Chalet holiday rentals in Maryland

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Top-rated chalet rentals in Maryland

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Guest favourite

Chalet in Boonsboro

4.94 out of 5 average rating, 523 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

5 – 12 Feb

$3,916 AUD total

Guest favourite

Chalet in Oakland

4.97 out of 5 average rating, 61 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!

9 – 16 Jan

$3,522 AUD total

Guest favourite

Chalet in McHenry

4.81 out of 5 average rating, 170 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.

14 – 21 Apr

$2,060 AUD total

Guest favourite

Chalet in Deep Creek

4.93 out of 5 average rating, 211 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.

14 – 21 Dec

$4,582 AUD total

Guest favourite

Chalet in Oakland

4.96 out of 5 average rating, 248 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!

10 – 17 Oct

$4,925 AUD total

Guest favourite

Chalet in Marriottsville

5.0 out of 5 average rating, 30 reviews

Renovated 1973 Aframe

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!

11 – 18 Sept

$3,724 AUD total

Guest favourite

Chalet in McHenry

4.92 out of 5 average rating, 145 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!

21 – 28 Aug

$6,247 AUD total

Guest favourite

Chalet in Oakland

4.86 out of 5 average rating, 128 reviews

Big Rock Candy Mountain Lodge - Deep Creek Lake

*Kitchen and 2 bathrooms renovated 5/2023. Comfortably nestled in a hillside only one street from the lake, Big Rock Candy Mountain Lodge is a 5 bedroom, 4 full bath lodge where modern meets traditional. Centrally located yet secluded, it is less than 4 miles from skiing, ziplining & the coaster @ Wisp, the ASCI adventure park, plus the movie theater, restaurants and hiking! The area truly offers four seasons of fun with skiing, golf, swimming, hiking, kayaking, and fishing.

11 – 18 Nov

$4,339 AUD total

Superhost

Chalet in Swanton

4.81 out of 5 average rating, 86 reviews

Deep Creek Lake Retreat

Come relax at our 4 level, 5 bedroom, 5 full bath lake mountain chalet that is tucked into the hillside, just one road away from the lake. The space allows for everyone to congregate on the main level or to spread out throughout the 4 levels. Play on our community tennis court and enjoy Deep Creek Lake through the lake access area. Take a short trip to Deep Creek State Park and enjoy the beach, hiking trails, and many more things to do. Travel 4 miles to the Wisp Ski Resort.

6 – 13 Oct

$8,531 AUD total

Guest favourite

Chalet in Swanton

5.0 out of 5 average rating, 22 reviews

Deep Creek Lake One-of-a-kind Retreat on 22 acres!

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.

23 Feb – 2 Mar

$11,034 AUD total

Guest favourite

Chalet in Oakland

4.9 out of 5 average rating, 125 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.

19 – 26 Sept

$4,270 AUD total

Guest favourite

Chalet in Oakland

5.0 out of 5 average rating, 88 reviews

Family friendly w/ Hot tub, Deck, Firepit

The Dacha is in a forested space on a hill with filtered views of the lake, close to all local attractions, but away from the drone of motorboats and lake noise. The cozy cabin offers a hot tub, deck, gas fireplace, fire pit, well equipped kitchen, an arcade, games, and local wildlife! We have young children so the home is furnished to be family friendly and with conveniences we use in our daily lives. We welcome you to enjoy it with us.

16 – 23 Sept

$3,491 AUD total