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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 $104 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 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
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
5.0 out of 5 average rating, 111 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.

ValueLocationCondition

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
4.98 out of 5 average rating, 170 reviews

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).

ValueFamilySleep quality

Guest favourite
Cabin in McHenry
4.96 out of 5 average rating, 167 reviews

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! 

ValueLocationCleanliness

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
4.99 out of 5 average rating, 220 reviews

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.

ValueFamilyDecor

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
4.95 out of 5 average rating, 172 reviews

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.

LocationFamilyOutdoor spaces

Top Guest favourite
Cabin in Oakland
5.0 out of 5 average rating, 118 reviews

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!

LocationValueLong stay

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
4.97 out of 5 average rating, 145 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.

FamilyLocationLaundry

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
5.0 out of 5 average rating, 114 reviews

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

LocationFamilyWalkability

Guest favourite
Treehouse in McHenry
4.95 out of 5 average rating, 153 reviews

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.

LocationValueCheck-in

Top Guest favourite
Cabin in Oakland
4.98 out of 5 average rating, 121 reviews

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!

LocationFamilyPets

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
4.95 out of 5 average rating, 106 reviews

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

FamilyValueOutdoor spaces

Top Guest favourite
The Grist Mill is showcased with its rustic wooden exterior complemented by a stone foundation. A charming red water wheel and a small pond are seen in the foreground, surrounded by neatly arranged landscaping and a clear blue sky above.
Tiny home in Oakland
5.0 out of 5 average rating, 192 reviews

The Grist Mill

The Grist Mill is a peaceful, one-of-a-kind tiny cabin near Oakland, MD, built to resemble an old-fashioned grist mill with a working water wheel. Guests love the sunsets, cleanliness, and thoughtful extras. Highlights: Peaceful rural setting ~10 min to Oakland ~20 min to Deep Creek Lake & Wisp Near Swallow Falls, Blackwater Falls, Davis & Thomas 500+ Mbps Wi-Fi Snacks, drinks & bottled water Seasonal fire pit Private entrance & self check-in

LocationValueWi-Fi

Popular amenities for Oakland holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Oakland

Guest favourite
Cabin in Oakland
4.92 out of 5 average rating, 271 reviews

Lakehound Lodge - lake view, pet friendly

LocationFamilyParking

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
5.0 out of 5 average rating, 60 reviews

The Barn @ Silo Farm | Deep Creek Lake, MD

FamilyLocationAccess

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

Deep Creek Dome Cabin | Fire Pit & EV Near Wisp

LocationFamilySkiing

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
4.98 out of 5 average rating, 50 reviews

Speakeasy | Bunk Room | Hot Tub | Private 2 acres

FamilyLocationBarbecue

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

Brand NEW, Lake Access, Dog Friendly, Hot Tub

HospitalityAccessCondition

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

Private Lodge sleeps 31 guests Spectacular Views

FamilyValueCheckout

Guest favourite
Cabin in Oakland
4.92 out of 5 average rating, 25 reviews

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

FamilyValueDecor

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
4.9 out of 5 average rating, 72 reviews

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

LocationValueParking

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