
Chalet holiday rentals in Western Maryland
Find and book unique chalets on Airbnb
Top-rated chalet rentals in Western Maryland
Guests agree: these chalets are highly rated for location, cleanliness and more.

Mountain Myst
A. DESCRIPTION This luxury cabin is nestled in the beautiful Blue Ridge Mountains, an hour from Washington DC. It overlooks the historic town of Boonsboro where you can watch the night lights twinkle from the top of South Mountain. Marvel at the view of Whitetail Ski Resort some forty miles away, or enjoy watching deer and turkey meander along the quiet gravel road. This home boasts log accents, vaulted ceilings and stone fireplaces in the living room and lower level. There are many upscale amenities particularly in the kitchen. The open great room and dining room open up to a modern kitchen with top-of-the-line appliances and a center island for meal prep and casual dining. From the great room step out to an expansive wrap-around porch with beautiful forest views and plenty of blue sky. Enjoy entertaining, grilling, dining outside on the deck, and campfires in the fire circle. There is a luxury master suite on the third level loft. It has a queen bed, wall mounted HDTV, sitting area, and bathroom with a walk-in, double-headed shower. The lower level has two bedrooms. One with a double bed and the other with two twin beds. There is a hall bathroom with a walk-in, double-headed shower, and separate lounging room with stone fireplace and HDTV. B. AMENITIES: • WIFI • HDTV with Full cable (4) • Kitchen stocked for cooking • Quality towels and linen(URL HIDDEN) ACTIVITIES: APPALACIAN TRAIL For a scenic stroll on the most famed of North American hiking trails, pick up the trail at the parking lot of the Washington Monument. RESTAURANTS •Old South Mountain Tavern – There has been an Inn and Tavern on this site for over 200 years •Dan’s Tap House •Vesta’s Pizza •Christies – coffee and pastry, sandwiches WINERIES There are many, but here are some of our favorites. Boonsboro MD: Big Cork Vineyards Mt. Airy MD: Linganore Winery , Black Ankle Vineyard Loudon County VA: Breaux Vineyards, Hillsborough Winery STATE PARKS Washington Monument State Park Greenbriar State Park- swimming lake Gambrill State Park Gapland State Part Cunningham Falls State Park – waterfall, swimming lake, near Camp David HARPERS FERRY WV Museums, rafting, SHEPARDSTOWN, WV Very picturesque, Great window shopping, Cafes, Potomac River FREDERICK, MD: Old Town Market Street Gettysburg Battlefield, MD (allow a full day) •Tours •Interactive museum, films •Educational Center Other Civil War battlefields Antietam, MD, Monocacy, MD, South Mountain Boonsboro SKIING Whitetail, Ski Libert(URL HIDDEN)I

Bryce Resort | Hot Tub | Game Room | Sleeps 12
★ Planning a ski trip, mountain biking weekend, or relaxing getaway with friends or family in the heart of the Shenandoah Valley? ★ Welcome to The Berkshire, a Just Happy Homes property designed for relaxed, stress-free group stays. Minutes from Bryce Resort and close to hiking, lakes, caverns, and national park adventures, this dog-friendly home features a hot tub, game room, and multiple hangout spaces on 1.5-acres. Newly renovated with three levels, it’s perfect for making memories together.

OMG Views~Movie & Game Room~3 Levels~HotTub~Gated
Imagine waking up on top of the mountain to arguably the best view in Berkeley Springs! Enjoy the private gated luxury of Rowland Ridge! 🌞Stunning panaramic sunrises 💥Rare 3 lvl Custom-built 5,000+ sqft. ⛰MountainTop on 9 acres 🛒3.8 Miles to town 👉Screened porch & HOTTUB 🌲Huge deck, patio furniture & Gas Grill 🛌6 Bedrooms 12 beds 🛀3 FULL Baths 🎞Movie Rm with 85" TV 🏈Game Room Pool Table, wet bar, Foosball & Poker Table 🖥FAST WI-FI dedicated work space 🥩Fully stocked Chefs kitchen

Ella Bella Chalet: Hot Tub, Stunning Views, Wi-Fi
Welcome to Ella Bella Chalet! Escape to our modern, yet cozy cabin boasting panoramic breathtaking views and an array of upscale amenities. Relax in the hot tub under starlit skies or gather around the fire pit for cozy evenings. Located near Wisp Ski Resort, golf courses, and endless lake activities, including boating, fishing, tubing and kayaking. Explore nearby hiking trails and attractions like Swallow Falls State Park, Adventure Sports Center International, zip lining, biking, and more.

