Vacation Rentals in Oakland, MD

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Oakland, MD

Book a vacation rental in Oakland that has the highest visitor rating. Here are 6 of the best vacation rentals in Oakland.
Lincoln Log Cabin
10

Excellent

·
Oakland
·
3 br
·
Sleeps 8
·
Kitchen · Fireplace · Outdoor Space ·
From
$383/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Fireplace
Garage Parking
Dishwasher
Wifi
Furnished
Ski In Ski Out
Oven
Assigned Parking
Other spaces
Kitchen
Price drop
An Apple Away
9.5

Excellent

·
Oakland
·
5 br
·
Sleeps 10
·
Fireplace · Outdoor Space · Dishwasher ·
From
$235/night
Check availability
Property
Apartment · 5 Beds · 2 baths
Amenities
Fireplace
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Ski In Ski Out
On Site Laundry
Other spaces
Kitchen, Balcony
Deep Creek Lake Townhome w/Deck & Water Views
9.3

Excellent

·
Oakland
·
2 br
·
Sleeps 6
·
Cable · Wifi · Toiletries ·
From
$126/night
Check availability
Property
Apartment · 2 Beds · 3 baths
Amenities
Cable
Wifi
Toiletries
Microwave
Lake
Dishwasher
Free Parking
Fireplace
Other spaces
Kitchen, Balcony
Home Sweet Cabin
9

Excellent

·
Oakland
·
4 br
·
Sleeps 10
·
Free Parking · Outdoor Space · Garage Parking ·
From
$290/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Free Parking
Garage Parking
Oven
Hot Tub
Fireplace
Assigned Parking
Furnished
Wifi
Other spaces
Kitchen
Cubs Den - Hot Tub- Walk to Lake- Fire Pit - Kayaks
8.8

Very good

·
Oakland
·
3 br
·
Sleeps 8
·
Air Conditioning · Outdoor Space · Oven ·
From
$294/night
Check availability
Property
Apartment · 3 Beds · 1 bath
Amenities
Air Conditioning
Oven
Dishwasher
Free Parking
Furnished
Fireplace
Wifi
Other spaces
Kitchen
Double Martini
8.5

Very good

·
Oakland
·
2 br
·
Sleeps 6
·
Garage Parking · Furnished · Ski In Ski Out ·
From
$346/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Garage Parking
Furnished
Ski In Ski Out
Assigned Parking
Oven
Wifi
Hot Tub
Fireplace
Other spaces
Kitchen

Our Recommended Vacation Rentals in Oakland, MD

We analyzed vacation rentals in Oakland from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Oakland to help you find a deal for your next trip.
Price drop
Birdhouse Lodge
7.6

Very good

·
Oakland
·
3 br
·
Sleeps 5
·
Oven · Furnished · Fireplace ·
From
$168/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Oven
Furnished
Fireplace
Air Conditioning
In Unit Laundry
Wifi
On Site Laundry
Ski In Ski Out
Other spaces
Kitchen
Price drop
Recreational Therapy

No rating

·
Oakland
·
2 br
·
Sleeps 5
·
Balcony · Wifi · Kitchen ·
From
$170/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Wifi
On Site Laundry
Hot Tub
Oven
Furnished
Fireplace
Other spaces
Balcony, Kitchen
Price drop
Leisure Lake

No rating

·
Oakland
·
5 br
·
Sleeps 12
·
Lake · Kitchen · Oven ·
From
$483/night
Check availability
Property
Apartment · 5 Beds · 3 baths
Amenities
Lake
Oven
Air Conditioning
Hot Tub
On Site Laundry
Furnished
Waterfront
Dishwasher
Other spaces
Kitchen, Workspace
Price drop
For All Seasons

No rating

·
Oakland
·
4 br
·
Sleeps 11
·
On Site Laundry · Hot Tub · Oven ·
From
$296/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
On Site Laundry
Hot Tub
Oven
Wifi
Air Conditioning
In Unit Laundry
Dishwasher
Fireplace
Other spaces
Kitchen

Budget-Friendly Vacation Rentals in Oakland, MD

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Oakland starting at $78. Use the price filter at the top of the page to search for more specific prices.
Swallow Falls Cabin #3
9.3

Excellent

·
Oakland
·
2 br
·
Sleeps 4
·
Kitchen · Air Conditioning · On Site Laundry ·
From
$78/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Air Conditioning
On Site Laundry
Oven
Fireplace
Furnished
Wifi
Other spaces
Kitchen
Nature's Escape
9.2

Excellent

·
Oakland
·
1 br
·
Sleeps 4
·
Air Conditioning · Wifi · Fireplace ·
From
$94/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Wifi
Fireplace
Ski In Ski Out
On Site Laundry
Furnished
Oven
Other spaces
Kitchen
Swallow Falls Cabin #2
8

Very good

·
Oakland
·
1 br
·
Sleeps 4
·
Wifi · Kitchen · On Site Laundry ·
From
$94/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Wifi
On Site Laundry
Ski In Ski Out
Air Conditioning
Oven
Furnished
Fireplace
Other spaces
Kitchen
High Mountain Villa

No rating

·
Oakland
·
3 br
·
Sleeps 8
·
Furnished · Mountains · Waterfront ·
From
$95/night
Check availability
Property
Hotel · 3 Beds · 2 baths
Amenities
Furnished
Mountains
Waterfront
Ski In Ski Out
Lake
Wifi
Oven
Hot Tub
Other spaces
Workspace, Kitchen
Location is everything! Near Wisp, Honi Honi Bar, and state park.
10

Excellent

·
Oakland
·
2 br
·
Sleeps 7
·
Air Conditioning · Furnished · Wifi ·
From
$95/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Air Conditioning
Furnished
Wifi
On Site Laundry
Other spaces
Kitchen
Bright condo with Deep Creek Lake views, wood fireplace & access to pool/hot tub
10

Excellent

·
Oakland
·
1 br
·
Sleeps 4
·
Waterfront · Oven · Furnished ·
From
$103/night
Check availability
Property
Condo · 1 Bed · 1 bath
Amenities
Waterfront
Oven
Furnished
Air Conditioning
Fitness Center
Fireplace
On Site Laundry
Dishwasher
Other spaces
Workspace, Balcony, Kitchen

Vacation Rentals With A Pool in Oakland, MD

Want to relax by the pool? Book one of these Oakland vacation rentals with a pool.
Price drop
Bears Lair

No rating

·
Oakland
·
4 br
·
Sleeps 8
·
Garage Parking · Assigned Parking · Ski In Ski Out ·
From
$448/night
Check availability
Property
Apartment · 4 Beds · 4 baths
Amenities
Garage Parking
Assigned Parking
Ski In Ski Out
Pool
Hot Tub
Fitness Center
Dishwasher
Fireplace
Other spaces
Kitchen
101B One Bedroom One Bath
10

Excellent

·
Oakland
·
1 br
·
Sleeps 4
·
Hot Tub · Air Conditioning · Oven ·
From
$269/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Hot Tub
Air Conditioning
Oven
Lake
Dishwasher
Pool
Free Parking
Furnished
Other spaces
Workspace, Balcony, Kitchen
Price drop
New! The Blue Footed Booby: Dogs Welcome, Lake Area!

No rating

·
Oakland
·
5 br
·
Sleeps 12
·
Furnished · Outdoor Space · Lake ·
From
$339/night
Check availability
Property
House · 5 Beds · 3 baths
Amenities
Furnished
Lake
Wifi
Waterfront
Oven
Fitness Center
Swimming Pool
Hot Tub
Other spaces
Balcony, Kitchen
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Updated: September 27, 2023