Holiday rentals with a kayak in McHenry

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Top-rated Accommodation with a Kayak in McHenry

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Guest favourite

Cabin in McHenry

4.96 out of 5 average rating, 140 reviews

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.

Guest favourite

Cabin in Terra Alta

4.91 out of 5 average rating, 140 reviews

COZY CABIN in Alpine Lake Resort; 4 Season Getaway

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

Top Guest favourite

Cabin in Oakland

4.97 out of 5 average rating, 38 reviews

Cabin Gem: Hot Tub, Sauna, Central, Lake Access

Nestled among the towering trees and serene nature of central Deep Creek Lake, our cozy cabin, Trees Company, is a carefully designed sanctuary for relaxation, connection, and adventure. This snug retreat offers a perfect balance of vintage charm and contemporary comfort for small groups. Designed with wellness in mind, refresh your body and spirit with the private hot tub, 2-person sauna, fire pit, and inviting conversation areas tucked amidst the trees. Come and simply: Relax. Unwind. Enjoy.

Top Guest favourite

Holiday home in Oakland

4.97 out of 5 average rating, 117 reviews

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.

Top Guest favourite

Condo in Oakland

5 out of 5 average rating, 25 reviews

Landlocked@DCL Lakefront with Dock

Discover *Landlocked* at Deep Creek Escape to a cozy lakefront condo at Deep Creek Lake, nestled in the historic Red Run Condos. Enjoy stunning lake views, direct access to the water, and amenities like a private dock, pool, and tennis courts. Just minutes from Wisp Ski Resort, Lakeside Creamery, and top restaurants. Relax by the indoor fireplace or the lakeside fire pit. Perfect for families, couples, and adventurers alike. Experience the best of Deep Creek from your serene, modern retreat.

Top Guest favourite

Farm stay in Terra Alta

5 out of 5 average rating, 22 reviews

Pachamama’s Garden

Escape to Pachamama's Garden, a magical 41-acre organic farm nestled in the misty Appalachian mountains near Deep Creek Lake, Wisp Resort, and bordering Cranesville's 1600-acre Nature Preserve. The breezy penthouse apt with breathtaking 360 views. Bag the city life and reconnect with nature. Walk the fields and feel what it takes to be a natural farmer and work with Mother Earth. Wake up to a real farm-to-table experience with breakfast and cold-pressed Juices customized by a nutrient Chef

Guest favourite

Townhouse in McHenry

4.94 out of 5 average rating, 64 reviews

Adventure Cove Lakefront with Dock

Adventure Cove (AC) is in a charming centralized location of Deep Creek Villages for all season activities. AC is lakefront W/Dock and directly across from Wisp resort that provides multiple family activities. AC provides 1 single kayaks, 1 double kayak, 1 paddle board, 2 bicycles, 2 tennis rackets and light fishing gear. AC is set to house 8 people. Initially it was a 2 bedroom + nursery that was converted into 3 bedrooms + nursery for privacy. Please enquire for boat slip availability.

Guest favourite

Cabin in Accident

4.96 out of 5 average rating, 73 reviews

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!

Guest favourite

Cabin in Accident

4.96 out of 5 average rating, 118 reviews

Private Pond Access! Covered Hot Tub with TV!

POND ACCESS! Relax with the whole family at this peaceful cabin nestled in the pines! Enjoy soaking in the hot tub overlooking the pond, going fishing, swimming, canoeing, taking advantage of the large lawn, or just relax while taking in the view. Spacious outdoor area with string lights, gazebo, and fire pit. FIREWOOD PROVIDED! Our goal for Whispering Pines Cabin is to help you escape from the busyness of life and unwind in a quiet, peaceful setting with your family and friends.

Top Guest favourite

Home in Oakland

5 out of 5 average rating, 50 reviews

Central Perk-Mountaintop Escape

Welcome to our 3-bedroom, 2-bathroom vacation home nestled in the heart of Deep Creek Lake! Centrally located, the spacious and cozy interior features modern amenities, a fully-equipped kitchen, and a comfortable living area, perfect for unwinding after a day of adventures. Step outside onto the private deck with propane fire pit table, or gather around the lower fire pit for s’mores. Whether you're seeking water sports, hiking trails or skiing, this is your ideal getaway.

Top Guest favourite

Home in Terra Alta

4.99 out of 5 average rating, 129 reviews

Lake View Home w/Fire Pit, Indoor Pool, Dogs OK!

Woodhaven at Alpine Lake Resort is situated on a quiet, dead end street and offers beautiful views of the lake and surrounding woods. The house sleeps 10+ - perfect for two families or a group of friends. Reclaimed barn wood floors, 2 fireplaces, lots of games and puzzles, down comforters on all beds, high-speed wifi, DirecTV, Sonos music system, use of kayaks, canoe, 2 SUPs, fishing poles - everything you need to enjoy a peaceful and fun getaway in the mountains!

Guest favourite

Cottage in McHenry

4.97 out of 5 average rating, 63 reviews

Making Memories at the Lake

This cozy cottage is lake-front, within walking distance to ski slopes!! Just a short drive from numerous restaurants and cafes, nightlife spots, adventure filled activities, shopping, movies, and golf. Guests will have access to a kayak, canoe, charcoal grill, picnic table (in storage area) and fire pit. Inside, the home is comfortable, board games and puzzles are available. Family room has a new 42” TV, master bedroom also has a TV, WiFi is provided.