Vacation rentals with a kayak in Garrett County

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).

Mad Men Lake House*LAKEFRONT*Fam&Dog Friendly*OUTDOOR MOVIE EXPERIENCE*HOT TUB*1.8mi to WISP*WORK SPACES*wood CRIB!

NEW BUILD HOME! Wow! Deep Creek has never seen anything like this before! It's a one-of-a-kind experience that gives you all the amenities you need for your BEST vacation/getaway/staycation ever! With it's unique combination of rustic look and modern features, it will surely delight every guest! After a fun-packed day on the lake, fishing or boating, unwind on our upper deck as you watch and hear the water lap up on the shore with a refreshing drink in hand. Or are you just getting back from an invigorating day on the slopes? Relax those muscles in our lower-deck hot tub, gazing at the stars in the winter sky above! You get the best of the lake and the mountain in this dog-friendly hidden gem! Imagine evenings enjoying the mountain breeze as you roast marshmallows in our fire pit! Or cozy up in front of the gas fireplace in our open-concept great room that allows everyone to be together. Fish and swim from our private dock or use it to moor your own boat or jet-skis. Witness spectacular sunrises as you take an early morning paddle with our kayaks and 2-person canoe. Enjoy a well-lit, private work space with high-speed internet to facilitate your virtual work needs. A real wood CRIB and 2 pack and plays are provided too! Plus, we offer an OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best vacay EVER! NOTE: All Wheel Drive cars/suvs are necessary in winter months due to steep driveway.

A "Sweet Escape" at Deep Creek and Wisp Ski Resort

Welcome to Sweet Escape, a charming 4-bedroom, 3-bath chalet nestled in the peaceful hills of McHenry, Maryland. Sleeping 10 or more guests, this spacious retreat offers stunning views of Wisp Ski Resort and is just minutes from beautiful Deep Creek Lake. Enjoy a tranquil country setting with cozy living spaces, a fully equipped kitchen, and inviting outdoor areas perfect for relaxation. Whether you’re seeking adventure or quiet moments in nature, a perfect getaway in the heart of the mountains.

LakeAccess 4BR DeckSlide OD Movies HotTub Kayaks

Our redesigned 4 bedroom cabin with modern finishes & amenities creates amazing family experiences: - Wisp - 8 Min, 4.1 Miles Away - Deck Slide & Swings - 2x 100" Outdoor Movie Screen & Bluetooth Projector - 7 Person Hot Tub - Fire Pit w/ Comfortable Seating - Playstation4, Pac-Man, Shuffleboard - Well-Equipped Kitchen, Propane Grill - 350ft to Lake/Beach/Swimming - 1 Person & 2 Person Kayaks & Paddleboard - Roku HDTVs - All Rooms - Pro Wifi System - 600+Mbps Great for Remote Work - EV Charger

Til Valhalla II

Welcome to our charming Cape Cod on a very private hill, surrounded by 2+ acres of wildlife, trees and serenity. The covered front porch is where your entrance is located. Park out front. Unlock your door by using a key code. Welcome to your private and secure home away from home. The stairs lead to a bright and clean four room suite. Consisting of a fully stocked kitchenette, full bath, king bed, XLG twin bed and rec room with a workstation, breakfast bar, and comfy seating. Separate heat/air.

Lakefront Cabin in Stunning Storybook Setting

Reconnect with nature, relax, recharge, & rejuvenate. Our newly updated cabin & incredible setting is just what you need. Lakefront views with boat slip, kayak, hot tub & more. Come enjoy this one of a kind home for fishing (a trout brook runs through our property), bird watching, meteor showers, boating, foliage, horseback riding or skiing (10 mins from Wisp). Within mins you’ll find: hiking, ATV riding, white water raffling, countless farms & restaurants & more. IG page at CampLittleBearMD.

Family A-Frame | Kayaks Included | Deep Creek Lake

Designed for families dreaming of starry skies, campfire s'mores, and waking up to birdsong. Welcome to your peaceful retreat near Deep Creek Lake. A place where daily life fades into nature's backdrop and connection with loved ones comes effortlessly. Built in 2024, thoughtfully furnished to blend modern luxury with rustic charm, on 2.5 wooded acres. Spring hikes & waterfalls. Summer kayaking on the lake. Cozy fall firepits. Winter snowball fights. Your family's escape for every season.

Cozy Chalet @ Pond's Edge - Comcast WiFi -Wisp/DCL

Escape! Be refreshed at Country Acres Retreat on the former Country Acres Strawberry Farm. Minutes from Deep Creek Lake, the cozy cabin is nestled among white pine trees and overlooks a 1.5-acre pond stocked with bass. Wake up with nature and a cup of hot coffee as the mist ascends over the water. Listen to the whisper of the summer breeze among the pine trees as they carry your cares away! Perfectly suited for a reunion of old & new friends, a family gathering, or a romantic getaway!

Hot Tub, Game Room + Fire Pit, Great Location!

🎉 Discounts - Save 8–10%! Book 6+ months ahead, stay 1+ weeks! ✅Within walking distance to the lake! ✅Pool Table, darts, multipurpose game table, board games, cards. ✅Plenty of parking ✅Lake access from the neighborhood dock are extra perks!*cozy beds ✅large deck ✅Hot Tub ✅Huge dining table ✅Make s'mores at the firepit ✅Quiet neighborhood ✅Relax/watch the wildlife walk through yard. ✅TVs in every room provide entertainment for all! ✅Fast, reliable WiFi (444 Mbps down / 117 up)

Elegant Home Away: Hot Tub/Game Room/Kid-Friendly

The perfect location for your deep creek escape! Enjoy a quiet retreat in this custom-built oasis near the golf course. Amenities galore: ping pong, foosball, arcade HeadsUp poker, disc golf, basketball, golf driving net, kids’ tree fort and play room! Relax by the gas fireplace or in the hot tub after a day of hiking/skiing. Easy access to the fun of Deep Creek (<10 min to Herrington/Broadford, 2 min to historic downtown, easy drive to DCL/Swallow Falls/WISP ski resort)!

Deep Creek Aframe : Lake View, Dock slip, Hot Tub

Welcome to our recently built A-frame, set among the trees with beautiful views over Deep Creek Lake. Large windows fill the open-concept space with light, making it a relaxing, modern retreat. While this is not a lakefront home, the views are stunning. Our dock slip is 5 min down the road at High Mountain Sports; the state park, with swimming and kayak launches, is 12 min; and Wisp skiing/snowboarding is also 12 min. Coffee and Brenda's Pizza just 5 min. A central spot.

Dogs OK, Hot Tub, Lake Access, Dock Slip, Fire Pit

Tucked among the trees, Maple Ridge is a new home designed for incredible Deep Creek Lake vacations! Two roomy living areas offer great gathering space, and four suites give everyone much appreciated privacy. Unwind on covered porches or in the sauna or outdoor hot tub. Your lake access and dock slip are within walking distance, so it is easy to enjoy swimming, fishing, and boating. Plus, favorite activities like skiing, golf, ziplines, and white-water rafting are nearby!