Holiday Rentals in Oakland
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Holiday Rentals in Oakland

New: Lakefront Luxury Home with Private Indoor Heated Pool!

Amazing Central Location! Lakefront! Hot tub/dock!

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

5BR lakefront retreat with hot tub, sauna, & dock

Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip

Lakefront, dog friendly, dock slip, hot tub, and fire pit

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

3-bed, charming modernized cottage tucked into wooded hillside in Deep Creek, MD

New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing

Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi

Dog-friendly secluded cabin with hot tub, firepit, lawn games, & great deck

Luxury Log Chalet w/ Pool & Fireplace

Cabin in the Woods

Charming Dog Friendly Cottage w/ Dock & Fire Pit

Dog-friendly townhouse with wood-burning fireplace, balcony & washer/dryer
Other types of properties in Oakland you may be interested in

Baja Motel
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.
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More accommodation in Oakland
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