A harbor with boats, including a 'Whale Watch' and a 'Wejack' named boat.

Weekend getaways in Gloucester

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Find the best place to stay - Gloucester

Wingaersheek: private and public beaches, luxury home, extended family in Annisquam

Image of Wingaersheek: private and public beaches, luxury home, extended family in Annisquam

Premier Host

Sleeps 15 · 6 bedrooms · 3 bathrooms

Good Harbor Beach House - walk to beach, close to restaurants and shopping!

Image of Good Harbor Beach House - walk to beach, close to restaurants and shopping!

Premier Host

Sleeps 8 · 4 bedrooms · 2 bathrooms

Just steps away from Wingaersheek's 1.5-mile-long private beach with white dunes

Image of Just steps away from Wingaersheek's 1.5-mile-long private beach with white dunes

Premier Host

Sleeps 8 · 4 bedrooms · 2 bathrooms

Beach Life Bliss - steps to the beach

Image of Beach Life Bliss - steps to the beach

Premier Host

Sleeps 6 · 2 bedrooms · 2 bathrooms

Luxury 1900's romantic retreat steps from the beach - King Suite!

Image of Luxury 1900's romantic retreat steps from the beach - King Suite!

Premier Host

Sleeps 4 · 1 bedroom · 1 bathroom

Classic Coastal Family Home | Walk to Sea;King Bed

Image of Classic Coastal Family Home | Walk to Sea;King Bed

Premier Host

Sleeps 12 · 5 bedrooms · 2 bathrooms