A cobblestone street lined with colorful buildings, a prominent tower, and flags.

Highlands houses

We found 169 houses — enter your dates for availability

Explore Highlands house rentals

Image of Highlands cottage across the street from Proving Ground and Twin Lights Marina

Premier Host

Highlands cottage across the street from Proving Ground and Twin Lights Marina

Sleeps 3 · 1 bedroom · 1 bathroom

Image of Little Haven (B) — Bungalows, Private Beach

Little Haven (B) — Bungalows, Private Beach

Sleeps 6 · 3 bedrooms · 1 bathroom

Image of Ground floor water side 1-bedroom cottage. Rocking chair front porch. No stairs

Premier Host

Ground floor water side 1-bedroom cottage. Rocking chair front porch. No stairs

Sleeps 4 · 1 bedroom · 1 bathroom

Image of Coastal Home With 360 Degree Rooftop Deck ~ Outstanding Views!

Premier Host

Coastal Home With 360 Degree Rooftop Deck ~ Outstanding Views!

Sleeps 5 · 2 bedrooms · 2 bathrooms

Image of A Great Escape !! One Of A Kind Waterfront Cottage.

Premier Host

A Great Escape !! One Of A Kind Waterfront Cottage.

Sleeps 3 · 1 bedroom · 1 bathroom

Brand new home by ferry, beach, shops, and trails

Sleeps 6 · 3 bedrooms · 1+ bathroom

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