Chalet holiday rentals in Western Maryland

Find and book unique chalets on Airbnb

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Popular amenities for Western Maryland chalet rentals

Family-friendly chalet rentals

Guest favourite
Chalet in Harpers Ferry
4.93 out of 5 average rating, 141 reviews

The Cuckoo Chalet

RyanRating, 5 stars1 month ago
This is my family's third time staying at the Cuckoo Chalet. We really enjoy the location and the amenities -- It has everything we need for a long weekend away from home.
Guest favourite
Chalet in Basye
4.79 out of 5 average rating, 182 reviews

"The Duke Den"

StevenRating, 5 stars2 weeks ago
Only suggestions they need another frying Pan and Maybe a few other pans for Kitchen. Place was Super nice! Definitely would recommend
Guest favourite
Chalet in Confluence
4.93 out of 5 average rating, 221 reviews

Paddler's Lane Retreat - Riverside Chalet

BruceRating, 5 stars1 week ago
Chalet was a great getaway spot for a few days for an annual fishing trip. Every detail was perfect for us, had everything you could think of and thoroughly thought through the details to make sure you had all amenities needed. Grounds were also beautiful. People mention trains in their reviews but honestly didn’t mind it one bit, if you wanted they even had ear plugs in each room. Thanks again and our guide this week said he has had others stay there as well Bruce
Guest favourite
Chalet in Rileyville
4.94 out of 5 average rating, 167 reviews

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub

StevenRating, 5 stars2 months ago
Location!! Near all local attractions but extremely private. Beautiful views. Loved waking up to beautiful sunrises from the comfort of bed, and amazing stars at night from the hot tub on the back deck. This house delivers a great experience. Would absolutely stay again
Top Guest favourite
Chalet in New Paris
4.9 out of 5 average rating, 189 reviews

Hemlock Hills Farm

IlisaRating, 5 stars2 weeks ago
This property is spectacular! Fabulous hiking, huge pond, a basement filled with fun (pool, ping pong, air hockey, and SO many games). Even with less than stellar weather, we were able to fully enjoy the house and property. There are plenty of covered spaces to enjoy the stellar views and stay dry. The fireplace and wood (thank you!!) meant that we were warm and cozy for our stay. Thank you for sharing this lovely property!!
Superhost
Chalet in Chalkhill
4.65 out of 5 average rating, 83 reviews

Vineyard View Chalet w/ Hot Tub!

DouglasRating, 5 stars6 months ago
Thanks David. If you ever are in need of a friend's getaway this is the place to go.
Superhost
Chalet in Shepherdstown
4.89 out of 5 average rating, 244 reviews

River’s Edge Retreat on the Deep Water Potomac

MicahRating, 5 stars4 months ago
We had a wonderful stay at Amy’s place. The location is beautiful (especially when it snows!) and the house was spacious and well taken care of/furnished. Also lots of board games etc available. Amy was also really helpful and proactive, offering to let us leave later on check out day due to a snow storm. Would definitely recommend to anyone looking for a peaceful escape near Harpers Ferry!
Superhost
Chalet in Champion
4.87 out of 5 average rating, 61 reviews

Bear Claw Chalet at Claycomb Chalets

JakeRating, 5 stars1 month ago
The cabin may look small in pictures but their use of space and design works perfect. It all felt very comfortable and cozy. The place was in immaculate condition. We had the cabin far right tucked away. Didn’t get a chance to use the fire pit but everything was there if needed. If you’re looking for what feels like a hunting lodge getaway this is the place. The owners really worked with us on multiple things and were very responsive. I would and have thought about staying again and recommended it to a few others. You’ll love it there and the owners. No complaints.

Luxury chalet rentals

Guest favourite
Chalet in Basye
4.96 out of 5 average rating, 97 reviews

Sleeps 16+ • Views • Hot Tub • Theater • Game Room

SabeenRating, 5 stars1 month ago
Beautiful property! The decor was top notch and the kitchen was fully stocked. We had a small concern and Lea handled it very professionally. Overall Lea was very kind and quick to respond. Highly recommend!
Guest favourite
Chalet in McHenry
4.91 out of 5 average rating, 167 reviews

Serenity Sunsets! 2.8miles to WISP, hot-tub, pets

MarinaRating, 5 stars2 months ago
We had a very peaceful stay at this rental home—just as described, and perfect for a relaxing recharge. It’s a great spot for a family getaway, and even our dogs loved it. Highly recommend!
Top Guest favourite
Chalet in Linden
4.95 out of 5 average rating, 44 reviews

Sky Island Chalet

LisaRating, 5 stars1 month ago
The view is beautiful! The main space is perfect for relaxing and visiting - but the bedrooms have enough space between them to provide some quiet and privacy for groups that have both early birds and night owls. Listening to the birds while sitting in the hot tub was especially relaxing, after attending a busy family gathering at a nearby winery.
Guest favourite
Chalet in Front Royal
4.95 out of 5 average rating, 134 reviews

Whitetail Summit - Shenandoah/hot tub/wineries

HeinrichRating, 5 stars2 weeks ago
We were a combined bunch of 8 adults and a 3 yr old. We had an incredible time, despite having a week of mostly rainy weather. There is plenty to do in the house and it is very comfortable. The kitchen is well stocked with small appliances and utensils. The house is kid-friendly and has all you need to entertain the kids and accommodate toddlers. The location is quiet and secluded, but close enough to a variety of attractions to keep you busy in good weather. We had a precious time and were sad to leave. Jenny was very communicative and responsive. She provided us with all the details we needed to enjoy the stay.
Guest favourite
Chalet in Davis
4.86 out of 5 average rating, 159 reviews

Big, Bright SLOPESIDE Ski Chalet, Outdoor Hot Tub!

