Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite

Townhouse in McHenry

5 out of 5 average rating, 42 reviews

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.

Guest favourite

Home in Thomas

4.97 out of 5 average rating, 73 reviews

Bears Lair,walk to PurpleFiddle! Canaan,Blackwater

The whole group will enjoy easy access to everything from this centrally located place. Within walking distance to Front Street where you'll find great food and local artisan shops. Canaan Valley Resort , Black Water Falls, Dolly Sods and Rails to trails are just a few of the attractions near by. This cozy 2br, 2 bth home offers a spacious deck and grill, open floor plan, stocked kitchen, dining area, and comfortable living room that features a gas fireplace, big screen tv and WiFi streaming.

Guest favourite

Home in Oakland

4.96 out of 5 average rating, 237 reviews

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!

Guest favourite

Cabin in Confluence

4.97 out of 5 average rating, 235 reviews

Cozy Mountain Cabin, Near Ohiopyle, Hot-tub

Planning your next getaway? Look no further than Lakeview Mountain Escape. Wake up to a breathtaking sunrise that overlooks the Youghiogheny Lake. We are conveniently located 3-miles from the Youghiogheny Dam and boat launch. Looking for an adventure? We are 4-miles from the Youghiogheny River Trail (part of the Great Allegheny Passage)and 12-miles to Ohiopyle State Park. Test your endurance on one of the many hiking trails, take a guided rafting tour or kayak down the Youghiogheny River.

Guest favourite

Townhouse in McHenry

4.95 out of 5 average rating, 21 reviews

Villa Celeste - Deep Creek Lake, MD

This well-maintained condo has lake and mountain views! Catch amazing sunsets nightly from the deck bar! Two of the 4 bedrooms are primary suites, one on the main level and one on the upper level. With almost 2500 square feet there is room for everyone and amenities galore. Conveniently located to everything Deep Creek has to offer. It's less than a quarter mile from multiple restaurants, shopping & marinas. Love to ski or play golf? It's less than 2 miles to Wisp Ski & Golf Resort.

Guest favourite

Cabin in McHenry

4.91 out of 5 average rating, 69 reviews

Mountain Life

Escape to Mountain Life's perfect mountain lake getaway! Our brand-new cabin offers stunning views of the lake, slopes, and city. Unwind in the hot tub, soak in breathtaking scenery, and enjoy the view from the porch. Located in the heart of the Deep Creek Lake area on Wisp Mountain, our prime location ensures easy access to activities, with the Wisp just 3 minutes away. This Airbnb, transferred by the previous owner, has received 86 reviews and boasts an impressive 4.97-star rating!

Guest favourite

Home in Swanton

4.94 out of 5 average rating, 18 reviews

Renovated Home with Dock, HotTub, Golf DogFriendly

Recently renovated, this beautiful home sits on a hillside in the Waterfront Greens community. Stunning views, privacy, great location, and many amenities make it the perfect choice. The new deck has plenty of seating & some of the best views around. Waterfront Greens offers a par 3 golf course, mini golf, tennis, lake access and the dock area. One of the best locations in the area for safely walking & riding bikes. Please note that there is a pet fee (for up to 2 dogs) of $200.

Superhost

Cabin in Swanton

4.8 out of 5 average rating, 94 reviews

"Whispering Pines"

Soft greens and powder blues adorn the interior and blend seamlessly with the lush natural setting of "Whispering Pines." The home is conveniently located within minutes of the State Park and could be the perfect place to gather for your next family vacation destination! You’ll love my place because of the views, the location, the ambiance, and the outdoors space. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets).

Superhost

Chalet in Oakland

4.91 out of 5 average rating, 128 reviews

Spectacular Chalet, Timroc II, close to lake, Wisp

ENJOY every season!! Short walk to the lake and dock! ! 15 minute drive to Ski Wisp! Fire pit, decks and screened in porch! Relax in the hot tub, enjoy family and/ or friends time and just get away from it all! 5 comfortable sized bdrms, each with large windows letting in natural daylight. First floor master, hardwood flooring throughout, many sliders for easy access. Finished bsmt with pool table, separate bdrm, full bath and laundry! DON'T SEE YOUR DATE, PLEASE CALL!

Guest favourite

Home in Oakland

4.91 out of 5 average rating, 68 reviews

Serene Mountain Escape: Hot Tub, Foosball, Views!

The perfect location for your escape! At this serene home right in the heart of the Deep Creek Lake area you’ll wake up in paradise to snowy mountain views. Enjoy easy access to Deep Creek Lake State Park, Herrington Manor, Swallow Falls, Fork Run…Settle in after a long day of hiking or skiing in the mountain-view hot tub or in front of the gas fireplace. Family/pet friendly with foosball, air hockey, toys, bounce house/pump, sledding in the yard!

Guest favourite

Condo in Oakland

4.91 out of 5 average rating, 79 reviews

Top Notch Lake Getaway - Cozy in a plush resort

Complete remodel and upgrades in Nov 2022. Unique space and a great getaway; 2 separate sleeping areas. Spacious +BR w/loft nestled on the shores of Deep Creek Lake, professionally furnished w/onsite mgmt, King bed in private bedroom w/closet, Queen bed in loft area, propane fireplace, kitchenette with microwave & full size fridge, keurig, full bath lower level, vaulted ceilings and much more. Community fitness center. Please, 25yo to rent.

Top guest favourite

Cottage in Swanton

4.93 out of 5 average rating, 28 reviews

Lakefront Cottage with Spectacular Views

Lakefront cottage with tremendous views and private dock . Home is on a quiet lane with pedestrian friendly activity. This is an original lakefront cottage that has been completely updated. Swim or fish from the dock or shoreline, bring your own boat, or use the two sea kayaks provided. Well equipped kitchen. Quaint, updated cabin offers relaxing atmosphere, serene family environment. No large groups or partiers allowed.