
Chalet holiday rentals in Shenandoah
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Top-rated chalet rentals in Shenandoah
Guests agree: these chalets are highly rated for location, cleanliness and more.
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Popular amenities for chalet rentals in Shenandoah
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!
We come down twice a year for boating events and her place was in a great location for a little of everything. Boating, Fishing etc

"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

3 Masters Perfect for Multiple Families&NewArcade!
Highly recommend this home for your Wintergreen stay. First, the hosts were extremely proactive in sending detailed information from check-in instructions to suggestions on local activities. The host was responsive within minutes with any questions we had. The house is very well stocked with everything you will need for your stay. The house was very clean, spacious, and comfortable. It was perfect for 3 couples in our party, not many homes have 3 master suites. The house has 2 family rooms which added great additional space. The location is convenient to the Wintergreen lodge, not ski in/ski out but an easy drive down to the resort, seriously just a few minutes. I highly recommend waking up early to enjoy the beautiful sunrise from the big window on the main level, can't beat the views. Everyone in our party was extremely happy with our stay.

Tree top home in Massanutten next to tubing
Beautiful home, spacious, it was a great peaceful getaway

Wintergreen Retreat
Nathan and the house are truly remarkable, showcasing qualities like amazing, incredible, outstanding, beautiful, kind, generous,sincere and phenominal. I highly recommend them! All praises and blessings! When you book with Nathan, all you need is money and food because they provide everything else you could possibly want and more. Plus, the price is absolutely fair! 🙂
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.

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!

Modern 5BR Getaway! Hot tub, Arcade, Spa & Chef
Great accommodations for group trips. There are a number of in home activities; games, karaoke, hot tub, etc readily available. Proximity to Massanutten slopes was the selling point for our group of beginner skiers NOT interested in ski in/ski out options.

Opulent Retreat- Hot Tub* Fire Pit*Wheelchair Ramp
The house was the perfect location to celebrate our son’s engagement with his fiancé and her family!

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!

25% off~Theater~Hot Tub~Slopes
We had a great time at Bridget and Preston’s chalet as family with little ones. The movie theater was a great touch and kids loved winding down with a movie. Lots to do in the surrounding areas as well. Hosts were very responsive and communicated clearly. Will definitely recommend.
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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
- Sly Fox Golf Club
- Spring Creek Golf Club
- Bowling Green Country Club
- Massanutten Ski Resort
- Wintergreen Resort
- The Plunge Snow Tubing Park
- Frontier Culture Museum
- Car and Carriage Caravan Museum
- Warden Lake
- Dinosaur Land