Holiday rentals with a pool in Garrett County

4.95 out of 5 average rating, 246 reviews

The lodge features a striking architectural design with a wooden ceiling and stone accents, surrounded by a forest backdrop. A large deck with wooden railings extends from the structure, providing a welcoming entrance to the space.

Home in Oakland

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!

FamilyValueComfort

5 out of 5 average rating, 102 reviews

An inviting open-concept living space is highlighted by vaulted ceilings and ample natural light. The kitchen features modern stainless steel appliances and a spacious island. A comfortable seating area with a leather couch and stylish decor is situated nearby, enhancing the home's welcoming ambiance.

Townhouse in McHenry

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.

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Guest favourite

Cabin in Oakland

4.95 out of 5 average rating, 20 reviews

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.

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The cabin's exterior is illuminated at dusk, showcasing a modern design with a combination of stone and timber. A spacious deck wraps around the structure, providing access to outdoor living areas. The image emphasizes nearby lake views, enhancing the cabin's serene environment.

4.83 out of 5 average rating, 41 reviews

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

LocationFamilyAmenities

4.84 out of 5 average rating, 44 reviews

The cottage features a rustic wooden exterior surrounded by vibrant autumn foliage. A hot tub is positioned on the deck, and soft lighting illuminates the space. Stairs lead to the upper level, enhancing the cozy mountain retreat ambiance.

Cabin in McHenry

Cozy Cottage | Fire Pit, Pool, Theater & Game RM

Escape to Cozy Cottage by the Slopes, a family-friendly retreat with pool, theater room, and game room. Sleeps 8 with 3 bedrooms and 2 baths. Minutes from Wisp Resort and Deep Creek Lake. Enjoy a fully equipped kitchen, cozy living space, Wi-Fi, and all the comforts for a fun mountain getaway. Note: The property is shared with Cozy Cabin by the Slopes and may be occupied during your stay. This property has year round community pool access at GC CARC – Community Aquatics & Recreation Complex.

FamilyValueAccuracy

4.87 out of 5 average rating, 111 reviews

The exterior of the Craftsman-style home features a welcoming front porch with wooden rocking chairs. Lush green shrubs and blooming flowers add color to the landscape, while a spacious deck is visible in the background. A stone path leads to the front entrance.

Home in Oakland

Spacious Home Near All Deep Creek MD Has to Offer

Nearby endless opportunities to explore the area, including, skiing, hiking, boating, swimming and nightlife, Wine Down offers the perfect basecamp for every member of your crew with inviting Craftsman-style elements and noteworthy amenities both inside and out! The open concept on the main floor and the rec room on the second floor takes the effort out of entertaining guests of all ages. No matter how you choose to unwind, Wine Down will surely make your Deep Creek vacation one to remember!

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Guest favourite

4.78 out of 5 average rating, 9 reviews

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

LocationFamilyComfort

4.96 out of 5 average rating, 294 reviews

Home in Oakland

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!

LocationFamilyHiking

5 out of 5 average rating, 10 reviews

NearWISP| Luxury Log Home| Hot Tub| DockedN'Loaded

"Docked N' Loaded" is your spacious 5-bedroom, 4.5 bathroom luxury log retreat built for unforgettable getaways. Tucked inside the prestigious gated community of Deep Creek Highlands, in the heart of McHenry, Maryland. This retreat is 2 miles from Wisp Resort & with your dock slip on Deep Creek Lake, adventure is always within reach. Between the hot tub, pool table, and foosball, you'll never run out of ways to unwind together. This is the trip your group will talk about for years to come!

LocationFamilyNearby

A newly built log home features a natural wooden facade, complemented by a covered porch with seating. Surrounding landscaping includes carefully arranged rocks and native plants, creating a harmonious outdoor environment. Large windows invite natural light into the home, enhancing the rustic aesthetic.

4.94 out of 5 average rating, 50 reviews

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. 🏔️

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Guest favourite

A spacious sleeping area features a large bed adorned with a quilted cover and decorative cushions. A wooden accent wall with soft lighting complements the neutral decor. A window framed by dark curtains offers a view of the outdoor greenery, enhancing the room's inviting atmosphere.

Guest suite in Accident

4.97 out of 5 average rating, 224 reviews

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!

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