Vacation Rentals in Oakland, MD
PRICE PER NIGHT
ACCOMMODATION TYPES
Peaceful Townhome
8.2
Very good
·
Oakland
·
2 br
·
Sleeps 8
·
Ceiling Fan · Toiletries · Walk In Closets ·
From
$110/nightProperty
Apartment · 2 Beds · 3 baths
Amenities
Ceiling Fan
Toiletries
Walk In Closets
Tv
Cable
Microwave
Free Parking
Dishwasher
Other spaces
Kitchen
Lake-view condo with deck & firepit - prime location
8.5
Very good
·
Oakland
·
2 br
·
Sleeps 6
·
On Site Laundry · Lake · Waterfront ·
From
$108/nightProperty
Condo · 2 Beds · 1 bath
Amenities
On Site Laundry
Lake
Waterfront
Air Conditioning
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Other spaces
Kitchen
8 Suites, Private Indoor Pool, Hot Tub, Lake Front with Private Dock!
6
Good
·
Oakland
·
8 br
·
Sleeps 16
·
Private Pool · Pool · In Unit Laundry ·
From
$1,452/nightProperty
House · 8 Beds · 10 baths
Amenities
Private Pool
Pool
In Unit Laundry
Lake
Waterfront
Hot Tub
Air Conditioning
Ski In Ski Out
Other spaces
Kitchen
AAH Chalet: Lakefront, Pool Table, Hot Tub, Fireplace, Private Dock!
9.3
Excellent
·
Oakland
·
5 br
·
Sleeps 12
·
Fitness Center · Mountains · In Unit Laundry ·
From
$259/nightProperty
House · 5 Beds · 3 baths
Amenities
Fitness Center
Mountains
In Unit Laundry
On Site Laundry
Lake
Waterfront
Hot Tub
Air Conditioning
Other spaces
Balcony, Kitchen
Birdhouse Lodge
9
Excellent
·
Oakland
·
3 br
·
Sleeps 5
·
Outdoor Space · In Unit Laundry · On Site Laundry ·
From
$121/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
In Unit Laundry
On Site Laundry
Air Conditioning
Ski In Ski Out
Fireplace
Furnished
Wifi
Oven
Other spaces
Kitchen
A Million Dollar View
8
Very good
·
Oakland
·
3 br
·
Sleeps 5
·
Outdoor Space · In Unit Laundry · On Site Laundry ·
From
$207/nightProperty
Apartment · 3 Beds · 4 baths
Amenities
In Unit Laundry
On Site Laundry
Lake
Waterfront
Air Conditioning
Dishwasher
Fireplace
Furnished
Other spaces
Balcony, Kitchen
Cubs Den - Hot Tub- Walk to Lake- Fire Pit - Kayaks
8
Very good
·
Oakland
·
3 br
·
Sleeps 8
·
Air Conditioning · Free Parking · Dishwasher ·
From
$248/nightProperty
Apartment · 3 Beds · 1 bath
Amenities
Air Conditioning
Free Parking
Dishwasher
Fireplace
Furnished
Wifi
Oven
Other spaces
Kitchen
Recreational Therapy
No reviews
·
Oakland
·
2 br
·
Sleeps 5
·
On Site Laundry · Balcony · Hot Tub ·
From
$108/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
On Site Laundry
Hot Tub
Fireplace
Furnished
Wifi
Oven
Other spaces
Balcony, Kitchen
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For All Seasons
No reviews
·
Oakland
·
4 br
·
Sleeps 11
·
Outdoor Space · In Unit Laundry · On Site Laundry ·
From
$134/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
In Unit Laundry
On Site Laundry
Hot Tub
Air Conditioning
Dishwasher
Fireplace
Furnished
Wifi
Other spaces
Kitchen
Double Martini
No reviews
·
Oakland
·
2 br
·
Sleeps 6
·
Hot Tub · Assigned Parking · Free Parking ·
From
$478/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Hot Tub
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Wifi
Other spaces
Kitchen
Dancing Bears Retreat
No reviews
·
Oakland
·
4 br
·
Sleeps 11
·
Hot Tub · Air Conditioning · Assigned Parking ·
From
$667/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Other spaces
Kitchen
Alla Famiglia
No reviews
·
Oakland
·
5 br
·
Sleeps 14
·
Mountains · Hot Tub · Air Conditioning ·
From
$694/nightProperty
Apartment · 5 Beds · 5 baths
Amenities
Mountains
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Other spaces
Kitchen
Clawson Cabin
No reviews
·
Oakland
·
3 br
·
Sleeps 6
·
Assigned Parking · Free Parking · Ski In Ski Out ·
From
$431/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Wifi
Oven
Other spaces
Kitchen
Lazy Bear Cove
No reviews
·
Oakland
·
4 br
·
Sleeps 12
·
Lake · Waterfront · Hot Tub ·
From
