• 8 Bedrooms

  • 8 Full & 3 Half Bath

  • 20 Guests

  • 6300 Sq Ft Home

Enjoy The Great Outdoors Lakeview Vacation Rental Home in Deep Creek Lake, MD

The Crooked Oak Lodge is a dark, majestic 8-bedroom Deep Creek retreat tucked into the gated Waterfront Greens community. Two features set this home apart from anything else on the lake: a private heated indoor pool open year-round, and a hidden speakeasy bar tucked away off the lower-level game area — a true clandestine cocktail spot with a roaring-twenties soul. Every bedroom has its own ensuite bathroom. The great room rises into cathedral ceilings around a floor-to-ceiling stone fireplace and plush leather furnishings.

Built for large families, milestone trips, and groups that want luxury without compromise — and yes, well-behaved dogs are welcome.

The hidden speakeasy bar is the talk of every guest who stays here. Tucked off the lower-level game area, it’s a step back in time — perfect for crafting cocktails and sophisticated entertaining with a dramatic reveal that newcomers never forget.

The private indoor pool runs year-round, climate-controlled, with its own powder room for convenience. Snow falling outside? Doesn’t matter — swim anyway. The pool is one of the defining reasons guests rebook this property: it turns Crooked Oak into a true four-season home.

This 6,200 sq ft lodge spans three levels with bedrooms thoughtfully distributed across all of them. Eight private suites — seven kings and one bunk room — each with its own ensuite bathroom. The main level holds the heart of the home: the gourmet kitchen, dining room, and indoor pool. The upper level adds three more king suites plus a loft with a queen sleeper sofa. The lower level is where things get fun: a den, game area with pool table, the hidden speakeasy bar, and two more king suites.

Granite kitchen with gas stove and full appliance package. Indoor dining seats 8, breakfast bar seats 6, plus outdoor decks for fresh-air dining. Fast WiFi, multiple TVs, central air, and laundry on the lower level.

The deck wraps around the home with mountain views and seating areas on both upper and lower levels. An outdoor hot tub waits for evening soaks under the stars. The fire pit handles late-night s’mores and fireside conversations. For lake days, a private boat dock slip may be available for an additional fee (book at time of reservation, first come basis; guaranteed Memorial Day through Labor Day).

Swanton, MD

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Connect with Nature - Deep Creek Lake, MD

The Crooked Oak Lodge sits in Waterfront Greens, one of the most sought-after gated communities at Deep Creek Lake. Inside the community: a par-3 golf course, mini-golf, a catch-and-release fishing pond, tennis and pickleball courts, basketball, canoe and kayak station, sledding hill, paved walking paths, and gazebos overlooking the pond.

Beyond the gates, Wisp Resort is about 17 minutes away with skiing, snowboarding, tubing, the mountain coaster, zip-lining, and ice skating. Deep Creek Lake State Park and Swallow Falls State Park (home to Maryland’s tallest waterfall) offer miles of trails. Golfers have Thousand Acres Golf Club with lake and mountain views, Lodestone, and Fantasy Valley at Wisp Resort. The downtown Deep Creek area handles restaurants, shops, and grocery stores.

  • Community Amenities Like Golf & Mini Golf
  • Lake Access Property
  • Hidden Speakeasy Bar
  • Private Indoor Pool*
  • Private Hot Tub
  • Arcade Games, Pool Table & Shuffleboard
  • Dogs Allowed*
  • Free WiFi & Cable

*Additional charges may apply for pool heating & pet fees. Call or email us for more information.

Enjoy Your Stay in Crooked Oak

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Experience All Deep Creek Has To Offer

One of a Kind Hidden Speakeasy Bar

Spacious Interior For The Whole Family

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