Chalet holiday rentals in Western Maryland

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Top-rated chalet rentals in Western Maryland

Guests agree: these chalets are highly rated for location, cleanliness and more.

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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, 146 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, 191 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.

Guest favourite

A welcoming cedar chalet sits on a gently sloping lawn, featuring a raised deck with lattice detailing. Large windows align the facade, allowing natural light to fill the space. The surrounding greenery enhances the serene setting, and a side glimpse of a pedal boat is visible.

Chalet in McHenry

4.83 out of 5 average rating, 215 reviews

Drake's Nest on Deep Creek Lake

This waterfront/slopeview chalet offers beautiful views of the lake and ski slopes. Convenience stores, amusements and restaurants located a short walk away. Rental includes use of a pedal boat, swim inflatables, tow tubes and boat slip. The deck offers seating for 10; grills and picnic available. Visitors during Spring & Autumn enjoy Swallow Falls/Muddy Creek Falls ( tallest in MD) 15 min drive. *Holiday weekends require a 3 night minimum. *Renters under 25 may be charged a damage deposit.

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!

Guest favourite

Two wooden Adirondack chairs are positioned on a spacious deck, facing panoramic views of the blue sky and distant mountains. Lush trees and greenery fill the scene, creating a serene outdoor atmosphere.

Chalet in Rileyville

4.94 out of 5 average rating, 174 reviews

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub

The Chalet is a 2 bedroom, 2 bath cabin with a spectacular view of the Blue Ridge Mountains. Amenities include: *4 person Hot Tub *43" Smart TV with Chromecast *Wifi *1 Full & 1 Half Bathroom * Electric Fireplace in LR *Fully equipped kitchen *Pet Friendly ($25 per night) *1/2 mile walk to the Shenandoah River We are located just 7 miles north of Luray, VA. and 20 minutes from Shenandoah National Park. The Chalet is the perfect place to relax and enjoy time in the Shenandoah Valley.

Top guest favourite

An aerial view of a spacious log home set amidst verdant landscaping. The fenced-in yard features a sparkling pool surrounded by lounge chairs and an umbrella for shade. The expansive deck is visible, leading to the home, with lush trees framing the serene outdoor space.

Chalet in Purcellville

4.96 out of 5 average rating, 111 reviews

6BR Villa Vinewood Estate & Adventures

Conquer Virginia Wine Country at Vinewood Estate. Experience a 5,500 sq. ft. Montana-style log home nestled on a 10-acre active vineyard. We offer a high-touch, "Ease of Everything" model designed for luxury retreats, weddings, and groups. From our private Estate-Crafted Wine to our bespoke Airstream Vineyard and River Expeditions, we handle the logistics so you can focus on the memories. This is a secluded sanctuary where rugged log-home charm meets Restoration Hardware refinement.

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, 107 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

The exterior of a charming chalet features deep brown wood siding, red shutters, and colorful window boxes filled with flowers. A clock adorns the front, while a welcoming porch with railings provides access to the entrance. Lush greenery surrounds the structure.

Chalet in Harpers Ferry

4.93 out of 5 average rating, 149 reviews

The Cuckoo Chalet

We invite you to come stay "just up the mountain" from historic Harpers Ferry National Park. The Cuckoo Chalet is our happy place and a labor of love. Enjoy 3 bedrooms with queen beds (plus one twin bed and additional twin mattresses without frames upon request) and 2 bathrooms. Make yourself at home in our indoor and outdoor gathering spaces. Grill out, enjoy the fire pit, tube the river, watch for deer, hike trails, play pool or read a good book in the hammock.

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, 182 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, 470 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

Guest favourite

Chalet in Mount Jackson

4.92 out of 5 average rating, 286 reviews

*Hot Tub w. Mtn Views, 2 Fire pits, near Bryce!*

Cinnamon Knoll is a beautiful large A-frame perfect both a romantic getaway or a family/friends retreat. Enjoy sweeping mountain views from the home's large windows, back deck, and hot tub. The home is a great base to explore local wineries, hiking, and nearby Bryce Resort. Conveniently located 2 hrs from DC, 45 minutes from Harrisonburg, and only 20 minutes from Bayse/Bryce Ski Resort.