$727/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Lake
Waterfront
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Other spaces
Kitchen
Glencoe
No reviews
·
Oakland
·
5 br
·
Sleeps 12
·
Lake · Waterfront · Hot Tub ·
From
$1,169/nightProperty
Apartment · 5 Beds · 4 baths
Amenities
Lake
Waterfront
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Other spaces
Kitchen
Fernwood Retreat
No reviews
·
Oakland
·
4 br
·
Sleeps 12
·
Lake · Waterfront · Hot Tub ·
From
$906/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Lake
Waterfront
Hot Tub
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Other spaces
Kitchen
Camp Live Great
No reviews
·
Oakland
·
3 br
·
Sleeps 8
·
Balcony · Hot Tub · Air Conditioning ·
From
$444/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Other spaces
Balcony, Kitchen
Cedars on the Rocks
No reviews
·
Oakland
·
4 br
·
Sleeps 10
·
Lake · Waterfront · Hot Tub ·
From
$632/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Lake
Waterfront
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Other spaces
Kitchen
Better Lake Than Never
No reviews
·
Oakland
·
5 br
·
Sleeps 12
·
Hot Tub · Air Conditioning · Assigned Parking ·
From
$754/nightProperty
Apartment · 5 Beds · 6 baths
Amenities
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Other spaces
Kitchen
Blue Skies
No reviews
·
Oakland
·
5 br
·
Sleeps 14
·
Hot Tub · Air Conditioning · Assigned Parking ·
From
$816/nightProperty
Apartment · 5 Beds · 4 baths
Amenities
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Other spaces
Kitchen
A Skip-Away
No reviews
·
Oakland
·
3 br
·
Sleeps 8
·
Assigned Parking · Free Parking · Ski In Ski Out ·
From
$392/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Wifi
Oven
Other spaces
Kitchen
Lincoln Log Cabin
No reviews
·
Oakland
·
3 br
·
Sleeps 8
·
Assigned Parking · Free Parking · Ski In Ski Out ·
From
$363/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Wifi
Oven
Other spaces
Kitchen
Cabin Dreams
No reviews
·
Oakland
·
3 br
·
Sleeps 8
·
Lake · Waterfront · Hot Tub ·
From
$656/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Lake
Waterfront
Hot Tub
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Other spaces
Kitchen
Bee Tree II
No reviews
·
Oakland
·
4 br
·
Sleeps 10
·
Lake · Waterfront · Assigned Parking ·
From
$287/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Lake
Waterfront
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Other spaces
Kitchen
Arrowhead Village 02
No reviews
·
Oakland
·
3 br
·
Sleeps 8
·
Balcony · Lake · Waterfront ·
From
$469/nightProperty
Apartment · 3 Beds · 3 baths
Amenities
Lake
Waterfront
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Other spaces
Balcony, Kitchen
Skylodge
No reviews
·
Oakland
·
5 br
·
Sleeps 14
·
Hot Tub · Air Conditioning · Assigned Parking ·
From
$908/nightProperty
Apartment · 5 Beds · 4 baths
Amenities
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Other spaces
Kitchen
Serenity Chalet
No reviews
·
Oakland
·
3 br
·
Sleeps 8
·
Assigned Parking · Free Parking · Ski In Ski Out ·
From
$438/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Wifi
Oven
Other spaces
Kitchen
Runnin Down a Dream
No reviews
·
Oakland
·
3 br
·
Sleeps 7
·
Hot Tub · Air Conditioning · Assigned Parking ·
From
$463/nightProperty
Apartment · 3 Beds · 3 baths
Amenities
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Other spaces
Kitchen
On the Rocks
No reviews
·
Oakland
·
4 br
·
Sleeps 12
·
Hot Tub · Air Conditioning · Assigned Parking ·
From
$740/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Other spaces
Kitchen
Mystic Memories
No reviews
·
Oakland
·
5 br
·
Sleeps 11
·
Hot Tub · Air Conditioning · Assigned Parking ·
From
$813/nightProperty
Apartment · 5 Beds · 4 baths
Amenities
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Other spaces
Kitchen