ElydiaRating, 5 stars4 months ago
This place was AWESOME! Perfect location for wanting to spend your time on the slopes! Super cozy, very spacious, looks exactly like the pictures. The living area is a great hangout spot and the fireplaces kept us nice and warm during this windy winter stay.
Top Guest favourite
Chalet in Knoxville
5 out of 5 average rating, 62 reviews

4 King Suites | Hot Tub | FirePit | Arcade | Games

LaurenRating, 5 stars2 days ago
We had a great stay. The home was beautiful and incredibly peaceful; it was a great getaway from the city. The kitchen was absolutely gorgeous and stocked with everything we would need to cook. Highly recommend!
Superhost
Chalet in Basye
4.92 out of 5 average rating, 106 reviews

Luxury Moose Retreat- At Bryce Resort

ChristineRating, 5 stars3 weeks ago
This was a beautiful property tucked away in a quiet community. The home was very beautiful and clean. It was also spacious, yet cozy. The hosts gave detailed instructions about everything we needed. We didn't need to contact them about anything because we had no issues during our stay.
Guest favourite
Chalet in Gormania
5 out of 5 average rating, 20 reviews

Iron Ore Mountain Lodge

CristianRating, 5 stars5 months ago
Beautiful house to be with family and friends. Good spaces. Bedrooms, kitchen, living room We had a great time

Lakefront chalet rentals

Superhost
Chalet in Hidden Valley
4.81 out of 5 average rating, 104 reviews

Dillon's Getaway Chalet at Hidden Valley Resort

MichelleRating, 5 stars4 months ago
Our group of 13 which had 3 families with 7 kids really enjoyed this house. Our favorite part was the location to skiing. Although not officially a ski-in/ski-out, the slopes were within walking distance and much easier for our younger skiers to access. The house was clean, fully stocked and provided enough beds for our large group. Would definitely recommend bringing your 4WD vehicle if snow is predicted during your stay as the driveway is a little steep. We plan to book again for our next Hidden Valley trip!
Guest favourite
Chalet in McHenry
4.84 out of 5 average rating, 195 reviews

Drake's Nest on Deep Creek Lake

MakaiyaRating, 5 stars1 week ago
Jerry was an incredible host. He was very helpful and his home is nice and cozy. We loved every second of our stay. The dock was so beautiful. The home is even nicer in person. And the price is so affordable. We loved our stay. Thanks so much for the wonderful trip Jerry!
Guest favourite
Chalet in Swanton
4.83 out of 5 average rating, 60 reviews

Deep Creek Lake - Lakefront pup-friendly Chalet!

ConstanceRating, 5 stars4 months ago
Cabin and location is in a prime location right on the lake. My family went there on a weekend that was snowy, rainy, dreary. We could not do outdoor activities, so we drove to Walmart ordered food and had an amazing weekend in the cabin. Ample space, stocked kitchen, clean bathrooms, pool table, plethora of games, large dining room table where we had a ball! Very peaceful and relaxing atmosphere, made for great pictures. Paul is an incredible host. Responsive, honest, reliable. I highly rec this location and my family and I will return.
Guest favourite
Chalet in McHenry
4.94 out of 5 average rating, 32 reviews

Hartwood Haven - Steps from lake, boat slip & fun!

KevinRating, 5 stars2 weeks ago
This house felt like home from the second we walked in. Great location, walkable bars and restaurants, great dock, and just a wonderful place to escape to. Melanie was so kind and helpful, we can’t say enough great things about this experience. We will be back for sure!
Guest favourite
Chalet in Boswell
4.89 out of 5 average rating, 96 reviews

Peaceful Chalet in Laurel Highlands *Reduced Rate*

HannahRating, 5 stars3 weeks ago
Beautiful house on the lake. Loved waking up and hearing the different bird songs. Very much enjoyed the indoor and outdoor fireplaces. Comfortable room for everyone. Bathrooms were great, water pressure was fantastic, always a plus! Wonderful location, we ride at Mountain Ridge ATV park and it was a very easy drive (about 30 min) from the house to Mountain Ridge.
Superhost
Chalet in McHenry
4.85 out of 5 average rating, 190 reviews

R & R Retreat

CarolRating, 5 stars1 month ago
This was a great place to stay for a weekend fishing trip. The private slip and the great location on the waterfront was perfect. My brothers and I ended up catching 7 different species of fish, including several chain pickerel near the dock. Larry is a really friendly host, provides a ton of information about the area, and was always happy to offer up suggestions!
Guest favourite
Chalet in Mercersburg
4.94 out of 5 average rating, 112 reviews

Amazing Summer Holiday and Mountain Retreat

AndreaRating, 5 stars3 months ago
This is an excellent home for staying near the slopes! The beds were super comfortable, the welcome basket, kid friendly amenities, and provided essentials were very much appreciated. We would love to stay here again.
Superhost
Chalet in Basye
4.81 out of 5 average rating, 172 reviews

House over The Pond w/ Game Rooms, Views

ClaraRating, 5 stars3 weeks ago
My friends and I had a fantastic stay at a particularly beautiful home! the natural surroundings were unbeatable, and the architecture and design of the house made for great gathering spaces as well as private areas to relax. There was a small challenge with a few spots in the house that weren't cleaned properly, but the hosts were great about replying to my concerns and resolving the issue. I would definitely recommend this Airbnb, and I hope to return again!

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