What types of vacation rentals are available in Oakland?

There are loads of different property types that you can make your vacation home in Oakland. You’ll find apartments, cabins, condos, houses and lodges.

What are some of the most-loved vacation rentals available in Oakland?

If you’re looking for something special, the vacation rental most loved by KAYAK users is Haley Farm Bed & Breakfast.

Are there any pet-friendly vacation rentals in Oakland?

There are a number of dog and pet-friendly Oakland vacation rentals, with around 16% allowing you to bring your pet along with you.

How much is a vacation rental in Oakland for tonight?

In the last 72 hours, users have found Oakland vacation rentals for tonight for as low as $228.

How much is a vacation rental in Oakland for this weekend?

In the last 72 hours, users have found Oakland vacation rentals for this weekend for as low as $216 per night.

How can I find vacation rentals near me in Oakland?

Take a look at our vacation rentals map to find the best vacation rental homes near you.

Oakland Vacation Rentals from $36/night

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Best Oakland vacation rentals

Oakland, MD

Pet friendly

Oakland, MD

Parking

Free Wi-Fi

Oakland, MD

Parking

Free Wi-Fi

$271+

Check availability

Deep Creek Lake Townhome with Deck and Water Views

Oakland, MD

9.4Wonderful(19)

Free Wi-Fi

$274+

Check availability

Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village

Oakland, MD

Pet friendly

Spa

Oakland, MD

Oakland, MD

Parking

Free Wi-Fi

Pet friendly

$329+

Check availability

Lake View

Oakland, MD

Parking

Free Wi-Fi

Pet friendly

$502+

Check availability

Just About Paradise 5 Bedroom House

Oakland, MD

8.6Very good(10)

Free Wi-Fi

Pet friendly

Spa

$533+

Check availability

Serene Mountain Escape: Hot Tub, Foosball, Views

Oakland, MD

Spa

$488+

Check availability

306C One Bedroom One Bath

Oakland, MD

9.9Wonderful(6)

Parking

Free Wi-Fi

Pool

Spa

$237+

Check availability

Serenity Ridge

Oakland, MD

Free Wi-Fi

Spa

Oakland, MD

Chalet with lake views & dock right across the street!

Oakland, MD

$790+

Check availability

Schmidt Lodge 3 Bedroom House

Oakland, MD

Free Wi-Fi

Spa

Oakland, MD

Low season	November
High season	May
Average price (weeknight)	$291
Average price (weekend night)	$211

Cheapest month to stay with an average 28% drop in price.

Most expensive month to stay with an average 51% rise in price.

Average Sun - Thu price over the last 2 weeks.

Average Fri & Sat price over the last 2 weeks.

Hot tub is the most popular vacation rental property amenity in Oakland
The best vacation rental properties in Oakland are Timroc II, Five Star Reviews! Lake Access, Great Swimming, Private 2 Acres! (10.0, 20 reviews), The Love Shack-- The Best Couples And Small Family Retreat At Deep Creek Lake! (9.8, 112), and Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village (9.8, 52), based on ratings and reviews from real travelers.
If you’re looking for a cheap vacation rental in Oakland, you should consider visiting during the low season. The cheapest vacation homes in Oakland can be found in November and February.
The cheapest night for renting a vacation home in Oakland is Saturday. In contrast, the most expensive is Sunday.
Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Oakland for 3 days.
The cheapest Oakland vacation rental found on KAYAK in the last 2 weeks was $350, while the most expensive was $436.

See more tips

What types of vacation rentals are available in Oakland?
There are loads of different property types that you can make your vacation home in Oakland. You’ll find apartments, cabins, condos, houses and lodges.
What are some of the most-loved vacation rentals available in Oakland?
If you’re looking for something special, the vacation rental most loved by KAYAK users is Haley Farm Bed & Breakfast.
Are there any pet-friendly vacation rentals in Oakland?
There are a number of dog and pet-friendly Oakland vacation rentals, with around 16% allowing you to bring your pet along with you.
How much is a vacation rental in Oakland for tonight?
In the last 72 hours, users have found Oakland vacation rentals for tonight for as low as $228. Search here for similar prices
How much is a vacation rental in Oakland for this weekend?
In the last 72 hours, users have found Oakland vacation rentals for this weekend for as low as $216 per night. Search here for similar prices
How can I find vacation rentals near me in Oakland?
Take a look at our vacation rentals map to find the best vacation rental homes near you.