Vacation rentals in Highland Beach, MD

4 available vacation rental offers

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Up to $100$100 - 200From $200

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Best vacation rentals and Airbnb offers in Highland Beach, MD

Flag House Inn - Highland Beach, MD
9.2 ★ 94 reviews

Flag House Inn

B & B, Highland Beach

Flag House Inn is a b & b in Highland Beach, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Flag House Inn

Flag House Inn is a b & b in Highland Beach, 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 breakfast, free wifi, parking, fireplace, and bed and breakfast.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,385.

From$424/night
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Steps to Chesapeake Bay! 'Callaway Drive Retreat' - Highland Beach, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Highland Beach

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Highland Beach, with easy beach access, parking, and a quieter setting. This stay gives travelers a comfortable base…

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About Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Highland Beach, with easy beach access, parking, and a quieter setting. 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 heating.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,639.

From$145/night
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'callaway Drive Retreat' 3BR Home Near Water - Highland Beach, MD

'callaway Drive Retreat' 3BR Home Near Water

Cottage, Highland Beach

'callaway Drive Retreat' 3BR Home Near Water is a cottage in Highland Beach, with kitchen access, room for a group, and a quieter setting. This stay gives travelers a comfortable base for…

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About 'callaway Drive Retreat' 3BR Home Near Water

'callaway Drive Retreat' 3BR Home Near Water is a cottage in Highland Beach, with kitchen access, room for a group, and a quieter setting. 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 tv.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,702.

From$178/night
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The Inn at Tacaro Estate - Highland Beach, MD
9.6 ★ 15 reviews

The Inn at Tacaro Estate

B & B, Highland Beach

The Inn at Tacaro Estate is a b & b in Highland Beach, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About The Inn at Tacaro Estate

The Inn at Tacaro Estate is a b & b in Highland Beach, 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, free breakfast, pool, hot tub, and free wifi.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,643.

From$582/night
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