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Vacation rentals in Oakland

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Quick stats about vacation rentals in Oakland

  • Total vacation rentals

    Explore 10 vacation rentals in Oakland

  • Nightly prices starting at

    Oakland vacation rentals start at $84 CAD per night before taxes and fees

  • Verified guest reviews

    Over 880 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Wifi availability

    10 of Oakland vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Oakland rentals

  • 4.8 Average rating

    Oakland stays are highly rated by guests—averaging 4.8 out of 5!

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
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.

5.0 out of 5 average rating, 111 reviews
Top guest favourite
A spacious outdoor hot tub is positioned on a patio, featuring soft blue lighting and a clear water surface. It is surrounded by green grass and trees in the background.
Home in Oakland

Mountain Air Oasis with Hot Tub

Relax with the whole family or friends at this peaceful private 2 acre property, close to Maryland's natural attractions! A family-friendly three bedroom home 1,380 sq. ft secluded in a rural neighborhood. Wildlife to watch and enjoy! Relax with a campfire or soak in the hot tub! We are located approximately 30 minutes from Swallow Falls State Park, Deep Creek Lake, and Black Water Falls State Park. We are also within 10 minutes of two wedding venues (The White Barn, and Twin Tales Event Farm).

4.98 out of 5 average rating, 170 reviews
Guest favourite
Cabin in McHenry

Mad Men Lake House*LAKEFRONT*Fam&Dog Friendly*OUTD

Welcome to the BEST Deep Creek experience. Unwind on our decks as you watch water lap up on the shore with a refreshing drink in hand. Relax those muscles in our hot tub, gazing at the winter sky above after an invigorating day on the slopes! Take in the mountain breeze as you roast smores around our fire pit! Fish/swim off our shared dock. Witness spectacular sunrises as you take an early morning paddle w/ our kayaks & canoe. Plus, we offer an OUTDOOR MOVIE EXPERIENCE for the best vacay EVER! 

4.96 out of 5 average rating, 167 reviews
Top guest favourite
The treehouse is elevated among bare branches, featuring a large deck with seating. Warm lighting highlights the wooden exterior, and expansive windows provide views of the surrounding forest. Steps lead down to the ground, enhancing accessibility to the natural setting.
Treehouse in McHenry

Bird's Eye View

Nestled high amidst the sturdy branches, "Bird's Eye View" is a sanctuary suspended between earth and sky. Located less than 5 minutes from Deep Creek Lake and perched among the foliage, our treehouse offers a panoramic perspective of the surrounding forest, granting its visitors an unparalleled vantage point to observe nature's wonders. Relax in the hot tub and take in an amazing sunset. The home is a harmonious blend of locally-crafted art and furniture to add rustic charm and modern comfort.

4.99 out of 5 average rating, 221 reviews
Guest favourite
The exterior showcases a charming chalet surrounded by trees, featuring a spacious wrap-around deck with patio seating and a fire pit area. The large windows reflect the warm indoor lights, revealing an inviting atmosphere that complements the natural surroundings.
Chalet in Swanton

Ella Bella Chalet: Hot Tub, Stunning Views, Wi-Fi

Welcome to Ella Bella Chalet! Escape to our modern, yet cozy cabin boasting panoramic breathtaking views and an array of upscale amenities. Relax in the hot tub under starlit skies or gather around the fire pit for cozy evenings. Located near Wisp Ski Resort, golf courses, and endless lake activities, including boating, fishing, tubing and kayaking. Explore nearby hiking trails and attractions like Swallow Falls State Park, Adventure Sports Center International, zip lining, biking, and more.

4.95 out of 5 average rating, 173 reviews
Top guest favourite
Cabin in Oakland

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

Escape to our charming Spruce 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!

5.0 out of 5 average rating, 118 reviews
Top guest favourite
The exterior of a wooden cabin is framed by tall trees, with warm light glowing from the large front windows. A spacious deck is visible at the entrance, surrounded by lush greenery and natural stone pathways leading through the forest.
Vacation home in Oakland

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.

4.97 out of 5 average rating, 145 reviews
Top guest favourite
Home in Oakland

Deep Creek Dome Cabin | Fire Pit & EV Near Wisp

Nestled near Deep Creek Lake, Wisp Resort, and Swallow Falls State Park, Creekside Quest is a family-friendly, all-season getaway offering the perfect blend of comfort, style, and adventure in Oakland, Maryland. Enjoy the private outdoor dome theater for movie nights under the stars, an EV charger, inviting bar area, fire pit, and full game room for hours of fun. With a fully stocked kitchen, coffee bar, and modern design, this luxurious retreat is ideal for families, couples, and friends.

