Chalet holiday rentals in Western Maryland

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Top-rated chalet rentals in Western Maryland

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Top guest favourite
The cabin features a striking A-frame design with wooden accents and a stone chimney. Expansive glass windows enhance natural light and provide views of the surrounding forest. A spacious wrap-around porch is supported by sturdy wooden columns, inviting outdoor relaxation.
Chalet in Boonsboro
4.94 out of 5 average rating, 604 reviews

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

Top guest favourite
Chalet in Basye
4.97 out of 5 average rating, 134 reviews

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.

Top guest favourite
The exterior of a large mountain retreat is showcased against a vibrant sunset. The structure features a combination of wood and stone, with multiple windows allowing natural light. A spacious deck wraps around the front, surrounded by lush greenery and colorful trees.
Chalet in Berkeley Springs
4.97 out of 5 average rating, 101 reviews

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

Guest favourite
The exterior showcases a charming chalet surrounded by trees, featuring a spacious wrap-around deck with patio seating and a fire pit area. The large windows reflect the warm indoor lights, revealing an inviting atmosphere that complements the natural surroundings.
Chalet in Swanton
4.95 out of 5 average rating, 148 reviews

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.

Top guest favourite
An outdoor view of a two-story A-frame cabin is surrounded by vibrant trees showing autumn foliage. A spacious wooden deck extends from the cabin, featuring seating arrangements and access to the indoors. Large windows reflect natural light and provide glimpses of the surrounding nature.
Chalet in Farmington
4.98 out of 5 average rating, 192 reviews

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.

Top guest favourite
A rustic outdoor seating area features log benches arranged around a circular fire pit. The red chalet with a flag is visible in the background, surrounded by trees shedding their leaves. A gravel pathway connects the seating area and the chalet.
Chalet in Hedgesville
5 out of 5 average rating, 102 reviews

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!

Superhost
A bright and spacious living area features high ceilings with triangular windows that allow natural light to fill the space. Large glass doors open to the outdoor deck, with modern furnishings including a comfortable sofa and dining area visible in the background.
Chalet in Basye
4.85 out of 5 average rating, 257 reviews

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

Top guest favourite
An elevated view captures a spacious living area, featuring large triangular windows that invite natural light. A stone fireplace is framed by two blue sofas, accompanied by a wooden dining table with black chairs. The patio area is visible through the glass doors, extending the living space outdoors.
Chalet in Purcellville
4.98 out of 5 average rating, 116 reviews

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.

Top guest favourite
The A-frame log cabin is illuminated by string lights, showcasing its inviting façade. Large French doors open to a spacious deck, surrounded by trees, with a gravel road leading up to the property. The exterior features a blend of wood tones and a metal roof.
Chalet in Linden
4.96 out of 5 average rating, 108 reviews

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!

Guest favourite
An airy living room showcases high ceilings with exposed beams and full-length windows. A stylish sofa faces a coffee table on a patterned area rug. The space features a stone fireplace and a dining area in the background, complemented by modern kitchen amenities.
Chalet in Basye
4.93 out of 5 average rating, 183 reviews

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!

Top guest favourite
A modern two-story cabin with blue siding and a distinctive red door is nestled among trees. A gravel pathway leads to the entrance, while a small seating area is positioned on the porch. Large windows invite natural light and reveal the lush surroundings.
Chalet in Mount Jackson
4.98 out of 5 average rating, 472 reviews

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

Top guest favourite
The interior of the cabin features high ceilings with charming pine wood paneling and large windows that offer views of the surrounding nature. A cozy seating area is arranged around a wooden coffee table, with a mix of soft textures and a decorative rug anchoring the space.
Chalet in Mount Jackson
4.95 out of 5 average rating, 324 reviews

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.

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