Vacation rentals in Oakland, MD

17 available vacation rental offers

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Best vacation rentals and Airbnb offers in Oakland, MD

Cozy Cape Cod Bungalow - Oakland, MD
10 ★ 4 reviews

Cozy Cape Cod Bungalow

Holiday Home, Oakland

Cozy Cape Cod Bungalow is a holiday home in Oakland, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Cozy Cape Cod Bungalow

Cozy Cape Cod Bungalow is a holiday home in Oakland, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kids friendly, kids friendly videos or books, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $971.

From$96/night
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2 Mi to Wineries: Calm Cottage on 90 Acres w/ Barn - Oakland, MD
10 ★ 2 reviews

2 Mi to Wineries: Calm Cottage on 90 Acres w/ Barn

Cottage, Oakland

2 Mi to Wineries: Calm Cottage on 90 Acres w/ Barn is a cottage in Oakland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 2 Mi to Wineries: Calm Cottage on 90 Acres w/ Barn

2 Mi to Wineries: Calm Cottage on 90 Acres w/ Barn is a cottage in Oakland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,783.

From$195/night
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Owings Mills Townhouse: 8 Mi to Liberty Reservoir! - Oakland, MD
8 ★ 1 reviews

Owings Mills Townhouse: 8 Mi to Liberty Reservoir!

Apartment, Oakland

Owings Mills Townhouse: 8 Mi to Liberty Reservoir! is a apartment in Oakland, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Owings Mills Townhouse: 8 Mi to Liberty Reservoir!

Owings Mills Townhouse: 8 Mi to Liberty Reservoir! is a apartment in Oakland, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,596.

From$282/night
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Two Story Queen Primary - Oakland, MD

Two Story Queen Primary

Holiday Home, Oakland

Two Story Queen Primary is a holiday home in Oakland, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Two Story Queen Primary

Two Story Queen Primary is a holiday home in Oakland, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and ac.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,290.

From$152/night
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Family-friendly vacation rentals in Oakland, MD

Plan a trip with stays that give families more room to spread out.

Near Shops & Parks: Dog-friendly Maryland Gem - Oakland, MD

Near Shops & Parks: Dog-friendly Maryland Gem

Cottage, Oakland

Near Shops & Parks: Dog-friendly Maryland Gem is a cottage in Oakland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Near Shops & Parks: Dog-friendly Maryland Gem

Near Shops & Parks: Dog-friendly Maryland Gem is a cottage in Oakland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,706.

From$426/night
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1 Mi to Main St! Family-friendly Reisterstown Home - Oakland, MD

1 Mi to Main St! Family-friendly Reisterstown Home

Cottage, Oakland

1 Mi to Main St! Family-friendly Reisterstown Home is a cottage in Oakland, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About 1 Mi to Main St! Family-friendly Reisterstown Home

1 Mi to Main St! Family-friendly Reisterstown Home is a cottage in Oakland, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,306.

From$467/night
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16 Mi to Baltimore: Spacious Home in Owings Mills! - Oakland, MD

16 Mi to Baltimore: Spacious Home in Owings Mills!

Cottage, Oakland

16 Mi to Baltimore: Spacious Home in Owings Mills! is a cottage in Oakland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 16 Mi to Baltimore: Spacious Home in Owings Mills!

16 Mi to Baltimore: Spacious Home in Owings Mills! is a cottage in Oakland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $6,303.

From$723/night
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