Chalet holiday rentals in Western Maryland

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Top-rated chalet rentals in Western Maryland

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Top Guest favourite

The exterior of a large mountain retreat is showcased against a vibrant sunset. The structure features a combination of wood and stone, with multiple windows allowing natural light. A spacious deck wraps around the front, surrounded by lush greenery and colorful trees.

Chalet in Berkeley Springs

4.97 out of 5 average rating, 100 reviews

OMG Views~Movie & Game Room~3 Levels~HotTub~Gated

Imagine waking up on top of the mountain to arguably the best view in Berkeley Springs! Enjoy the private gated luxury of Rowland Ridge! 🌞Stunning panaramic sunrises 💥Rare 3 lvl Custom-built 5,000+ sqft. ⛰MountainTop on 9 acres 🛒3.8 Miles to town 👉Screened porch & HOTTUB 🌲Huge deck, patio furniture & Gas Grill 🛌6 Bedrooms 12 beds 🛀3 FULL Baths 🎞Movie Rm with 85" TV 🏈Game Room Pool Table, wet bar, Foosball & Poker Table 🖥FAST WI-FI dedicated work space 🥩Fully stocked Chefs kitchen

Top Guest favourite

A modern multi-story home is nestled among trees, featuring large windows that enhance natural light. A spacious deck extends from the upper level. In the foreground, clusters of yellow daffodils bloom, adding a splash of color to the serene woodland setting.

Chalet in Berkeley Springs

4.96 out of 5 average rating, 189 reviews

WOW your Friends~Luxury+Fun+Secluded+Pool+Huge~

Be Still, our flagship mountain retreat!Experience an elevated escape to Berkeley Springs 8 person Hot Tub 🌳Screened in porch+2 open Decks 🥾Direct access to hiking trails PRO TIP:leads to brewery 👙Community Pool+Kiddie Pool+Jacuzzi (seasonal) 🛋️3 Family Rooms 🪵Massive Firepit+provided Firewood+Grill 🔥Cozy Propane Fireplace 🎲Pool Table+Shuffleboard table+Board Games+DVD Library 📺WIFI+two 65in TVs 🛏️5 comfy bedrooms 💆🏼‍♀️5 FULL Bathrooms+1/2 bath 🛍️5 min to downtown Berkeley Springs

Guest favourite

The exterior showcases a charming chalet surrounded by trees, featuring a spacious wrap-around deck with patio seating and a fire pit area. The large windows reflect the warm indoor lights, revealing an inviting atmosphere that complements the natural surroundings.

Chalet in Swanton

4.95 out of 5 average rating, 145 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 favourite

A spacious great room features a large sectional sofa in rich orange, inviting relaxation. Tall windows allow natural light to fill the space, offering views of the surrounding forest. A decorative area rug anchors the seating area, complemented by a coffee table and thoughtfully arranged decor.

Chalet in Hedgesville

4.94 out of 5 average rating, 177 reviews

Starcatcher Chalet, The Woods Resort

Enjoy a fun, relaxing stay at our completely renovated chalet in The Woods Resort in beautiful Berkeley County, WV--a 90-minute drive from the Washington DC-Baltimore Metro Area. You'll be in the heart of the WV Eastern panhandle, close to Sleepy Creek, Berkeley Springs, Cacapon State Park, Antietam National Battlefield, and more. The Woods Resort amenities (fees apply) include a spa, restaurant, and two golf courses, three swimming pools, tennis, pickleball, fitness, and a playground.

Top Guest favourite

A rustic outdoor seating area features log benches arranged around a circular fire pit. The red chalet with a flag is visible in the background, surrounded by trees shedding their leaves. A gravel pathway connects the seating area and the chalet.

Chalet in Hedgesville

5 out of 5 average rating, 102 reviews

Cherry Run Chalet

Kick back and relax in this peaceful, stylish chalet at The Woods community in wild and wonderful West Virginia. The 2-acre property backs up to the 23,000-acre Sleepy Creek State Wildlife Area, a hikers dream. The Woods offers 2 golf courses, indoor and outdoor pools, indoor hot tub, tennis, exercise gym and more. The Sports and Spa center is within walking distance from the chalet for self-care pampering. The Clubhouse Grille and Pub is a great option for dine in and carry out. Enjoy!

Top Guest favourite

A bright and airy living space features large triangular windows framing forest views. A stone fireplace adds warmth, while a plush sectional sofa is complemented by leather armchairs. A dining table for six is set with dishes under a stylish light fixture, enhancing the inviting atmosphere.