Mountain Ridge Nest
No reviews
·
Oakland
·
1 br
·
Sleeps 6
·
Lake · Waterfront · Assigned Parking ·
From
$305/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Lake
Waterfront
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Other spaces
Kitchen
Meant to Be
No reviews
·
Oakland
·
3 br
·
Sleeps 8
·
Air Conditioning · Assigned Parking · Free Parking ·
From
$392/nightProperty
Apartment · 3 Beds · 3 baths
Amenities
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Wifi
Other spaces
Kitchen
Marlan Cove
No reviews
·
Oakland
·
3 br
·
Sleeps 8
·
Balcony · Lake · Waterfront ·
From
$482/nightProperty
Apartment · 3 Beds · 3 baths
Amenities
Lake
Waterfront
Hot Tub
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Other spaces
Balcony, Kitchen
Wright off the Lake
No reviews
·
Oakland
·
5 br
·
Sleeps 11
·
Hot Tub · Air Conditioning · Assigned Parking ·
From
$802/nightProperty
Apartment · 5 Beds · 4 baths
Amenities
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Other spaces
Kitchen
Views Brews
No reviews
·
Oakland
·
3 br
·
Sleeps 10
·
Lake · Waterfront · Assigned Parking ·
From
$395/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Lake
Waterfront
Assigned Parking
Free Parking
Ski In Ski Out
Furnished
Wifi
Oven
Other spaces
Kitchen
Wooded Bliss
No reviews
·
Oakland
·
4 br
·
Sleeps 10
·
Air Conditioning · Assigned Parking · Free Parking ·
From
$745/nightProperty
Apartment · 4 Beds · 2 baths
Amenities
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Fireplace
Furnished
Wifi
Oven
Other spaces
Kitchen
Whisked Away
No reviews
·
Oakland
·
5 br
·
Sleeps 14
·
Pool · Lake · Waterfront ·
From
$1,571/nightProperty
Apartment · 5 Beds · 5 baths
Amenities
Pool
Lake
Waterfront
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Other spaces
Kitchen
Viva Vista
No reviews
·
Oakland
·
6 br
·
Sleeps 16
·
Lake · Waterfront · Hot Tub ·
From
$1,341/nightProperty
Apartment · 6 Beds · 4 baths
Amenities
Lake
Waterfront
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Other spaces
Kitchen
Valhalla
No reviews
·
Oakland
·
5 br
·
Sleeps 14
·
Lake · Waterfront · Hot Tub ·
From
$1,266/nightProperty
Apartment · 5 Beds · 3 baths
Amenities
Lake
Waterfront
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Other spaces
Kitchen
Unreel
No reviews
·
Oakland
·
5 br
·
Sleeps 13
·
Lake · Waterfront · Hot Tub ·
From
$882/nightProperty
Apartment · 5 Beds · 3 baths
Amenities
Lake
Waterfront
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Other spaces
Kitchen
Up a Creek
No reviews
·
Oakland
·
4 br
·
Sleeps 10
·
Pool · Lake · Waterfront ·
From
$889/nightProperty
Apartment · 4 Beds · 4 baths
Amenities
Pool
Lake
Waterfront
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Other spaces
Kitchen
Under the Stars
No reviews
·
Oakland
·
9 br
·
Sleeps 26
·
Private Pool · Pool · Lake ·
From
$2,621/nightProperty
Apartment · 9 Beds · 8 baths
Amenities
Private Pool
Pool
Lake
Waterfront
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Other spaces
Kitchen
Loch Nest
No reviews
·
Oakland
·
5 br
·
Sleeps 14
·
Lake · Waterfront · Hot Tub ·
From
$1,122/nightProperty
Apartment · 5 Beds · 5 baths
Amenities
Lake
Waterfront
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Fireplace
Other spaces
Kitchen
VVS - Very Very Special
No reviews
·
Oakland
·
8 br
·
Sleeps 20
·
Balcony · Lake · Waterfront ·
From
$2,619/nightProperty
Apartment · 8 Beds · 7 baths
Amenities
Lake
Waterfront
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Other spaces
Balcony, Kitchen
Sunset Pointe
No reviews
·
Oakland
·
6 br
·
Sleeps 16
·
Lake · Waterfront · Hot Tub ·
From
$1,460/nightProperty
Apartment · 6 Beds · 5 baths
Amenities
Lake
Waterfront
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Other spaces
Kitchen
Bear Paws
No reviews
·
Oakland
·
2 br
·
Sleeps 8
·
Hot Tub · Assigned Parking · Free Parking ·
