Search Chalets in Sherando from CA $547

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Browse Select Sherando Chalets

Situated in a forested area, this cabin features a gable roof and a front porch with a bench.

"I loved this place! There was plenty of space for family and the cabin was beautiful! We enjoyed the porch and firepit and the fireplace inside. The cabin was easy to find. I would stay here again."

Enjoy dining or socializing on the deck with a table and chairs.

"We had a pleasant stay at the property. It was quiet and peaceful, exactly what we needed since we had a busy event scheduled."

Relax on the deck with a telescope, taking in the breathtaking mountain views.

"The location and view (and privacy) were outstanding. The house is cute, easily accommodates 2 people (4 would be ok, but bathroom sharing amongst 4 could be a challenge), and has all of the amenneties to ensure maximimum comfort (blue tooth speaker, decently stocked kitchen, coffee and related items, cute decor, and plenty of towels and hot water."

Relax in a hot tub with mountain views, surrounded by a wooden deck and large windows.

"Great house, great owner, incredible views. As good as it gets in the entire mid-Atlantic"

CA $2,371 total

includes taxes & fees

Aug 3 - Aug 4

"Great location for a quick weekend getaway. Amenities were a plus and great access to Wintergreen resort. "

Relax in a hot tub under a shaded pergola with breathtaking views of the night sky and surrounding landscape.

"This place absolutely lives up to its descriptions. Unbeatable views. Also the game room is amazing. "

CA $1,022 total

includes taxes & fees

Aug 19 - Aug 20

Enjoy a serene forest view from the comfort of your room, with a deck and expansive windows.

"We had a fantastic stay! Location is great, very clean and comfortable. Would not hesitate to return! "

Enjoy a meal under the stars at this charming outdoor seating area with tables, chairs, and umbrellas.

"This house was very spacious and well stocked. It was close to all of our activities. "

Enjoy dining al fresco on the spacious deck with comfortable seating and a glass door leading to the indoor space.

"My family and I recently spent a long weekend in August at this family-friendly chalet in Wintergreen and loved every moment. The owners really thought of everything! Highly recommend! "

Stunning two-story house with a charming front porch and gabled roof, surrounded by lush greenery.

"Just like the pictures, don't hesitate! Just book!!"

Step into this charming cabin, featuring a cozy front porch with a staircase leading to an upper deck and a tranquil wooded setting.

"This house was perfect for our family of 13, Ages 86 to 3. The men played golf followed by a game of pool and relaxed in the hot tub We all loved the deck and how peaceful the neighborhood is. The house is very clean and comfortable."

Guests can enjoy a serene forest view from this elevated deck.

"The location was great for a ski vacation - an easy walk to the main lodge even with kids.The property itself is dated and could use a number of upgrades. Very basic amenities and light blankets on the beds - would definitely recommend bringing extra blankets (and towels) if you plan to stay for a cold weekend. The listing noted that there is access to an indoor pool which we found out was not the case and the property does not have resort access. "

Escape to a serene forest retreat with a cozy cabin-style lodging featuring a welcoming front porch and lush surroundings.

"The communication was excellent before and during the stay - they checked in and followed up with us. The property had everything we needed for a great weekend. A quick 2 minute drive to the Wintergreen restaurants and small store. "

Save an average of 15% on thousands of hotels when you're signed in

Top Sherando Hotel Reviews

Comfort Inn

10/10 Excellent

"Staff was great. Place is old but clean, no bugs, bed was comfy breakfast was nice. Those are the things that matter to me😊plus I’m a little handicap so bottom floor was convienient."