
Chalet holiday rentals in Shenandoah
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Top-rated chalet rentals in Shenandoah
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Family-friendly chalet rentals

The Cuckoo Chalet
This is my family's third time staying at the Cuckoo Chalet. We really enjoy the location and the amenities -- It has everything we need for a long weekend away from home.

Massanutten For Kids w/ playroom and family fun!
The cabin was perfect for staying with our two kids. The playrooms and well stocked kitchen and rooms made it easy to keep them entertained and relax in the mountains. Thank you for your hospitality!

"The Duke Den"
Only suggestions they need another frying Pan and Maybe a few other pans for Kitchen. Place was Super nice! Definitely would recommend

Private Lake Anna Waterfront Chalet w/dock/beach!
Perfect little getaway. Christine is incredibly responsive. We’ll definitely be back.

Mountainside getaway in the heart of resort
Mary and Chris’s property felt like home for us!! We loved the cabin feel, the spacious layout and the well stocked kitchen. We had more than what we needed, as far as dishes to create some magical meals. Thank you for hosting our family and we will be sure to return the next time we are looking some relaxation!

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub
Location!! Near all local attractions but extremely private. Beautiful views. Loved waking up to beautiful sunrises from the comfort of bed, and amazing stars at night from the hot tub on the back deck. This house delivers a great experience. Would absolutely stay again

River’s Edge Retreat on the Deep Water Potomac
We had a wonderful stay at Amy’s place. The location is beautiful (especially when it snows!) and the house was spacious and well taken care of/furnished. Also lots of board games etc available. Amy was also really helpful and proactive, offering to let us leave later on check out day due to a snow storm. Would definitely recommend to anyone looking for a peaceful escape near Harpers Ferry!

Big, Bright SLOPESIDE Ski Chalet, Outdoor Hot Tub!
This place was AWESOME! Perfect location for wanting to spend your time on the slopes! Super cozy, very spacious, looks exactly like the pictures. The living area is a great hangout spot and the fireplaces kept us nice and warm during this windy winter stay.
Luxury chalet rentals

Sleeps 16+ • Views • Hot Tub • Theater • Game Room
Beautiful property! The decor was top notch and the kitchen was fully stocked. We had a small concern and Lea handled it very professionally. Overall Lea was very kind and quick to respond. Highly recommend!

Sky Island Chalet
The view is beautiful! The main space is perfect for relaxing and visiting - but the bedrooms have enough space between them to provide some quiet and privacy for groups that have both early birds and night owls. Listening to the birds while sitting in the hot tub was especially relaxing, after attending a busy family gathering at a nearby winery.

Whitetail Summit - Shenandoah/hot tub/wineries
We were a combined bunch of 8 adults and a 3 yr old. We had an incredible time, despite having a week of mostly rainy weather. There is plenty to do in the house and it is very comfortable. The kitchen is well stocked with small appliances and utensils. The house is kid-friendly and has all you need to entertain the kids and accommodate toddlers. The location is quiet and secluded, but close enough to a variety of attractions to keep you busy in good weather. We had a precious time and were sad to leave. Jenny was very communicative and responsive. She provided us with all the details we needed to enjoy the stay.

Luxury 7BR/16 pp Wintergreen ski & ping pong/darts
Kathryn’s place was AMAZING! We came here for a bachelorette celebration and it was such a nice, peaceful getaway! All the beds were comfortable and had plenty of space to decorate how we wanted for the bach trip! We couldn’t be more pleased with the place!

6BR Modern Massanutten Chalet with Hot Tub, Sauna
Our stay at this Airbnb was incredible!!! The rooms and living spaces were comfortable and clean, and there was a ton of provided items such as towels for the hot tubs, blankets, games, and tons of kitchenware. The host was very responsive to questions and proactively provided information for check-in and check-out! The location was quiet and beautiful, and was the perfect cabin get away for our big group. Would definitely love to come back!

Mountain Views, Hiking, Ski-Out @ Tyro
Book this gem! You will NOT be disappointed! Squeaky clean with high quality amenities! I have zero criticism and only positive comments. Linens, furniture, decor, deck, kitchen, updated, tasteful bathrooms and views for miles! Be sure to rise early to catch that eastern sunrise that seems to be painted in the sky over the mountains. Mark my words, this home will be a top contender for best airbnb to stay in at Wintergreen!

4 King Suites | Hot Tub | FirePit | Arcade | Games
We could not have been more thrilled with our stay at this AIRBNB. The home is as depicted in the pictures, very spacious, beautifully decorated…and so many spaces to enjoy! I wanted to pull out the kitchen and take it home with me - dreamy! We enjoyed the deck as well for a large family meal. We commuted to Baltimore for my daughter’s graduation which was not a problem. If you are a wine lover, do not miss out on Big Cork Vineyards, what a treat! Blair and Nadia are fantastic, very responsive and communicative!

River Retreat-luxury near Skyline Drive-EV charger
We spent a couple relaxing nights at this beautiful home in the mountains and it couldn’t have been better. Beautiful, spacious and modern feel with huge windows and views. The kitchen was outfitted with everything we needed to prep meals, and we also loved the coffee/bar sitting room right by the front door. Accessible to town but also feels like a remote and peaceful hideaway. Our hosts were super proactive, responsive and flexible as we juggled multiple people and arrival/departure times—so appreciated. This place is a true gem and we will be back!! ❤️
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- Massanutten Resort
- Luray Caverns
- Ash Lawn-Highland
- Early Mountain Winery
- Bryce Resort
- Chisholm Vineyards at Adventure Farm
- Prince Michel Winery
- Shenandoah Valley Golf Club
- Spring Creek Golf Club
- Massanutten Ski Resort
- Sly Fox Golf Club
- Bowling Green Country Club
- Wintergreen Resort
- The Plunge Snow Tubing Park
- Frontier Culture Museum
- Car and Carriage Caravan Museum
- Warden Lake
- Dinosaur Land