Compare Vacation Rentals & Rent By Owner Homes in Oakland, Maryland, USA
About Oakland Vacation Rentals
With more than 1024 Oakland vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Oakland.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Oakland, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Oakland. Places to stay near Oakland are 1674.41 ft² on average, with prices averaging US $452 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Oakland with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in Oakland, MD
Oakland Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Oakland?
- Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
- The Love Shack- The BEST Couples and Small Family Retreat at Deep Creek Lake!
- Sunny Escape 2 - A new era for a familiar lake front home
- 5 STAR OWNER Managed, Lake Xcess, dock, Pool, Pickle-ball, Home Theater, firepit
- Level lakefront, family-friendly, hot tub, low fees, private dock
- Timroc II, FIVE STAR REVIEWS! LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!
- Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swingn
- Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip
- Fall Fun at our Centrally Located Lake View Condo that sleeps 6!
- Unobstructed lake views from living areas. Restaurants & activities in minutes
How many Rentbyowner vacation rentals are available in Oakland?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 1024 in the Oakland area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Oakland.
Nearby Neighborhood (6)
| Neighborhood | Property Count |
|---|---|
| Mountainside Vacation Rentals in Cumberland, Maryland | 75 |
| Blakeslee Vacation Rentals in Cumberland, Maryland | 53 |
| Paradise Point Vacation Rentals in Cumberland, Maryland | 33 |
| Silver Ridge Vacation Rentals in Cumberland, Maryland | 1453 |
| The View Vacation Rentals in Cumberland, Maryland | 1734 |
| Timbers on the Yough Vacation Rentals in Cumberland, Maryland | 104 |