Mountain Woods Getaway—Creek, Deck, Fireplace
Welcome to your mountain getaway— minutes away from Fallingwater, Ohiopyle State Park, and Nemacolin! Kick back and relax in this newly updated A-frame with a wood-burning fireplace, full kitchen, and spacious outdoor deck and fire-pit! You’ll be surrounded by nature with trees, ferns, and a pristine stream. Enjoy the best of both worlds with a cozy location in the woods that’s near hiking and biking trails, Youghiogheny River, Kentuck Knob, Nemacolin Casino, and Fort Necessity Battlefield.

Cherry Run Chalet
Kick back and relax in this peaceful, stylish chalet at The Woods community in wild and wonderful West Virginia. The 2-acre property backs up to the 23,000-acre Sleepy Creek State Wildlife Area, a hikers dream. The Woods offers 2 golf courses, indoor and outdoor pools, indoor hot tub, tennis, exercise gym and more. The Sports and Spa center is within walking distance from the chalet for self-care pampering. The Clubhouse Grille and Pub is a great option for dine in and carry out. Enjoy!

Little Black Chalet - Minutes to Bryce Resort
Welcome to the Little Black Chalet located in Basye, Virginia. Minutes from the four-season Bryce Resort, Lake Laura, restaurants, orchards and wineries. Enjoy the updated contemporary and open floor plan. The house accommodates up to 6 guests, with a king bed in the loft, and two private bedrooms on the main level: with full size and 2 twin beds. The chalet includes stainless appliances, gas grill, fire pit, w/d, high-speed wifi and cable TV. Follow us on IG @littleblackchalet

Chalet at Harpers Ferry for Family Gatherings
Imagine waking up in your private, gated mountain vacation home nestled in nature yet minutes from history & adventuring. The upper level is your private en-suite retreat with a comfy mattress, superb linens & spa like bath. Settle in to the cozy reading alcove & enjoy the mountain vistas. On the main level is a mobility friendly queen bedroom, full bath, kitchen, dining room, & living room. Relax in the hot tub or at the fire-pit & enjoy mountain views & starry nights.

Liberty Chalet ~ Mt. Retreat w/4bdr SAUNA & HotTub
Welcome to Liberty Chalet, a beautiful A-frame log cabin nestled near the top of Blue Mountain, styled with a patriotic touch. Situated on 2 acres of serene, wooded land at almost 2000' elevation, this picturesque cabin provides a tranquil retreat from the hustle and bustle of everyday life. Located just a 70 minute drive from DC and only 20 minutes to Front Royal and Shenandoah National Park. Book your stay today and experience the beauty of Liberty Chalet for yourself!

Hot Tub Luxe Retreat • Game Room • Lake • Bryce
Escape to Bluejay Bay—a luxury mountain chalet at Bryce Resort. Enjoy a private HOT TUB, spa-inspired bathrooms, plush bedrooms, Roku TVs, a fully equipped kitchen, cozy coffee corner, fire pit, and double decks near Lake Laura. The game room offers ping pong, foosball, Playstation, and an extensive board game library. Unwind & relax in this stylish & peaceful 2BR + loft retreat. A perfect all-season escape for couples, families, friends groups, and remote work!

