Chalet holiday rentals in Maryland

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Top-rated chalet rentals in 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, 588 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
The living area features a spacious sectional sofa facing a stone fireplace and a wooden accent wall. High ceilings are complemented by a spiral staircase leading to the upper level. A dining area is visible, highlighted by natural light from large windows.
Chalet in McHenry
4.96 out of 5 average rating, 45 reviews

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

Just a few steps from the lake and a private boat slip. Walk to restaurants, a local brewery, gift shops, miniature golf, go carts, an arcade and more. Less than 4 minute drive to Wisp Resort, ropes course, axe throwing, and the Garrett County Fairgrounds. Your group will be close to everything when you stay at Hartwood Haven, a centrally-located home in a lakefront community. The shared dock creates a safe area for swimming - great for the littles! This home is truly in the heart of Deep Creek.

Guest favourite
The chalet is surrounded by dense trees, showcasing its modern architecture with large windows. A spacious deck extends from the house, featuring comfortable seating options and an umbrella for shade. The natural setting offers a peaceful retreat, highlighting the home's connection to the outdoors.
Chalet in Oakland
4.95 out of 5 average rating, 81 reviews

Central Lake Area, Family Friendly - Dogs welcome!

Welcome to Parks and Deck, our centrally located, dog friendly chalet with filtered lake views just 1/4 mile from the lake! Wisp Ski Resort and Deep Creek Lake State Park are both within a 10 minute drive. After a day of adventures, relax on the deck or cuddle up in front of the fireplace with a good book and a glass of wine. Our fully-stocked kitchen is ready for you, but Brenda’s Pizza and other restaurants are just minutes away. Games, a fenced in dog run, and a pack n play are available too!

Guest favourite
The chalet features a warm wood exterior with large windows, allowing natural light to fill the interior. A spacious front deck is accessible via stairs, offering a welcoming entrance and space for outdoor seating. Lush greenery surrounds the property.
Chalet in McHenry
4.86 out of 5 average rating, 199 reviews

R & R Retreat

20% Discounts on week rentals. Lakefront 2 level chalet in McHenry, Md. on Deep Creek Lake with dock and reserved boat slip. Across the lake from WISP ski resort. Ideal and easy access and swimming in the lake. Restaurants, amusements, shops, and more only a 100 yard walk from house. 3 BR + loft, sleeps 9. Fireplace, fully furnished kitchen, TV, WIFI, A/C in summer (window units), heat and much more. Minimum 3 night stay during the summer and holidays. Beautiful view of lake and mountain.

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, 125 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
The chalet features a multi-level design with a stone and wood exterior. A spacious deck is surrounded by trimmed shrubs, offering a view of the lush green landscape. Large triangular windows provide natural light and showcase the structure's architectural detail.
Chalet in Deep Creek
4.94 out of 5 average rating, 239 reviews

A "Sweet Retreat" at Deep Creek & Wisp Ski Resort

Escape the daily grind and indulge in a rejuvenating vacation at Sweet Retreat! This charming chalet is minutes away from the vibrant attractions of Deep Creek, yet it's tucked away in a tranquil, secluded community. Just a quick drive to the picturesque shores of Deep Creek Lake and the majestic slopes of Wisp Resort. Savor the awe-inspiring sunset with the gentle glow of ski slope lights. Sweet Retreat lives up to its name, promising you a truly sweet and serene escape from the ordinary.

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, 211 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
An A-frame cabin is nestled in a wooded area, showcasing a blue exterior with large windows. A deck features two orange chairs, inviting relaxation. Surrounding trees display autumn foliage, while a layer of snow covers the ground, enhancing the tranquil setting.
Chalet in Marriottsville
5 out of 5 average rating, 95 reviews

Renovated 1973 Aframe with Hot Tub

Welcome to Hickory Roots Aframe! Nestled on a hill in the middle of a tranquil 1.13-acre lot, this luxurious 1,050 sq ft A-frame was originally built in 1973 and completely remodeled in 2023 with a mid-century design keeping in mind today's conveniences! Enjoy a relaxing stay - hang out at the fire pit, curl up with a book inside or soak in the covered hot tub. Conveniently located with easy access to I-70, I-795 and just 35 minutes from downtown Baltimore & 60 minutes from Washington DC!

Superhost
The mountain chalet is surrounded by expansive green lawns, complemented by a deck that wraps around the structure. Large windows allow for abundant natural light, and the rustic design is accented by a stone foundation and adjacent outdoor seating around a fire pit.
Chalet in McHenry
4.91 out of 5 average rating, 173 reviews

Serenity Sunsets! 2.8miles to WISP, hot-tub, pets

Welcome to "Sunset Mountain Chalet"! It’s simply awesome! Serenity defined. Absolutely beautiful mountain chalet with peaceful 360 views. You feel like you’re all alone on top of a mountain, yet you are 5 minutes to Wisp Resort and Deep Creek Lake! We challenge you to find a more peaceful sunset view than from the deck of our chalet. Enjoy the hot tub, the welcoming space inside or around the 3acres. If you have snow--invite all your friends and kids over for the sledding!

Guest favourite
The exterior of Bracken Lodge showcases a custom-built log home surrounded by lush greenery. Large windows create a connection with nature, while a stone chimney emphasizes the rustic charm. A spacious covered deck wraps around, offering outdoor seating beneath the elevated structure.
Chalet in Swanton
4.95 out of 5 average rating, 39 reviews

Deep Creek Lake One-of-a-kind 30 acre retreat!

Bracken Lodge is a custom-built log home with over 4,000 sq ft of finished living and entertaining space. The logs were dead standing timber that were repurposed as part of a salvage program from Yellowstone National Park in Montana. Every spruce log was transported east and then hand-hewn and set to create this luxurious unique vacation retreat. Named for the ferns that abound in the adjacent wildflower meadow and forest understory, Bracken lodge is truly one-of-a-kind.

Top guest favourite
The spacious mountain chalet is surrounded by lush greenery, featuring a prominent stone chimney. An expansive wooden deck extends from the upper level, complemented by a staircase leading to the grassy yard. Large windows reflect the natural light, enhancing the welcoming exterior.
Chalet in Swanton
4.98 out of 5 average rating, 46 reviews

Mountain Hideaway - Hot tub/Pond/Fire pit

Welcome to Mountain Hideaway! The home features 3 bedrooms + a sleeper sofa in the downstairs gameroom. Relax in the hot tub, fish in the pond, hike the trails, rest in the hammock, and enjoy s'mores down by the fire pit. Quiet, private, and beautiful surroundings. About 20 mins to Deep Creek State Park. Close to Savage River State Forest. About 30 mins to Wisp Resort. 8-10 guests. Perfect for a family getaway. We would love to have you stay at our cozy chalet!

Superhost
A spacious cabin features a large wrap-around deck with multiple seating areas. Expansive windows create an open feel, allowing natural light to fill the interior. A gentle slope leads to wooded surroundings, enhancing the secluded setting.
Chalet in Oakland
4.89 out of 5 average rating, 174 reviews

Private Wooded Cabin 4 Bedroom Lake Access Hot Tub

Spacious, private Deep Creek cabin. Lake access, close to Wisp, restaurants and bars. Spacious living areas on main and ground levels with room for groups. Upgraded kitchen and bathrooms. Wood burning fireplace, outdoor fire pit, and hot tub. Great for families - lots of toys and kid friendly play areas! Community lakefront area with swimming area, sandbox, and day use docks. Family managed property - we provide an individualized experience for our guests.

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