Holiday rentals with a pool in Garrett County

Deck Fireplace+Firewood/Pool Memb/ Private &Serene

LAZY BEAR LODGE AT DEEP CREEK LAKE (3200 sq. ft.) Need some quality time away but want to avoid crowds & still be close to everything at the Lake? Secluded & private on 3 acres in a serene forest of hemlock trees & boulders, this natural space is calming & architecturally pleasing for the soul! Cares slip away with the smell of a real wood fire, rustic décor, warm color paints, stone and wood. HotTub by fireplace on deck. CARC membership, lots of firewood and extras. Large private sledding hill!

Our Lovely Lake Retreat

Spacious 3 bedroom, 2.5 bath townhome with gorgeous views of Deep Creek Lake and WISP ski slopes. The newly updated townhome sleeps 8 comfortably. You will enjoy the air conditioning, fully equipped kitchen & grill, wood burning fireplace and 4 smart TV's. 15 steps up to entrance. Neighborhood amenities: indoor community pool, picnic tables, dock and a beach/sand area (kids will love). Level lakefront access right across the street. Min age to rent 25. Max 3 cars. HOA rule: no trailers/campers.

Oakland Bear Lair|7BR Luxury Log|Pool, Hot tub

Oakland Bear Lair is just minutes from Deep Creek Lake and Wisp Resort in Oakland, MD. Skiing, boating, hiking, year-round outdoor adventure. A spacious 7-bed, 4-bath log cabin retreat near Deep Creek Lake & Wisp Resort. This pet-friendly, 'bear' themed cabin comfortably sleeps 18+ guests, with a fully equipped kitchen, game room, pool table, hot tub, seasonal heated pool, outdoor fire pit, EV charger. Ideal for large family vacations, group getaways, or remote work in a serene, wooded setting.

Lakefront! IndoorSauna! HotTub! Sleeps 14! Kayaks!

Welcome to the Lucky Penny! Enjoy this gorgeous lakefront home at Deep Creek Lake! 5 bedrooms, 3 primary suites, kids room with arcades, and room for 14 guests. Enjoy a large brand-new deck overlooking the lake with hot tub, fire pit by the water, kayaks and canoe for guest use, private dock access (May-Sept), indoor sauna, commercial ice maker, and Margaritaville machine. Just 1.5 miles to Wisp Resort + CARC access (pools & gym) a short 10 minute drive. Perfect for families and group escapes!”

NEW~Indoor Pool & Hot Tub~Game RM~Near Wisp~Dock!

The Big Dipper - Brand new construction with seasonal lake views & everything for your DCL vacation. The perfect, all suite, 5 bedroom (including bunk room), INDOOR POOL cabin with a HOT TUB, fire pit, game room (pool table, shuffleboard & arcades), outdoor living room & fireplace, EV charger and more! Less than 5 minutes to Wisp Resort (Skiing), Lodestone Golf Course, marinas, grocery store, restaurants & across the street from DCL & dock space. ✔ READ House RULES - Deposit HOLD required

Lake View | Hot Tub Pool Gym & Games | EV Charger

5 min to Wisp Resort, lake, marinas, dining, hiking & state parks. Access to community indoor pool, pickleball, and gym. 🛏️ Sleeps 10 (4x queen, twin sofa bed in den, twin futon in loft) ♨️ Hot tub 🌲 Partial lake views 🔌 EV charger 🏊 Community indoor pool, pickleball & gym 🎱 Pool table & shuffleboard 🔥 Fireplace & outdoor fire pit 🍔 Grill + full kitchen ☕ Keurig & drip coffee maker 📺 TV in every bedroom, den & great room 📶 Fast WiFi 🐾 Dog-friendly ($189 fee) 🚗 Park 5–6 cars or boat

Amazing Views! | 4BD/4.5BA | Dock, WISP, Hot Tub

Get away from it all! Our home features four large bedroom suites, two spacious family rooms, elevated deck lake views, and a boat slip. And pets are welcome! Nestled on a wooded hillside, you will love the feeling of seclusion while still being central to all DCL activities. We offer a new kitchen and comfortable home furnishings that invite you to unwind. Gather around the fireplace, relax in the hot tub, get on the lake, or step outside onto the deck, and enjoy that fresh mountain air!

Escape to Wisp Mountain

✨ Escape to Wisp Mountain! ✨ Your mountain adventure starts here. New Log Home built in 2022. ⛰️ Minutes from Wisp Resort, Lodestone Golf, Deep Creek Lake & state parks—perfect for skiing, hiking, paddling, or relaxing. 🔥 After a day out, unwind with: • A bubbling hot tub under the stars • A crackling fire pit & fireplaces • Pizza oven + grill for epic feasts • Spacious king & queen bedrooms Bring your crew, make memories, and experience the best of Deep Creek living. 🏔️

Lake & Pool Access, 3 suites, hot tub, fireplace

Welcome to West Oak! Tucked among towering trees, this welcoming retreat is designed with great vacations in mind. Three roomy suites, high-end furnishings and finishes, a hot tub, and an outdoor fireplace are just a few highlights. Lake access for swimming and fishing and a boat slip are within walking distance. On top of all that, it is within minutes of skiing, state parks, golf, marinas, dining, and more. Experience the ultimate Deep Creek vacation when you book West Oak!

DCL Cabin Updated Baths, DOCK SLIP & Fire Pit

Bring the whole family and enjoy a large level lot with a firepit and cornhole boards. Your dock slip is a short 2 minute walk with a beach cart to help get all your necessities to the lake! Come back and hangout on the back deck with space to conversate, BBQ and dip in the hot tub! The loft has an oversized beanbag and foosball table along with two separate living areas! End the night in front of the large stone wood burning fireplace watching a movie!

LakeView Boathouse - 6 bedroom boat slip home

Welcome to LakeView Boathouse, a peaceful mountain retreat with stunning lake views. This family-friendly home features 6 bedrooms, 4 bathrooms, and sleeps 16+ guests. Enjoy lake access, a private boat slip, walking/hiking trails outside your door, and a gated community with a large playground for kids. Guests also have access to the neighborhood pool open Memorial Day through Labor Day. Guests must confirm that boat slip is available before booking.

New! The Board Room at Enchanted Table Meadow

Minutes from Wisp Ski Resort & Deep Creek Lake! Come as you are & take a seat at nature’s table under the canopy of stars. Embrace the wooded ambiance and meadow views from the Board Room & living space. Located between I-68 and Deep Creek Lake/Wisp. Our hope is to provide a serene landscape where you can find peace and rest through nature. Our setup works well for business travelers & as an escape to nature in lieu of hotels!