Chalet holiday rentals in Maryland

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Top-rated chalet rentals in Maryland

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Top Guest favourite

Chalet in Boonsboro

4.94 out of 5 average rating, 568 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

Guest favourite

Chalet in Oakland

4.95 out of 5 average rating, 76 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

Chalet in McHenry

4.83 out of 5 average rating, 193 reviews

Drake's Nest on Deep Creek Lake

This cedar chalet offers the best of both worlds. It is located on the water's edge (really) and offers spectacular views of the slopes at Wisp ®. Convenience stores, amusements and restaurants located a short walk away. Rental includes use of a pedal boat, swim inflatables, tow tubes and boat slip. Visitors during Spring and 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

Chalet in Swanton

5 out of 5 average rating, 33 reviews

Great Location - Balcony View - Hot Tub - Fire Pit

Location! Location! Location! Welcome to Claire’s Cove, a charming Chalet at Deep Creek Lake! Your 5-Bedroom 4-Bath cabin has an enormous wrap around deck, vaulted ceilings, two stacked stone fireplaces, lower level game room, and tons of glass to bring in filtered views of Deep Creek Lake! Minutes from Lake Access, state parks and beaches, local restaurants, and Wisp Ski Resort. Enjoy the cool evenings around your outdoor firepit or soak up the mountain air from your private covered hot tub!

Superhost

Chalet in McHenry

4.85 out of 5 average rating, 189 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

Chalet in Swanton

4.98 out of 5 average rating, 90 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.

Superhost

Chalet in McHenry

4.93 out of 5 average rating, 103 reviews

Primo Vista! Spectacular views, Dock Slip, Hot Tub

Welcome to ‘Point of View’! Come relax at this beautiful 5-bedroom home with unmatched views of Deep Creek Lake! Enjoy panoramic views of the lake from the deck, great room, dining room, master bedroom, lower level game room and outdoor stone patio. Bring your boat to create those fun lake memories, as a private dock slip is just down the hill on a protected part of DCL. Wind down your day under the stars on the newly constructed outdoor stone patio that includes a new hot tub and fire pit.

Top Guest favourite

Chalet in Knoxville

5 out of 5 average rating, 59 reviews

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

Welcome to Haven Away, where you can escape to your own mountain paradise! This brand-new hideaway offers 4 luxurious king ensuite bedrooms, a spacious kitchen and dining area, a relaxing hot tub, a game room with an arcade machine, ping pong, and yoga space. Enjoy board games and outdoor activities on your private 3-acre wooded estate. - 17 min drive to historic Harpers Ferry - 20 min drive to Shepherdstown - 30 min drive to hip and happening Frederick, VA - 14 mins from Big Cork Vineyard

Top Guest favourite

Chalet in Deep Creek

4.93 out of 5 average rating, 230 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.

Superhost

Chalet in Oakland

4.91 out of 5 average rating, 128 reviews

Spectacular Chalet, Timroc II, close to lake, Wisp

ENJOY every season!! Short walk to the lake and dock! ! 15 minute drive to Ski Wisp! Fire pit, decks and screened in porch! Relax in the hot tub, enjoy family and/ or friends time and just get away from it all! 5 comfortable sized bdrms, each with large windows letting in natural daylight. First floor master, hardwood flooring throughout, many sliders for easy access. Finished bsmt with pool table, separate bdrm, full bath and laundry! DON'T SEE YOUR DATE, PLEASE CALL!

Superhost

Chalet in Swanton

4.94 out of 5 average rating, 31 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.

Guest favourite

Chalet in Oakland

4.9 out of 5 average rating, 158 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.