Chalet holiday rentals in Maryland

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!

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 chef's kitchen, a relaxing hot tub, a game room with an arcade machine, ping pong, a yoga space AND hi speed internet. 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 - 50 mins to Whitetail Ski Resort

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.

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.

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.

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!

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.

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!

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!