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 $83 AUD 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.
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!
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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.
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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).
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LakeAccess 4BR DeckSlide OD Movies HotTub Kayaks
Our redesigned 4 bedroom cabin with modern finishes & amenities creates amazing family experiences: - Wisp - 8 Min, 4.1 Miles Away - Deck Slide & Swings - 2x 100" Outdoor Movie Screen & Bluetooth Projector - 7 Person Hot Tub - Fire Pit w/ Comfortable Seating - Playstation4, Pac-Man, Shuffleboard - Well-Equipped Kitchen, Propane Grill - 350ft to Lake/Beach/Swimming - 1 Person & 2 Person Kayaks & Paddleboard - Roku HDTVs - All Rooms - Pro Wifi System - 600+Mbps Great for Remote Work - EV Charger
FamilyValueOutdoor spaces
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.
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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!
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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.
FamilyValueSkiing
Honeymoon Spa Experience! Pond! Sauna! Hot Tub!
High End, Romantic Escape with Private Pond nestled in the pines, located 1 mile from Deep Creek Lake State Park, Custom Sauna, Hot Tub, Outdoor TV, Cozy Rocking Chairs, Propane Fire Pit, Soaking Tub, Robes, Plush King Bed, Espresso Machine, Margaretaville Margarita Machine, Firepit by the pond, Sound Appealing? Then this is the place for you! Re-connect with your signifiant other in a spa like, mountain setting. We provide all the essentials and much more! Just 15 minutes from Wisp Resort.
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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
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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.
ValueFamilyGetting around
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!
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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
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Popular amenities for Oakland holiday rentals
Other great holiday rentals in Oakland
Lake View Loft Lodge on Deep Creek Lake
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Incredible Cozy Cabin Immersed in Nature
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Stone Haven
ValueLocationCheckout
The Barn @ Silo Farm | Deep Creek Lake, MD
LocationFamilyBiking
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
FamilyLocationSleep quality
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
FamilyLocationSkiing
Private Lodge sleeps 31 guests Spectacular Views
LocationFamilyHot tub
Oakland Bear Lair|7BR Luxury Log|Pool, Hot tub
FamilyLocationIndoor spaces
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
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- Fallingwater
- Seven Springs Mountain Resort
- Wisp Resort
- Timberline Mountain
- Ohiopyle State Park
- Blackwater Falls State Park
- Tygart Lake
- Canaan Valley Resort & Conference Center
- Rock Gap State Park
- Canaan Valley Ski Resort
- White Grass
- Swallow Falls State Park
- Deep Creek Lake State Park
- Laurel Hill State Park
- Coopers Rock State Forest
- Fort Necessity National Battlefield
- Audra State Park
- Lodestone Golf Course
- Smoke Hole Caverns
- Western Maryland Scenic Railroad