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Holiday houses in Oakland

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Quick stats about holiday rentals in Oakland

  • Total holiday rentals

    Explore 10 holiday rentals in Oakland

  • Nightly prices starting at

    Oakland holiday rentals start at $102 NZD per night before taxes and fees

  • Verified guest reviews

    Over 880 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    10 of Oakland holiday rentals include Wi-Fi 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 holiday rentals in Oakland

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

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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, 167 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, 166 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, 218 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, 170 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, 116 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.
Holiday 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
Guest favourite
The exterior of the house features multiple levels, with a spacious deck accessible from the upper floor. Large windows are visible on the ground level, allowing natural light into the home. Surrounding greenery includes tall trees and well-maintained grass.
Home in McHenry

Cozy Lake House with Dock

Lazy Day Hideaway is a centrally located, family-friendly house with lake views. Lake access and a private dock slip are just a short walk from the deck. Enjoy a modern outdoor area with hot tub, cozy seating around the fire table, and dining area with grill. Indoors, find a spacious living area with wood burning fireplace, a fully stocked kitchen for all your cooking needs, and three comfortable bedrooms. Pet friendly (additional fees may apply). Disinfecting deep clean before every stay!

4.92 out of 5 average rating, 119 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, 113 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, 150 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!

4.97 out of 5 average rating, 119 reviews
Top Guest favourite
Home in Oakland

Lake View Loft Lodge on Deep Creek Lake

Seconds away from the lake, Trader's Coffee House, Brenda's Pizzeria, High Mountain Sports, and minutes away from Wisp Ski Resort, entertainment, shopping, food, and anything else you could want. Just eight miles south of Deep Creek Lake is historic Oakland, MD. Oakland is known for its small-town feel with local restaurants, small businesses, and popular festivals. Taking the time to visit Downtown Oakland is a must-see on your to-do list at Deep Creek Lake.

4.94 out of 5 average rating, 180 reviews
Guest favourite
A central living area features a modern design with an open floor plan. A combination of a cozy brown sofa and two armchairs surrounds a circular coffee table on a light rug. Large windows allow natural light to fill the space, highlighting the adjoining dining and kitchen area.
Home in McHenry

Deep Creek Gem: Hot Tub, Spa Bath & Game Room

Deep Creek house by the lake, modern with fast Wifi. You will get to enjoy a private hot tub, chef’s kitchen with wine fridge, reverse -osmosis water filter, spa-style bath with heated floors, and full game room - across from the lake with beautiful lake view, plus easy access to restaurants, bars and trails. 95+ 5-star reviews | Superhost since 2024 | sleep 8-10 Walk to boat and kayak rentals• 🔥 Hot tub • 🍳 Chef’s kitchen • 🛁 Spa bath • 🎲 Game room

4.96 out of 5 average rating, 104 reviews

Popular amenities for Oakland holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Oakland

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, 49 reviews
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, 58 reviews
Superhost
Home in Oakland

Private Lodge sleeps 31 guests Spectacular Views

4.91 out of 5 average rating, 54 reviews
Top Guest favourite
Home in Oakland

Deep Creek Dome Cabin | Fire Pit & EV Near Wisp

4.94 out of 5 average rating, 54 reviews
Guest favourite
Cabin in Oakland

Oakland Bear Lair | 7BR | Pool+Hot Tub + Game Room

4.91 out of 5 average rating, 23 reviews
Top Guest favourite
Cabin in Oakland

Cozy Cabin w/ Hot Tub/Game Room – near Deep Creek!

5.0 out of 5 average rating, 83 reviews
Superhost
Castle in Oakland

Mountaintop Castle @ Deep Creek Lake w/ Alpacas

4.67 out of 5 average rating, 6 reviews
Top Guest favourite
A modern kitchen features light-colored cabinetry and a large island with seating. Stainless steel appliances are complemented by an open layout. Natural light streams through the window, illuminating a well-organized counter space adorned with various kitchen essentials.
Home in Oakland

Broadford Park View

4.95 out of 5 average rating, 41 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