outdoor dining

Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

10.0 out of 10, Exceptional, (134)
"Excellent house close to the slopes"
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
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

Holiday Inn Express And Suites Waynesboro East by IHG

Holiday Inn Express And Suites Waynesboro East by IHG

10/10 Excellent
"Wonderful single night stay at this hotel, I was uncertain where to book when there is so much choice but would 100% stay here again. We had such a warm welcome from Zoe on reception who was helpful and patient with our questions. The room was perfect for us and our three children with plenty of space for bags (so much better than the Hyatt hotel we had stayed at in Washington the previous two nights at more than double the price). Breakfast was plentiful and fresh. The pool was a good temperature and clean. All the staff we met were warm and helpful, thank you and I hope we can return someday. "
Glenda 1-night trip
Posted 2 days ago
Holiday Inn Express And Suites Waynesboro East by IHG