4.95 out of 5 average rating, 58 reviews
Top guest favourite
The cabin's exterior showcases a classic mountain design with a green metal roof and inviting porch. Large windows are framed by wooden beams, and blooming flowers add a splash of color to the landscape. A grassy area surrounds the cabin, enhancing the serene atmosphere.
Cabin in Oakland

CharmingHome7PersonHotTubFirePit2Arcades9MintoWisp

Spacious and secluded, 9 mins from Wisp Resort! -Updated cabin in woods, hot tub, 12 ft shuffle board, arcade games, darts, fire-pit! -Sleeps 16 with four bedrooms, two pull out sofa beds, futon, and daybed with trundle -7 person hot tub with 49 jets and waterfall -Large outdoor seating area around a custom fire pit -Two full length decks on front and back of the cabin -Peak-a-boo lake-view -Full kitchen and outdoor grill -High speed wifi -Community Aquatic Recreation Center access

5.0 out of 5 average rating, 114 reviews
Guest favourite
Treehouse in McHenry

Treehouse in Deep Creek Lake

Newly built, Whispering Woods is a custom-made treehouse surrounded by stunning scenery just minutes from Deep Creek Lake and Wisp Resort. No detail was overlooked in the spacious interior that includes 2 bedrooms, 2 baths, a fully equipped kitchen, and a sitting area with a 65” TV. The amazing outdoor living space includes expansive decks, a fire pit, and a bubbling hot tub. For a unique and memorable experience from start to finish, come relax and reconnect at this treetop escape.

4.95 out of 5 average rating, 154 reviews
Top guest favourite
Cabin in Oakland

Captain's Quarters Deep Creek Log Cabin Oasis

Welcome to our slice of peace and relaxation in beautiful Deep Creek! Spacious and serene log cabin. The Captains Quarters is the perfect getaway. 2BDRM, propane fireplace (Nov-Apr), full kitchen, and a 6+ person hot tub. Dogs welcome but please let us know and pay the fee. 2 comfy Queen mattresses, towels and linens provided, hi speed internet, smart TV’s, and Bluetooth soundbar. Relax in our two heated massage chairs in the family room. We want to earn a 5 star review!

4.98 out of 5 average rating, 122 reviews
Top guest favourite
The cabin exterior showcases a blend of rustic wooden siding and modern architectural design. Warm lights illuminate large windows, highlighting the inviting entrance. Surrounding trees provide a natural backdrop, and a large stone is visible in the foreground, enhancing the private woodland setting.
Cabin in Accident

Rustic Luxe Cabin (4x4 Required)

Situated on 10 acres and surrounded by a 600-acre nature conservancy, Rustic Lux is a new construction that fuses the charming details of a rustic cabin with high-end modern luxury. Guests can enjoy complete privacy with quick access to all the wonders of Deep Creek Lake! Rustic Lux is only 4 miles from the lake and Wisp Ski Resort. The road back to the cabin is a little rough but is pretty flat and in no way dangerous. We recommend 4 wheel drive vehicles.

4.98 out of 5 average rating, 98 reviews

Popular amenities for Oakland vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Oakland

Top guest favourite
The exterior of a large wooden barn structure is presented, featuring multiple windows and two prominent cupolas. A spacious deck is visible at one end, along with a seating area, all set against a natural landscape.
Home in Oakland

The Barn @ Silo Farm | Deep Creek Lake, MD

5.0 out of 5 average rating, 60 reviews
Top guest favourite
A spacious living room features a wood-burning fireplace set in a stone surround, complemented by two cozy armchairs. A dark leather sectional encircles a round coffee table on a patterned rug. Large windows let in natural light, with wooden walls enhancing the cabin's charm.
Cabin in Oakland

Speakeasy | Bunk Room | Hot Tub | Private 2 acres

4.98 out of 5 average rating, 50 reviews
Guest favourite
Home in Oakland

Private Lodge sleeps 31 guests Spectacular Views

4.91 out of 5 average rating, 57 reviews
Guest favourite
Home in Oakland

Brand NEW, Lake Access, Dog Friendly, Hot Tub

5.0 out of 5 average rating, 5 reviews
Guest favourite
Cabin in Oakland

Secluded Mtn Cabin: 7BR, Pool, Hot Tub, Game Room

4.92 out of 5 average rating, 25 reviews
Top guest favourite
A spacious living area features a spiral staircase leading to the upper level. Wood paneling adorns the walls, complemented by a stone fireplace and large windows allowing natural light. Comfortable seating options include a blue chair, a green sofa, and a cozy couch, fostering a relaxed atmosphere.
Cabin in Oakland

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

4.97 out of 5 average rating, 34 reviews
Guest favourite
An expansive open-concept living area showcases a cozy seating arrangement with a brown leather sofa and a light grey couch. Large windows offer views of the surrounding trees and lake. A modern kitchen with a countertop bar is visible, accompanied by pendant lighting.
Cabin in Oakland

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

4.9 out of 5 average rating, 73 reviews
Superhost
Castle in Oakland

Mountaintop Castle @ Deep Creek Lake w/ Alpacas

4.71 out of 5 average rating, 7 reviews

Frequently Asked Questions

  • What are the best places to stay in Oakland?

