Chalet vacation rentals in Maryland

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Top-rated chalet rentals in Maryland

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Guest favorite

Chalet in Boonsboro

4.94 out of 5 average rating, 553 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 favorite

Chalet in Oakland

4.97 out of 5 average rating, 71 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 favorite

Chalet in McHenry

4.83 out of 5 average rating, 191 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.

Guest favorite

Chalet in Swanton

5 out of 5 average rating, 22 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!

Guest favorite

Chalet in Port Tobacco

5 out of 5 average rating, 35 reviews

River Waterfront-Dock|Canoe|HotTub|Gameroom|NearDC

Escape to the Riverpoint. This unique house embodies the charm of a Swiss chalet A-Frame, complemented by a picturesque boathouse on a serene canal of the Port Tobacco River. You’ll love the Riverpoint’s amenities: canoe launch, Italian dual oven range, hot tub, firepit, gameroom/movie room, and more! For water enthusiasts, canoe down the Port Tobacco River & watch out for Bald Eagles. Just moments from Chapel Point beach, this retreat promises relaxation & adventure for all families/groups.

Guest favorite

Chalet in Swanton

4.96 out of 5 average rating, 54 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 favorite

Chalet in Knoxville

5 out of 5 average rating, 50 reviews

4 King Suites I Hot Tub | Ping Pong, 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. Located near historic Harper's Ferry and lively Shepherdstown, you’re close to world-class hiking, biking, wineries, and more. Perfect for family or friends!

Guest favorite

Chalet in Deep Creek

4.93 out of 5 average rating, 227 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 favorite

Chalet in Marriottsville

5 out of 5 average rating, 60 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!

Guest favorite

Chalet in Oakland

4.96 out of 5 average rating, 280 reviews

Private (5 Star!) Lake Access Chalet w/ Hot Tub

Lake Forest Chalet is located on a private, dead end secluded lane with very little traffic. Bring your bikes and strollers for a stroll down the lane where kids can play and enjoy themselves without the worry of traffic rushing by. A short walk to the lake! Boat slip, Hot Tub, Firepits, and awesome outdoor area w/ Playset, Cornhole, and horseshoes. 5G internet & desk space in loft! Garage is off limits to guests, for owners use only. Disinfecting deep clean performed before every stay!

Guest favorite

Chalet in McHenry

4.91 out of 5 average rating, 161 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!

Superhost

Chalet in McHenry

4.85 out of 5 average rating, 184 reviews

R & R Retreat

25% REDUCED PRICING ON FULL 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 holiday weekends.