From
$465/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Hot Tub
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Wifi
Other spaces
Kitchen
Knotty Pines
No reviews
·
Oakland
·
3 br
·
Sleeps 10
·
Hot Tub · Air Conditioning · Assigned Parking ·
From
$536/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Other spaces
Kitchen
Bearadise
No reviews
·
Oakland
·
3 br
·
Sleeps 12
·
Pool · Hot Tub · Air Conditioning ·
From
$492/nightProperty
Apartment · 3 Beds · 3 baths
Amenities
Pool
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Other spaces
Kitchen
Kare Bear Cabin
No reviews
·
Oakland
·
3 br
·
Sleeps 8
·
Air Conditioning · Assigned Parking · Free Parking ·
From
$449/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Wifi
Other spaces
Kitchen
Whispering Pines
No reviews
·
Oakland
·
5 br
·
Sleeps 10
·
Balcony · Hot Tub · Air Conditioning ·
From
$744/nightProperty
Apartment · 5 Beds · 5 baths
Amenities
Hot Tub
Air Conditioning
Assigned Parking
Free Parking
Ski In Ski Out
Dishwasher
Fireplace
Furnished
Other spaces
Balcony, Kitchen
Showing 1 - 50 of 398 results
Updated: March 26, 2023
Learn about vacation rentals in
Oakland
Explore 398 vacation rentals near Oakland, Maryland. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Oakland, you can see photos of Oakland vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Oakland vacation rentals in specific areas. Whether you’re looking for a Oakland staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Oakland is $108 per night and the highest price is $2,621 per night.
12 of the vacation rentals near Oakland are
apartments or condos. The average bathroom count for this property type is 2. The median price for these vacation
units is $109 per night. There are
currently 3 vacation units under this
price. 363 of the vacation rentals near Oakland are houses.
The average bathroom count for a vacation house near Oakland is
3. The average price for vacation houses near Oakland is $737 per night. There are 301 vacation homes under this price. The most common
amenities for vacation rentals near Oakland are: furnished, wifi, and oven. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
13 available
2 bed rentals
33 available
3 bed rentals
97 available
4+ bed rentals
255 available
Getting around Oakland
Walking
6/10
Grab your reusable bags–many shops and stores are within walking distance.
Car
8/10
This area is close to freeways and has adequate parking options.
Cycling
4/10
This is semi-bikeable, but you’ll need another way of getting around.
Transit
5/10
Frequent public transit options are within walking distance.
Points of interest in Oakland
Groceries
7/10
At least one grocery store within a 15-minute walk
Shopping
5/10
Variety of shops within walking distance
Cafes
5/10
Some cafés within walking distance
Restaurants
6/10
Variety of restaurants within walking distance
Parks
8/10
Large amount of park space nearby
Nightlife
3/10
Few or no bars within walking distance
Vacation Rentals in Oakland, MD FAQ
How many vacation rentals in Oakland are available?
There are currently 398 vacation rentals in Oakland available. Our vacation rentals in Oakland include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Oakland?
Yes, right now there are 116 pet friendly vacation rentals in Oakland. A pet friendly vacation rental in Oakland means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Oakland with a pool?
Yes there are vacation rentals with a pool available in Oakland, MD. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Oakland with internet access?
As of March 26, 2023, there are vacation rentals with internet access available in Oakland, Maryland. Check out more enjoyable destinations on Vacations by Zumper.
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