Skip to content

Holiday rentals in Gloucester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Gloucester

Guests agree: these stays are highly rated for location, cleanliness, and more.

Perfect downtown location, close to everything
Entire flat · 4 guests · 2 beds · 1.5 bathrooms

Perfect downtown location, close to everythingWonderful downtown location, steps from restaurants, harbor, beach and train. This quintessential home has been updated for comfortable living, while retaining charming characteristics. A spacious kitchen and dining area, living room and half bath are located on the 1st floor, while upstairs 1 bedroom features a king bed, 2nd features a full, and the 3rd is a dedicated office with 2 desk stations. High speed internet, cable TV and washer/dryer are provided. Maximum of FOUR guests per town bylaw

Comfortable First Floor Room, Walk to ocean
SUPERHOST
Private room · 2 guests · 1 bed · 1 shared bathroom

Comfortable First Floor Room, Walk to oceanComfortable older home with updated bathrooms located two blocks from Atlantic Ocean’s Rocky shoreline and 1.5 miles to beautiful Good Harbor’s sandy beach. Downtown Gloucester is about 3 miles away with shops and restaurants.

5-minute walk to Back Beach in Beautiful Rockport
Entire flat · 5 guests · 3 beds · 1 bathroom

5-minute walk to Back Beach in Beautiful RockportNewly renovated apartment with private entrance (and peeks of the ocean) just a short walk to Back Beach and 10 minute walk to downtown Rockport. Stylish living room and kitchen with everything you need for your stay. Set up with one queen bedroom, two twin bedrooms (one with a trundle bed). Come enjoy the sights of Rockport - a quaint, New England seaside town. This apartment is one of two units in the home so we welcome guests who are quiet and very respectful of neighbors. 1 parking spot.

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Gloucester holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Gloucester

SUPERHOST
  1. Entire cabin
  2. Rockport
The Dogtown Cabin at Applecart Farm
₹21,621 per night
  1. Entire cottage
  2. Rockport
Quaint Oceanfront Cottage in Rockport MA
₹10,016 per night
SUPERHOST
  1. Entire cottage
  2. Gloucester
Robyn's Cottage at Plum Cove
₹14,732 per night
  1. Entire bungalow
  2. Gloucester
mermaid surf bungalow on good harbor beach
₹23,370 per night
  1. Entire flat
  2. Essex
Healing Essence
₹14,467 per night
SUPERHOST
  1. Entire guest house
  2. Gloucester
Plum Cove Cottage
₹13,174 per night
SUPERHOST
  1. Entire guest suite
  2. Rockport
Nature lovers retreat
₹6,359 per night
  1. Entire flat
  2. Manchester-by-the-Sea
NEW LISTING Serendipity Suite
₹18,548 per night
SUPERHOST
  1. Entire guest suite
  2. Rockport
King size studio Cape Ann retreat
₹8,299 per night
SUPERHOST
  1. Entire loft
  2. Rockport
Loft Apartment With Ocean Views
₹21,515 per night
  1. Entire house
  2. Rockport
Home Nestled in Country Gardens-300 Yards to Beach
₹42,395 per night
  1. Entire cottage
  2. Rockport
Periwinkle Cottage #1 -walk to everything!
₹13,036 per night

Nearby destinations