Oakland, Maryland Short-Term Rental Market
Oakland, MD short-term rentals near Deep Creek Lake averaged $594/night at 53.3% occupancy in June 2026.
Quick Answer: Oakland, Maryland is an active short-term rental market. average occupancy in the Deep Creek market area is 53%. average monthly revenue in the Deep Creek market area is $7,977. average daily rate in the Deep Creek market area is $594. the top operator in the Deep Creek market area is Railey Vacations with 590 listings. market score is 85/100 (grade B).
Market data reflects the Deep Creek regional market, which includes Oakland. Regulations, taxes, and permit details below are specific to Oakland.
Market Score Breakdown
Five dimensions StaySTRA evaluates per market.
Market Overview
Oakland is the county seat of Garrett County in far western Maryland’s Appalachian highlands, population 1,843, and serves as the service hub for Deep Creek Lake and Wisp Resort, Maryland’s only ski area. Garrett County draws an estimated 1.4 million visitors annually who spend roughly $315 million. In June 2026, the latest month with data, short-term rentals in this market averaged $594.44 per night at 53.3% occupancy, generating $7,977 in average monthly revenue per listing, among the highest revenue figures in this batch. Revenue rose 3.8% year over year and ADR climbed 5.3%, while occupancy was essentially flat (-0.3 point). By property type, apartments averaged $4,083/month, entire homes $8,032/month, and houses $8,655/month. Regionally, listing inventory skews heavily toward large homes: 5-bedroom-plus properties make up roughly 38% of the bedroom mix, and entire-place listings account for over 99% of inventory, reflecting the market’s large-group lake-house rental model.
Seasonal Patterns
| Month | Occupancy |
|---|---|
| Jan | 31% |
| Feb | 34% |
| Mar | 23% |
| Apr | 30% |
| May | 36% |
| Jun | 51% |
| Jul | 65% |
| Aug | 63% |
| Sep | 35% |
| Oct | 37% |
| Nov | 31% |
| Dec | 37% |
Month-by-month nightly rates and revenue figures for Oakland are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Top Short-Term Rental Operators in Deep Creek market area
Ranked by total active listings. Useful for understanding the competitive landscape. Operator data is published for the Deep Creek market as a whole, which includes Oakland, so these counts are not Oakland-only figures.
| # | Operator | Listings | Reviews | Rating |
|---|---|---|---|---|
| 1 | Railey Vacations | 590 | 9,424 | ★ 4.62 |
| 2 | Taylor-Made Deep Creek Vacations by Vtrips | 453 | 12,116 | ★ 4.50 |
| 3 | Vacasa | 97 | 6,082 | ★ 4.43 |
| 4 | Red Barn Vacations | 91 | 1,646 | ★ 4.80 |
| 5 | Prime Vacation Rentals | 44 | 959 | ★ 4.61 |
What Kind of STR Should I Buy in Oakland?
Revenue and nightly-rate breakdowns by bedroom count, property tier, and dwelling type for Oakland are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 16% |
| vrbo | 4.4% |
| both | 79.6% |
Home Value Trends (Oakland)
Typical home values, median sale prices, and the 10-year price trend for Oakland are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Insights
Booking-window and length-of-stay analysis for Oakland — how far ahead guests book and how to price around it — is available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Short-Term Rental Regulations
Short-term rentals are legal and well-established in Oakland and throughout Garrett County under the county’s Transient Vacation Rental Unit (TVRU) ordinance, in place since 2006 and administered by the Department of Planning & Land Management. A TVRU license is required to operate, and the county levies an 8% accommodations tax on rental receipts. A TVRU is a single-family dwelling rented for 14 days or less, capped at eight bedrooms with occupancy of two persons per bedroom plus four additional guests. There is no annual cap on rental nights and no owner-occupancy or primary-residence requirement. Licenses renew on a two-year cycle at roughly $250 total. Properties must meet safety standards including bedroom egress windows, one parking space per bedroom, bear-proof trash containers, and posted quiet hours from 10 pm to 8 am. Enforcement is rated moderate and largely complaint-driven, though the incorporated Town of Oakland maintains its own local zoning that can differ from county rules, so a property should be checked against both county TVRU requirements and town zoning before purchase.
Market Comparison
Oakland’s 53.3% occupancy in June 2026 sits close to the roughly 55% U.S. median often cited for short-term rentals, while its $594.44 ADR is nearly triple the roughly $220 national median, reflecting its position as a premium lake-resort market. No property manager snapshot data is currently published for this market, so a top-operator comparison is not available here; based on available data, ownership appears fragmented among individual lake-house owners rather than concentrated under a large professional manager.
Frequently Asked Questions About Oakland, Maryland
What is the average occupancy rate for Deep Creek Lake short-term rentals near Oakland, MD?
What is the average nightly rate for a short-term rental near Deep Creek Lake?
Do you need a permit to run a short-term rental near Oakland, MD?
How many bedrooms can a Deep Creek Lake short-term rental have?
When is the busiest season for short-term rentals near Deep Creek Lake?
What taxes apply to short-term rentals in Garrett County, MD?
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