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28 places to stay

SUPERHOSTRating 4.98 out of 5
Entire cottage · 1 bed
SplashLanding Private Beach Getaway in Gloucester
Gloucester · MA
Entire house · 5 beds
Gloucester Waterfront Home
Gloucester · MA
Rating 4.44 out of 5
Entire cottage · 7 beds
Cottage on Private Coffin or Wingaersheek Beach
Gloucester · MA
Rating 4.95 out of 5
Private room · 1 bed
A peaceful retreat in Annisquam
Gloucester · MA
Entire house · 6 beds
BEACH HOUSE RIGHT ON THE WATER, EXQUISITE SUNSETS
Essex · MA
Rating 4.92 out of 5
Entire flat · 4 beds
Healing Essence
Gloucester · MA
Entire cottage · 7 beds
NEW! Oceanview Gloucester Cottage w/Private Beach!
Gloucester · MA
Rating 5.0 out of 5
Entire flat · 2 beds
Steps from White Sands of Private Beach
Gloucester · MA
Entire house · 6 beds
Gloucester Beach Home w/Ocean Views!
Gloucester · MA
Rating 4.93 out of 5
Entire apartment · 6 beds
Family beach getaway.
Gloucester · MA
Rating 4.67 out of 5
Entire house · 4 beds
Wingaersheek Beach House - 3 minute walk to beach
Gloucester · MA
Rating 5.0 out of 5
Entire house · 8 beds
Sea Fox House - Sea Fox House
Gloucester · MA
Rating 4.84 out of 5
Entire house · 4 beds
Relax: 8 minute walk to a huge private beach!!!
Gloucester · MA
Entire house · 5 beds
Wingaersheek Sunrise - Wingaersheek Sunrise
Gloucester · MA
Rating 5.0 out of 5
Entire house · 9 beds
Wingaersheek Luxury Beach House Gloucester
SUPERHOSTRating 5.0 out of 5
Entire cottage · 1 bed
PrivateBeach for 2 Adults, Gloucester MA SquishInn
Gloucester · MA
Entire house · 6 beds
Gloucester Beach Home w/Ocean Views!
SUPERHOSTRating 4.87 out of 5
Entire house · 8 beds
Wingaersheek Beach House (Private)
118 of 28 Rentals
Enter dates to see full pricing. Additional fees apply. Taxes may be added. Free cancellation only applicable within 48 hours from booking.