    Stays around deep water lakes or forested areas are often recommended for nature access, while accommodations near the historic downtown area offer walkable options to shops and restaurants. Cabins, cottages, and homes with mountain views are also popular.

  • What are the best things to do in Oakland with kids?

    Kids enjoy swimming or paddleboarding at Deep Creek Lake State Park, easy hikes to waterfalls, and stopovers at interactive museums. In winter, sledding and snow play are frequently suggested.

  • What are some of the best things to do in Oakland?

    Explore outdoor trails at Swallow Falls State Park, visit local art galleries or history museums, and enjoy boating or fishing on Deep Creek Lake. Seasonal festivals and markets highlight local culture and crafts.

  • How is the weather in Oakland?

    Oakland experiences cold, snowy winters with average temperatures ranging from 18 to 38°F (-8 to 3°C), and cool, pleasant summers around 56 to 74°F (14 to 23°C). Rain is spread throughout the year, with spring and summer being the wettest seasons.

  • When is the best time to visit Oakland?

    Late spring through early fall is often recommended for Oakland, when temperatures typically range from 46 to 74°F (8 to 23°C), and outdoor activities are widely available. Colorful leaves in autumn and winter snows also attract visitors seeking seasonal scenery.

  • What are the best places to visit in Oakland?

    Popular places to explore in Oakland include Deep Creek Lake State Park, the historic Oakland Train Station, and Swallow Falls State Park. Visitors frequently suggest local museums and scenic parks around the town.

  • What are some hiking trails in Oakland?

    Hikers can explore the Swallow Falls Canyon Trail, forest paths in Deep Creek Lake State Park, or gentle routes in Herrington Manor State Park. Local trails often highlight mountain scenery and waterfalls.

  • What are some family activities we can do in Oakland?

    Families enjoy picnicking and swimming at Deep Creek Lake State Park, hiking waterfall trails, or visiting the Garrett County Historical Museum. In winter, snow activities like sledding and ice fishing are common.

  • What are some of the best day trip ideas from Oakland?

    Consider exploring additional state parks, small mountain towns, or local caves around Oakland. Winery tours, historic sites, and scenic drives also provide a change of pace from the town center.

  • Are there any pet friendly accommodations available in Oakland?

    Many stays in Oakland welcome pets, especially cabins and homes near lakes, parks, or woodland areas. Paths and trails in nearby parks provide space to explore with dogs.

  • What are some local tips for visiting Oakland?

    Early mornings around the mountain lakes tend to be quieter, and dressing in layers helps with shifting temperatures. Check local calendars for pop-up events, and bring cash for small shops or markets.

  • What is Oakland known for?

    Oakland is known for its scenic mountain setting, historic downtown, and easy access to recreational lakes, waterfalls, and state parks. Seasonal events, local farms, and a tradition of outdoor adventure also define the area.

  • What are the best hidden gems to explore in Oakland?

    Hidden gems in Oakland often include small art galleries, heritage museums, or less-trafficked waterfall trails in nearby parks. Local antique shops and community events showcase the area's distinct culture.

  • What are the best foods to try in Oakland?

    Oakland has Appalachian-inspired dishes, farm-fresh produce, and baked goods such as fruit pies. Locally raised meats, traditional comfort foods, and maple syrup treats are frequently suggested.

  • What should I bring for a trip to Oakland?

    Pack layers, as temperatures can vary, along with outdoor essentials like sturdy walking shoes, rain jackets, and sun protection. In colder months, warm jackets, hats, and gloves are helpful for snowy conditions.

  • What is the nightlife in Oakland like?

    Oakland has a relaxed nightlife, with gathering spots for live music, local brews, or casual dining. Occasional performances, open mic nights, and community events keep evenings welcoming.

  • What are the most popular events or festivals in Oakland?

    Oakland frequently hosts events like an autumn foliage festival, local craft fairs, and seasonal farmers' markets. Holiday parades and community gatherings also bring people together throughout the year.

  • Are there family friendly vacation rentals in Oakland?

    Oakland has vacation rentals frequently suggested for families, including homes near lakes, cabins around forested areas, and places with spacious living areas or outdoor spaces. Many feature access to nature trails or recreational amenities.

Destinations to explore