Chalet holiday rentals in Maryland

4.94 out of 5 average rating, 572 reviews

Chalet in Boonsboro

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

4.94 out of 5 average rating, 33 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.

4.95 out of 5 average rating, 78 reviews

Chalet in Oakland

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!

Superhost

4.85 out of 5 average rating, 191 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.

4.97 out of 5 average rating, 39 reviews

Chalet in Swanton

Mountain Hideaway - Hot tub/Pond/Fire pit

Unwind with the whole family at this peaceful place to stay. The home features 3 bedrooms and 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!

4.97 out of 5 average rating, 97 reviews

Chalet in Swanton

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.

5 out of 5 average rating, 64 reviews

Chalet in Knoxville

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

4.94 out of 5 average rating, 231 reviews

Chalet in Deep Creek

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.

4.83 out of 5 average rating, 198 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.

5 out of 5 average rating, 89 reviews

Chalet in Marriottsville

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!