Cozy Mountain Escape
Welcome! The Laurin house by @cozyescapes was started because our family wanted a place to escape to and disconnect from busy everyday life. This cozy home is nestled in woods with mountain views. We encourage you to explore the area with scenic drives or relax at a home away from home! We are excited to provide you the time and space to create an amazing escape experience. Explore & Enjoy, Rachael + Jon P.S. We are dog friendly with no additional pet fee

The Woodpecker's Chalet
The Woodpecker's Chalet is the perfect woodsy retreat with sunrise views of George Washington National Forest. The cabin is updated and fully equipped with everything you need for a cozy retreat in,, or the perfect landing spot to visit local wineries, hike, and explore the Shenandoah Valley! We are dog friendly- happy to welcome you and your dog but do require an additional fee of 50$. At this time the only pets we allow are dogs.
Popular amenities for chalet rentals in Western Maryland
Family-friendly chalet rentals

Mountain Mama Hideaway

Indian Lake, Lucky 7 Chalet

Romantic Lake Front Chalet w/Private Hot tub

Charming Mountain Chalet Tucked in the Trees

Modern Escape with Cacapon Mountain View

Modern Cabin • Hot Tub • Fire Pit • Pets • Ski

Hygge Hideaway

Mountain Hideaway - Hot tub/Pond/Fire pit
Luxury chalet rentals

Luxury Chalet: Sauna, Hot Tub, Views, Tesla EV

Sleeps 16+ • Views • Hot Tub • Theater • Game Room

Whitetail Summit - Shenandoah/hot tub/wineries

Primo Vista! Spectacular views, Dock Slip, Hot Tub

Hot Tub, 5 Resort Passes, Theater, Pet-Friendly

Hot tub * Sauna * Home theater * Game Room * Views

4 King Suites | Hot Tub | FirePit | Arcade | Games

Spectacular Chalet, Timroc II, close to lake, Wisp
Lakefront chalet rentals

Romantic Mtn Retreat | Lake + Hot Tub at Exhale

Drake's Nest on Deep Creek Lake

Deep Creek Lake - Lakefront pup-friendly Chalet!

Hartwood Haven - Steps from lake, boat slip & fun!

Lakefront A-Frame | Hot Tub, Private Dock, Views

Lakeside Retreat w/ Hot Tub & Mtn Views at Exhale

R & R Retreat

Amazing Summer Holiday and Mountain Retreat
Destinations to explore
- New York City Holiday rentals
- Western North Carolina Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Mississauga Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Pocono Mountains Holiday rentals
- South Jersey Holiday rentals
- Jersey City Holiday rentals
- Grand River Holiday rentals
- Rentals with lake access Western Maryland
- Campsite rentals Western Maryland
- Rentals with a fireplace Western Maryland
- Pet-friendly rentals Western Maryland
- Flat rentals Western Maryland
- Bed and breakfasts Western Maryland
- Rentals with a patio Western Maryland
- Motorhome rentals Western Maryland
- House rentals Western Maryland
- Rentals with breakfast Western Maryland
- Fitness-friendly rentals Western Maryland
- Hotel rooms Western Maryland
- Farm stay rentals Western Maryland
- Waterfront rentals Western Maryland
- Rentals with a kayak Western Maryland
- Rentals with a cinema Western Maryland
- Family-friendly rentals Western Maryland
- Cabin rentals Western Maryland
- Cottage rentals Western Maryland
- Rentals with outdoor seating Western Maryland
- Rentals with a hot tub Western Maryland
- Smoking-friendly rentals Western Maryland
- Apartment rentals Western Maryland
- Boutique hotels Western Maryland
- Tiny house rentals Western Maryland
- Private suite rentals Western Maryland
- Ski-in/ski-out rentals Western Maryland
- Rentals with a firepit Western Maryland
- Townhouse rentals Western Maryland
- Rentals with a sauna Western Maryland
- Rentals with a washing machine and dryer Western Maryland
- Guest house rentals Western Maryland
- Rentals with pools Western Maryland
- Rentals with an EV charger Western Maryland
- Chalet rentals Maryland
- Chalet rentals United States
- Seven Springs Mountain Resort
- Timberline Mountain
- Wisp Resort
- Fallingwater
- Idlewild & SoakZone
- White Grass
- Ohiopyle State Park
- Canaan Valley Resort & Conference Center
- Canaan Valley Ski Resort
- Green Ridge State Forest
- West Virginia University
- Rock Gap State Park
- Deep Creek Lake State Park
- Tygart Lake
- Swallow Falls State Park
- Laurel Hill State Park
- Coopers Rock State Forest
- Fort Necessity National Battlefield
- Fort Ligonier
- Laurel Ridge State Park




