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 the house features a modern design with a peaked roof and ample windows. Warm lighting illuminates the deck and walking path, surrounded by lush greenery, creating a welcoming atmosphere. The building is nestled among trees, enhancing the feeling of a serene retreat.

Chalet in Basye

4.97 out of 5 average rating, 138 reviews

Bryce Resort | Hot Tub | Game Room | Sleeps 12

𐦂𖨆𐀪𖠋 Planning a ski trip, mountain biking weekend, or relaxing getaway with friends or family in the heart of the Shenandoah Valley?! 𐦂𖨆𐀪𖠋 The Berkshire is your answer! Thoughtfully designed for relaxed, stress-free group stays. 5 min from Bryce Resort. Close to hiking, lakes, caverns, and national park adventures. Dog-friendly and featuring a hot tub, game room, and multiple hangout spaces on 1.5-acres. Newly renovated w/ 3 levels, it is perfect for making memories together ˗ˋˏ ♡ ˎˊ˗

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, 101 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

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, 153 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.

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 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, 476 reviews

Cozy Mountain Escape

Welcome! The Laurin house by @cozyescapes was created as a place for our family to slow down, unplug, and reconnect—and we hope it feels that way for you too. Tucked in the woods with peaceful mountain views, it’s perfect for slow mornings, cozy nights, and everything in between. Explore scenic drives nearby or simply settle in and enjoy the quiet. We hope this feels like your home away from home. Explore & Enjoy, Rachael + Jon P.S. We are dog friendly with no additional pet fee

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, 257 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

Superhost

A spacious living area is showcased underneath cathedral ceilings, featuring a unique floating fireplace surrounded by a sunken conversation pit. Large windows offer views of the lush greenery outside, providing a connection to nature and an abundance of natural light.

Chalet in Basye

4.79 out of 5 average rating, 193 reviews

House over The Pond w/ Game Rooms, Views

Nestled in the Shenandoah mountains, perched over a glimmering pond, step through 2 hand-carved doors to find yourself warmly welcomed into our spacious 5 bedroom, 5 bathroom home. ✓ Conversation pit and floating fireplace with cathedral ceilings ✓ Full kitchen, stocked and ready ✓ A bathroom for each bedroom ✓ 6 comfortable beds ✓ 3 game rooms (air hockey, darts, foosball, and pool) ✓ 6 covered decks ✓ 50” TV with Roku ✓ Full-sized washer/dryer ✓ Fast Internet to work from home

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, 118 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

The A-frame log cabin is illuminated by string lights, showcasing its inviting façade. Large French doors open to a spacious deck, surrounded by trees, with a gravel road leading up to the property. The exterior features a blend of wood tones and a metal roof.

Chalet in Linden

4.96 out of 5 average rating, 113 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!

Guest favourite

The exterior of a multi-level lodge is displayed, showcasing large windows and a triangular roof. A spacious deck extends from the building, featuring a hammock and wooden railing. The surrounding green lawn adds to the serene atmosphere, complemented by a clear sky above.

Chalet in Front Royal

4.96 out of 5 average rating, 200 reviews

Bear Mountain Lodge

Bear Mountain Lodge is in the Shenandoah mountains, less than 10 minutes to the Skyline Drive - Front Royal entrance. Enjoy hiking trails, the Shenandoah River, wineries, and all of what Front Royal has to offer. Secluded property offers privacy and peace and quiet. Wifi, Cable TV, toilet paper, paper towels, shower towels, pillows, and sheets are provided. Hot Tub! Both Kuerig and drip coffee machines available. Everyday kitchen essentials included.

Top guest favourite

Chalet in Berkeley Springs

4.96 out of 5 average rating, 190 reviews

WOW your Friends+HUGE Chalet+Secluded+TOP Tier

Be Still, our flagship mountain retreat! 🌟8 person private Hot Tub 🌳Screened in porch+2 open Decks 🥾Direct access to hiking trails PRO TIP:leads to brewery 👙Community Pool+Kiddie Pool+Jacuzzi (seasonal 10 guests max per 2025) 🛋️3 Family Rooms 🪵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

Superhost

Chalet in Mount Jackson

4.91 out of 5 average rating, 293 reviews

*Hot Tub w. Mtn Views, 2 Fire pits, near Bryce!*

Cinnamon Knoll is a beautiful large A-frame perfect both a romantic getaway or a family/friends retreat. Enjoy sweeping mountain views from the home's large windows, back deck, and hot tub. The home is a great base to explore local wineries, hiking, and nearby Bryce Resort. Conveniently located 2 hrs from DC, 45 minutes from Harrisonburg, and only 20 minutes from Bayse/Bryce Ski Resort.