Chalet in Front Royal

4.95 out of 5 average rating, 150 reviews

Whitetail Summit - Shenandoah/hot tub/wineries

Whitetail Summit is a spacious chalet with stunning mountain views, river access, and hiking on property. You'll have close proximity to 30+ wineries/breweries, the Shenandoah National Park, the Appalachian Trail, the Shenandoah River, horseback riding, and hunting preserves. Or relax at home, with an indoor pool/ping pong table, music nook, outdoor hot tub, and fire pit. We are family/pet-friendly. REMOTE WORK: 600MBps wifi, two dedicated work-from-home spaces, and a GYM/PELOTON

Superhost

A bright and spacious living area features high ceilings with triangular windows that allow natural light to fill the space. Large glass doors open to the outdoor deck, with modern furnishings including a comfortable sofa and dining area visible in the background.

Chalet in Basye

4.85 out of 5 average rating, 256 reviews

Little Black Chalet - Minutes to Bryce Resort

Welcome to the Little Black Chalet located in Basye, Virginia. Minutes from the four-season Bryce Resort, Lake Laura, restaurants, orchards and wineries. Enjoy the updated contemporary and open floor plan. The house accommodates up to 6 guests, with a king bed in the loft, and two private bedrooms on the main level: with full size and 2 twin beds. The chalet includes stainless appliances, gas grill, fire pit, w/d, high-speed wifi and cable TV. Follow us on IG @littleblackchalet

Top Guest favourite

Mountains are visible in the distance, showcasing gentle slopes and a partially snow-covered landscape. Wispy clouds stretch across the sky, with soft sunlight breaking through, highlighting the tranquil beauty of the natural surroundings.

Chalet in Tucker County

4.93 out of 5 average rating, 194 reviews

The Davis Ridge - Mt Views, Fireplace, Balcony

This beautiful property is centrally located close to Davis, Thomas and Canaan Valley's most famous attractions. Witness the sunrises and sunsets over the mountains from the balcony, take a dip in the heated seasonal pool, get cozy and warm next to the wood fireplace (free firewood included), cook a delicious meal on the outdoor grill, and end the day toasting from the balcony and cuddled by the fire. You're only a few minutes from all the major sites and attractions in the area.

Top Guest favourite

An elevated view captures a spacious living area, featuring large triangular windows that invite natural light. A stone fireplace is framed by two blue sofas, accompanied by a wooden dining table with black chairs. The patio area is visible through the glass doors, extending the living space outdoors.

Chalet in Purcellville

4.98 out of 5 average rating, 116 reviews

Chalet at Harpers Ferry for Family Gatherings

Imagine waking up in your private, gated mountain vacation home nestled in nature yet minutes from history & adventuring. The upper level is your private en-suite retreat with a comfy mattress, superb linens & spa like bath. Settle in to the cozy reading alcove & enjoy the mountain vistas. On the main level is a mobility friendly queen bedroom, full bath, kitchen, dining room, & living room. Relax in the hot tub or at the fire-pit & enjoy mountain views & starry nights.

Top Guest favourite

Chalet in Linden

4.96 out of 5 average rating, 106 reviews

Liberty Chalet ~ Mt. Retreat w/4bdr SAUNA & HotTub

Welcome to Liberty Chalet, a beautiful A-frame log cabin nestled near the top of Blue Mountain, styled with a patriotic touch. Situated on 2 acres of serene, wooded land at almost 2000' elevation, this picturesque cabin provides a tranquil retreat from the hustle and bustle of everyday life. Located just a 70 minute drive from DC and only 20 minutes to Front Royal and Shenandoah National Park. Book your stay today and experience the beauty of Liberty Chalet for yourself!

Top Guest favourite

A modern two-story cabin with blue siding and a distinctive red door is nestled among trees. A gravel pathway leads to the entrance, while a small seating area is positioned on the porch. Large windows invite natural light and reveal the lush surroundings.

Chalet in Mount Jackson

4.98 out of 5 average rating, 468 reviews

Cozy Mountain Escape

Welcome! The Laurin house by @cozyescapes was started because our family wanted a place to escape to and disconnect from busy everyday life. This cozy home is nestled in woods with mountain views. We encourage you to explore the area with scenic drives or relax at a home away from home! We are excited to provide you the time and space to create an amazing escape experience. Explore & Enjoy, Rachael + Jon P.S. We are dog friendly with no additional pet fee

Top Guest favourite

The interior of the cabin features high ceilings with charming pine wood paneling and large windows that offer views of the surrounding nature. A cozy seating area is arranged around a wooden coffee table, with a mix of soft textures and a decorative rug anchoring the space.

Chalet in Mount Jackson

4.95 out of 5 average rating, 322 reviews

The Woodpecker's Chalet

The Woodpecker's Chalet is the perfect woodsy retreat with sunrise views of George Washington National Forest. The cabin is updated and fully equipped with everything you need for a cozy retreat in,, or the perfect landing spot to visit local wineries, hike, and explore the Shenandoah Valley! We are dog friendly- happy to welcome you and your dog but do require an additional fee of 50$. At this time the only pets we allow are dogs.