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, 592 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
An open living area showcases a cozy seating arrangement with leather couches and a central coffee table, complemented by a stone fireplace. A wooden staircase leads to a lofted space, while ceiling fans circulate air throughout the room, which is adorned with neutral tones and wooden accents.
Chalet in Somerset
4.94 out of 5 average rating, 175 reviews

Charming Mountain Chalet Tucked in the Trees

Welcome to The Burrow! This 4 bedroom, 3 bath chalet is located on almost 2 acres right off the main road within minutes of the Hidden Valley Resort entrance. A picturesque chalet, hidden amongst the trees and ready for you to leave your worries at the door and relax. With plenty of space for 8 people to find 'their spot', whether next to the fireplace looking out the sliding glass doors at mountains, by the smart tv with your favorite show, or cooking your go-to meal in the spacious kitchen!

Top guest favourite
The exterior of the chalet is shown surrounded by a snowy landscape, with the deep blue structure contrasting against the white snow. Large windows allow for natural light to fill the interior, while a spacious deck is visible on the left.
Chalet in Berkeley Springs
4.96 out of 5 average rating, 185 reviews

~Close to Downtown~Campfire Nites~Large Gathering

Be Still, our flagship mountain retreat!Experience an elevated escape to Berkeley Springs 8 person Hot Tub 🌳Screened in porch+2 open Decks 🥾Direct access to hiking trails PRO TIP:leads to brewery 👙Community Pool+Kiddie Pool+Jacuzzi (seasonal) 🛋️3 Family Rooms 🪵Massive Firepit+provided Firewood+Grill 🔥Cozy Propane Fireplace 🎲Pool Table+Shuffleboard table+Board Games+DVD Library 📺WIFI+two 65in TVs 🛏️5 comfy bedrooms 💆🏼‍♀️5 FULL Bathrooms+1/2 bath 🛍️5 min to downtown Berkeley Springs

Top 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
4.98 out of 5 average rating, 129 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.

Guest favourite
A spacious great room features a large sectional sofa in rich orange, inviting relaxation. Tall windows allow natural light to fill the space, offering views of the surrounding forest. A decorative area rug anchors the seating area, complemented by a coffee table and thoughtfully arranged decor.
Chalet in Hedgesville
4.94 out of 5 average rating, 170 reviews

Starcatcher Chalet, The Woods Resort

Enjoy a fun, relaxing stay at our completely renovated chalet in The Woods Resort in beautiful Berkeley County, WV--a 90-minute drive from the Washington DC-Baltimore Metro Area. You'll be in the heart of the WV Eastern panhandle, close to Sleepy Creek, Berkeley Springs, Cacapon State Park, Antietam National Battlefield, and more. The Woods Resort amenities (fees apply) include a spa, restaurant, and two golf courses, three swimming pools, tennis, pickleball, fitness, and a playground.

Top guest favourite
A modern living area is featured, highlighted by a spacious white sectional sofa with decorative pillows. A large flat-screen TV is mounted on the wall opposite, while expansive windows offer views of the surrounding trees and outdoor seating on the deck.
Chalet in Front Royal
4.94 out of 5 average rating, 108 reviews

River Retreat-luxury near Skyline Drive-EV charger

Relax in this luxe modern cabin near Shenandoah National Park! Modern, stylish, comfortable with amazing views of the river and mountains. Grab a meal from nearby charming Front Royal or cook a meal in our chef's kitchen. A newly built vacation house: perfect for a getaway with friends or family. All the modern comforts in the countryside, and a hot tub! Skyline Drive: 5 minutes. Luray Caverns-20 minutes south. Inn at Little Washington: 30 minutes. Visit wineries in all directions.

Top guest favourite
Mountains are visible in the distance, showcasing gentle slopes and a partially snow-covered landscape. Wispy clouds stretch across the sky, with soft sunlight breaking through, highlighting the tranquil beauty of the natural surroundings.
Chalet in Tucker County
4.93 out of 5 average rating, 178 reviews

The Davis Ridge - Mt Views, Fireplace, Balcony

This beautiful property is centrally located close to Davis, Thomas and Canaan Valley's most famous attractions. Witness the sunrises and sunsets over the mountains from the balcony, take a dip in the heated seasonal pool, get cozy and warm next to the wood fireplace (free firewood included), cook a delicious meal on the outdoor grill, and end the day toasting from the balcony and cuddled by the fire. You're only a few minutes from all the major sites and attractions in the area.

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, 110 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.

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, 177 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!

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, 247 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, w/ 1 king sized bed in the loft, and two private bedrooms: w/ full size and 2 twin. The chalet includes stainless appliances, grill, fire pit, w/d, high-speed wifi and cable TV. Follow us on IG @littleblackchalet

Top guest favourite
A fire pit is illuminated in warm tones, with 'Lakefront Libations' cut into its metal design. Surrounding stones create a rustic border, while the serene lake glimmers softly in the background under a twilight sky. Gentle waves can be seen lapping at the shore.
Chalet in Central City
4.96 out of 5 average rating, 115 reviews

Romantic Lake Front Chalet w/Private Hot tub

A unique and secluded lakefront chalet tucked away in a canopy of beautiful oak trees. Lakefront Libations is located on Indian Lake and boasts modern amenities in the heart of nature. You can relax in the hot tub, kayak on the pristine lake or enjoy your favorite drink by the firepit. This chalet is close to ski resorts, marina, ATV parks, golf courses and the Flight 93 Memorial. Your intimate escape to the Laural Highlands awaits you!

Guest favourite
The exterior of the house features a modern design with a peaked roof and ample windows. Warm lighting illuminates the deck and walking path, surrounded by lush greenery, creating a welcoming atmosphere. The building is nestled among trees, enhancing the feeling of a serene retreat.
Chalet in Basye
4.97 out of 5 average rating, 120 reviews

*NEW* HotTub | GameRoom | Large Deck | DogFriendly

Welcome to The Berkshire on Bryce Mountain - a Just Happy Homes property! Nestled on 1.5 acres, this luxury 4 bed, 3 bath, newly renovated home is just minutes from Bryce Resort. Complete with a hot tub, games, beautiful kitchen, and multiple indoor and outdoor hang-out spaces, this home is the perfect gateway for friends and family (and dogs) seeking outdoor adventures or simply a relaxing getaway in the breathtaking Shenandoah Valley.

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