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  1. Home
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  3. Maryland
  4. Oakland

Oakland, Maryland

Short-Term Rental Market Data & Investment Analysis

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).

Avg Monthly Revenue
$5,709
↑ 18.8% YoY
37%
Occupancy
↑ 21.2% YoY
$544
Avg Daily Rate
↑ 8% YoY
78.5 days avg lead time3.2 avg length of stay

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.

Regulation72
Seasonality53
Investability98
Rental Demand54
Revenue Growth99

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

Monthly seasonal data for Oakland, Maryland
MonthOccupancy
Jan31%
Feb34%
Mar23%
Apr30%
May36%
Jun51%
Jul65%
Aug62%
Sep35%
Oct37%
Nov31%
Dec37%

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.

#OperatorListingsReviewsRating
1Railey Vacations5909,424★ 4.62
2Taylor-Made Deep Creek Vacations by Vtrips45312,116★ 4.50
3Vacasa976,082★ 4.43
4Red Barn Vacations911,646★ 4.80
5Prime Vacation Rentals44959★ 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 mix
ChannelShare
airbnb16%
vrbo4.4%
both79.6%

Investment Analysis

The full investment analysis for Oakland — gross-yield math against current home values, plus 5-year monthly revenue, nightly-rate, and occupancy trend charts — is available to StaySTRA Pro members and updates monthly. The figures shown elsewhere on this page are the free market snapshot.

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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

What is the average Airbnb nightly rate in Oakland, MD?
The average daily rate across all listings in September 2026 is $544. Entire homes average $545, professionally managed properties average $630 and luxury listings average $903.
What is the occupancy rate for short term rentals in Oakland, MD?
Occupancy was 37.3% in September 2026, up 20.8% from a year earlier. Occupancy peaks at 65.1% in July and falls to 23.3% in March.
How much can an Oakland, MD short term rental earn?
Across all listing types, Oakland short-term rentals average $5,709 per month. Breakdowns by property type, bedroom count, and season are available with StaySTRA Pro, or run a free address-level estimate with the StaySTRA Analyzer.
Do I need a permit for a short term rental in Oakland, MD?
Yes. A Transient Vacation Rental Unit license or short term rental registration from Garrett County is required, renewed every two years. Reported costs range from about $50 to about $250, and an 8% occupancy tax applies. There is no annual night cap and no owner occupancy requirement.
What is the gross yield on an Oakland, MD short term rental?
Annualized revenue of $56,681 against a typical home value of $282,202 gives a gross yield of 20.1%. At the median list price of $375,300 the ratio is about 15.1%. Both figures are before expenses.
When is the best time to rent out a home in Oakland, MD?
Occupancy in Oakland peaks in Jul (65%) and is softest in Mar (23%). Month-by-month rate and revenue figures are available with StaySTRA Pro.
How far ahead do guests book in Oakland, MD?
The average booking lead time is 78.5 days and the average stay is 3.23 nights, so peak dates are often booked about eleven weeks out.
Oakland, MarylandRev $5,709ADR $544Occ 37%Score B (85)

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Table of Contents

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Quick Facts: Deep Creek market area

Avg Daily Rate
$544
Occupancy Rate
37%
Avg Revenue/Mo
$5,709
Oakland Population
1,843

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