USA Appalachian Mountains Maryland Oakland Listing #120475

Big Boulder Retreat - Oakland, MD

Max. occupancy: 5 2 queen beds, 1 double sofa bed 2 bedrooms 1 bathroom No pets  4WD/traction may be required in winter
Address provided after booking

Worry-free booking

Enjoy peace of mind with simple cancellation and optional travel insurance. Learn more >

Expert cleaning

Pro housekeepers clean thoroughly and provide fresh linens before every stay.

Local support

Count on 24/7 guest care and local teams everywhere we operate.


Smart locks or lockboxes at many homes offer smooth, contactless check-in.

Peaceful centrally located home near summer and winter outdoor activities

Escape to this charming cottage in Oakland, MD, nestled on a dead-end street for ultimate peace and seclusion. With exposed beams and a cozy atmosphere, this super cool retreat is the perfect spot to get away from it all. Step outside to enjoy the firepit behind the house, ideal for roasting marshmallows under the starlit sky.

Just a short 15-minute drive away, you'll find the town with restaurants, a seasonal farmer's market, as well as the fascinating B&O Railroad Museum. Nature enthusiasts will delight in the proximity to Swallow Falls State Park, Herrington Manor State Park, and Sang Run State Park, offering waterfalls, hiking trails, swimming, canoeing, and kayaking experiences.

Surrounded by Garrett State Forest, this property is a haven for hikers with its rock maze trail and scenic beauty. For water recreation and outdoor adventures, head to Deep Creek Lake, only 25 minutes away, where you can enjoy canoeing, kayaking, hiking, and dining at waterfront restaurants.

Make your way to Wisp Ski Resort, also just 25 minutes away, for skiing and snowboarding in the winter, as well as summer festivals, obstacle courses, and a mountain coaster. Thrill-seekers can try the man-made white water rafting adventure at the top of the mountain. For more adrenaline-pumping fun, embark on a whitewater rafting excursion on the Youghiogeny River.

Back at the cottage, relax in comfort with amenities like a gas fireplace, internet access, and a washer/dryer. Enjoy outdoor gatherings on the deck with patio furniture and a gas grill, or cozy up indoors with board games and Netflix streaming. Whether you're seeking adventure or a peaceful retreat, this centrally located home offers the best of both worlds.

Things to Know

This Vacasa Guestworks vacation rental is operated and managed locally by an independent host.
Prior to your arrival, you will receive local host contact information, who will manage your guest reservation. Your local host will provide in-stay support, secure entry, and arrange pre- and post-stay housekeeping services.
If you need anything during your stay, the home’s independent local host is ready to help 24/7! Guestworks is a service offering of Vacasa that allows homeowners to smoothly and efficiently manage their own properties.

You must be 25 years or older to rent this property.



Washer/dryer : Private

Heating & cooling

Central AC


Partial AC

Gas fireplace

Kitchen & dining








Wireless router

Netflix streaming

Nearby activities & attractions

Downhill Skiing

Golf nearby

On-site activities

Board games


Gas grill : Private



Map showing the location of the Unit

0 reviews

Be one of the first to experience this new Vacasa listing. Our local team has the home clean, stocked, and ready for your stay. Even better, we'll be on hand with 24/7 support to make sure your stay is seamless.

What guests say about Vacasa

1 million+

5-stars reviews

9 / 10

Guests would likely recommend Vacasa to a friend

4.5 / 5

Average clean score