Holiday Rentals in Oakland
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Check rental availability in Oakland
Holiday Rentals in Oakland

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Dog-friendly house on the lake, central AC, & EV charger

Lakefront/Dock/Amazing views HotTub

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Sisters Treehouse

AMAZING LAKE FRONT 7 BR Home, Hot Tub, Fire Pit, Dock, Pool Table

Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip

The winter is coming !!!

EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

Charming Dog Friendly Cottage w/ Dock & Fire Pit

Dog-friendly townhouse with wood-burning fireplace, balcony & washer/dryer

Beautiful Lakeside Cottage on Quiet Street with Private Dock, Kayaks & Fire Pit

Level lakefront, family-friendly, hot tub, low fees, private dock

West Oak: New home, 3 suites, hot tub, boat slip, outdoor fireplace
Other types of properties in Oakland you may be interested in

The Garrett Inn
Holiday Accommodation Oakland
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Oakland are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Oakland itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Oakland holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Oakland, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Oakland with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
More Destinations
- Caravan Parks in Accident
- Accident Hotels
- Altamont Hotels
- Barton Hotels
- Blakeslee Hotels
- Pet Friendly Hotels in Cumberland
- Cumberland Hotels
- Hotels near Deep Creek Lake
- Hotels near Deep Creek Lake State Park
- Deer Park Hotels
- Hotels near Downtown Cumberland Historic District
- Eckhart Mines Hotels
- Frostburg Hotels
- Little Orleans Hotels
- Loch Lynn Heights Hotels
- Luke Hotels
- Mccoole Hotels
- Mchenry Hotels
- Lodges in Mount Savage
- Hotels near Noah's Ark
- Cottages in Oakland
- Oakland Hotels
- Ocean Hotels
- Penelacres Hotels
- Rawlings Hotels
- Hotels near Savage River
- Silver Ridge Hotels
- Swanton Hotels
- Hotels near Thousand Acres Lakeside Golf Course
- Westernport Hotels
^Eligibility requirements and conditions apply










