Oakland, Maryland Short-Term Rental Market
Oakland, MD averaged a $544 ADR, 37.3% occupancy and $5,709 monthly revenue in September 2026.
Quick Answer: Oakland, Maryland is an active short-term rental market. average occupancy in the Deep Creek market area is 37%. average monthly revenue in the Deep Creek market area is $5,709. average daily rate in the Deep Creek market area is $544. 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, Maryland is the county seat of Garrett County, a town of 1,843 residents in far western Maryland just south of Deep Creek Lake. As of September 2026, the Oakland area STR market shows an average daily rate of $544, occupancy of 37.3% and average monthly revenue of $5,709 per listing. Compared with a year earlier, occupancy is up 20.8%, ADR is up 5.7% and revenue is up 19.6%, so the market is growing on both volume and price. Through the first nine months of 2026, occupancy averages 41.2%, ADR is $546 and monthly revenue is $6,312, ahead of the full 2025 figures of 39.6%, $535 and $5,869. Garrett County draws an estimated 1.4 million visitors a year. That is a county level figure, and no Oakland specific visitor count is published. Demand centers on Deep Creek Lake, Wisp Resort (the only ski area in Maryland) and state parks such as Swallow Falls and Deep Creek Lake State Park. The Oakland area STR market is almost entirely entire place rentals, with 2,000 entire place listings and 17 private rooms tracked. By bedroom count, 5 bedroom homes are the largest group at 774 listings, followed by 4 bedroom homes at 445 and 3 bedroom homes at 439, with 180 two bedroom and 178 one bedroom listings. Most hosts advertise on both major platforms: 1,606 listings appear on both Airbnb and Vrbo, 322 on Airbnb only and 89 on Vrbo only. The weight of large homes helps explain the high ADR. Occupancy is modest, which is typical of a drive to destination with sharp summer and winter peaks and quieter shoulder months.
Seasonal Patterns
| Month | Occupancy |
|---|---|
| Jan | 31% |
| Feb | 34% |
| Mar | 23% |
| Apr | 30% |
| May | 36% |
| Jun | 51% |
| Jul | 65% |
| Aug | 62% |
| 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 in Oakland and across Garrett County. Operators need a Transient Vacation Rental Unit (TVRU) license or short term rental registration from the Garrett County Department of Planning and Land Management. The county’s TVRU framework has been in place since 2006. Reported costs run from about $50 for a two year license up to about $250 when combined with new rental registration and a zoning permit, so confirm current amounts with the county. Licenses renew on a two year cycle. There is no annual cap on rental nights, and neither owner occupancy nor primary residence is required, so the process is the same for owner managed and professionally managed homes. A TVRU is a dwelling rented for 14 days or less, with a limit of eight bedrooms and occupancy of two persons per bedroom plus four additional guests. Standards include bedroom egress windows, one parking space per bedroom, bear proof trash containers, posted quiet hours from 10 pm to 8 am and emergency exit plans. Pools, hot tubs and wells carry extra certification or testing requirements. The county levies an 8% occupancy tax, and licensed operators file monthly reports. Garrett County has no countywide zoning, and the strictest standards apply in the Deep Creek Lake Watershed Zoning District. The Town of Oakland keeps its own zoning, so check both the county and the town before operating. Enforcement is rated moderate and is mostly complaint driven, with possible fines, suspension or revocation. No major overhaul was identified in the last 24 months.
Market Comparison
Oakland earns through rate rather than volume. The latest ADR is $544, while occupancy is 37.3%. Revenue of $5,709 per month reflects large homes, with 5 bedroom homes the biggest bedroom group among 2,017 tracked listings. Only July and August, at 65.1% and 62.1%, run above 60% occupancy. The StaySTRA market score for the Oakland area is 84.9 overall. Investability scores 97.64 and revenue growth scores 98.77, while regulation scores 71.81, rental demand 54.32 and seasonality 52.92. The lower seasonality and demand scores match the data above. Operators are concentrated among a few regional managers. Railey Vacations leads with 590 listings and a 4.62 rating, followed by Taylor-Made Deep Creek Vacations by Vtrips with 453 listings and a 4.5 rating. Vacasa has 97 listings, Red Barn Vacations has 91 with a 4.8 rating, and Prime Vacation Rentals has 44. Independent owners compete with large managers that hold a strong share of reviews.
Frequently Asked Questions About Oakland, Maryland
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