Holiday rentals with a pool in Deep Creek Lake

Lakefront w Dock, Pool, & Courts

Welcome to Your Lakefront Retreat in Oakland, MD Escape to serenity at this cozy lakefront getaway tucked into Western Maryland’s peaceful mountains. Nestled just outside charming downtown Oakland, MD, in the Blakeslee Community, this retreat offers the perfect mix of lake-life, nature, adventure, and small-town charm — ideal for couples, families, or friends seeking a relaxing escape. This home is located in The Blakeslee ~ a well-maintained, private community known for its amenities which include an indoor pool, tennis courts and a playground. Access Details: Dock is located in the community docks (approx 200ft walk from the home), & has a designated slip for the home. Please note that docks are only guaranteed from Memorial Day through Labor Day. Community / Area Details: This home is located in the Blakeslee Community at Deep Creek Lake. Community Indoor Swimming Pool: Open Thurs.- Fri. 12:00p.m. - 8:00p.m., Sat.- Mon. 10:00a.m. - 6:00p.m.. Closed Tues. and Wed. The Space - Bright and comfortable living area with large windows offering great views of nature, the lake is only steps away - Fully equipped kitchen — great for whipping up local fare or relaxing breakfasts - Large living room with lake views - Large game room in basement - Dock slip - Comfortable bedrooms - A private deck or porch — morning coffee or evening stargazing awaits - Wi-Fi, heating, air conditioning, parking, are all available at the home. Why Guests Love Staying Here: - Proximity to Nature: You’re a reasonable drive from beautiful outdoor attractions — including Swallow Falls State Park, home to the stunning 53-foot Muddy Creek Falls and towering old-growth hemlock forests. - Adventure Nearby: Explore Garrett County’s trails in Garrett State Forest. - Relax & Unwind: Enjoy a picnic, fishing, or kayaking at Herrington Manor State Park, with its peaceful lake and scenic trails. - Small Town Vibes: Stroll through Oakland’s historic district, full of charming architecture from the 19th and early 20th centuries. - Outdoor Fun All Seasons: From leaf-peeping in autumn to snow activities in winter, this area truly transforms with the seasons. - Local Events: Time your stay right, and you might catch the Autumn Glory Festival, one of Oakland’s biggest seasonal celebrations. - Family-Friendly: Great hiking, nature, and kid-friendly spots nearby — including easy trails and state parks. Things to Do Nearby - Hike the trails at Swallow Falls for scenic waterfalls and forest walks. - Explore Herrington Manor State Park — swimming, boating, and relaxing by the lake. - Tee off at one of the nearby golf courses, multiple great 18-hole course surrounded by nature to choose from. - Visit charming shops, local restaurants, and historical sites in downtown Oakland. - Take a scenic drive along the Maryland Scenic Byways, winding through rugged terrain and forested beauty. Practical Details - Access: Keyless entry, your access code will be sent 24hrs before check in. - Parking: Ample parking for up to 4 cars - Nearby Essentials: Grocery store, gas stations, coffee shops, hospitals, are all within a 15 minute drive. - House Rules: Quiet hours are daily 11PM-8AM. Why This Place Stands Out: This is not just another lakefront rental — it’s a thoughtfully located hideaway, located on the lake with a dock slip. Whether you're here to hike, relax, or explore Garrett County’s natural and historic gems, this home gives you a peaceful base. Come unwind, recharge, and make memories. 4WD is required for Winter months (Nov - Mar).

Multi-Family Cabin: Huge Yard + Resort Perks!

Charming chalet-style cabin in a 4-season community for outdoor enthusiasts. Nestled in a quiet wooded area in the mountains of Alpine Lake Resort, WV. WiFi great for virtual work! Family/friends have plenty of room;4+ BRs, family rm, comfy loft, cathedral ceiling, game room, fire pit, spacious yard for group games. Walk 6 blocks to the Lake's beach, paddling, fishing, tennis, basketball & 1.5 mile to workout gym, indoor heat pool, golf, mini golf, XC ski. 19mi to DeepCreek Lake, WISP Ski & more

Hot Tub By Fireplace / Firewood/Pool Memb./Lg Deck

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.

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.

8 BR, HotTub, Sauna, Ski-In/Out, Limo Golf Cart MD

The new Lakeview Luxe Estate (named for it’s stunning views) is where the dream, group vacation experience comes together through the eyes of an award-winning developer and engineers. This 8 bedroom mansion is the latest iteration in a series of ultra-luxurious group vacation homes that the dream team has designed. Luxe is nearly identical to our Aurora Point Chateau property at Timberline Resort - which books up months in advance and has received rave reviews - but this home is even Grander!

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!

Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs

Escape to our charming Hemlock Cabin, nestled among the trees & designed for ultimate relaxation. Just a 1/4 mile from local restaurants & shopping, you'll enjoy the perfect blend of nature & convenience. This brand new cabin features 2 cozy BRs, full kitchen, hot tub & a modern bathroom, making it ideal for families or a getaway with friends. Access to Starlink WIFI and YouTube TV keeps you connected. And don't forget, we're dog-friendly, so your furry companions can join in on the adventure!

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!

4 Seasons Wisp- Lake Access, Hot Tub, AirCondition

This renovated, dog-friendly spacious Ski-In/Ski Out townhome is minutes from Wisp Resort's Lodge, nearby restaurants, and shops. Deep Creek Lake activities are all within a few minutes. The home has access to the "Down Under" ski trail and comes with lake access via a private lakeside park just a short walk or drive from property. Guests also have access to the Garrett College Community Aquatic and Recreation Complex(CARC) Gym and Pool during their stay. Must have AWD/4WD in winter.

Lake access, 3 suites, hot tub, outdoor 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!

New! The Butterfly Suite 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 our 825 sq. ft suite as you melt your cares away in front of the fireplace. 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 a couple's romantic escape!