More Filters

Price per Night Range

$0
$1000+


Accommodations


Interest


Gloucester Vacation Rentals

27 Gloucester Vacation Rentals were found matching your criteria.



$600 - $950 /week
Captain John Stephens House: Sparkling new studio in the ...

  5 reviews   Add to Favorites

Condo: Studio, 1 Bathroom, Sleeps 2
Location: Gloucester, Massachusetts, United States


$583 - $583 /night
$2600 - $3500 /week
Welcome Home: Walk to Gloucester's historic harbor and be...

  1 reviews   Add to Favorites

Home: 5 Bedroom, 2.5 Bathroom, Sleeps 12
Location: Gloucester, Massachusetts, United States


$408 - $450 /night
$1750 - $2700 /week
Two Beaches: Immaculate single-level 3Br between Long Bea...

  5 reviews   Add to Favorites

Home: 3 Bedroom, 1.5 Bathroom, Sleeps 8
Location: Gloucester, Massachusetts, United States


$250 - $350 /night
$1250 - $1750 /week
Little Red House: Close to Gloucester's historic Stage Fo...

  30 reviews   Add to Favorites

Home: 3 Bedroom, 1 Bathroom, Sleeps 5
Location: Gloucester, Massachusetts, United States


$440 - $440 /night
$1800 - $2200 /week
Thurston Point: Waterfront rental with deepwater dock on ...

  20 reviews   Add to Favorites

Cottage: 3 Bedroom, 1.5 Bathroom, Sleeps 7
Location: Gloucester, Massachusetts, United States


$383 - $400 /night
$1650 - $2400 /week
Sunset Cottage: Direct waterfront with two decks on the A...

  15 reviews   Add to Favorites

Cottage: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Gloucester, Massachusetts, United States


$750 - $1140 /night
$3750 - $6100 /week
Strawberry Cove House: Multi-level waterfront home

  1 reviews   Add to Favorites

Home: 4 Bedroom, 3 Bathroom, Sleeps 10
Location: Gloucester, Massachusetts, United States


$220 - $231 /night
$1050 - $1600 /week
Garden by the Sea: Relax & enjoy wonderful coastal views....

  37 reviews   Add to Favorites

Apartment: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Gloucester, Massachusetts, United States


$450 - $610 /night
$2250 - $3050 /week
Water's Edge: Direct waterfront on picturesque Goose Cove...

  27 reviews   Add to Favorites

Home: 3 Bedroom, 3 Bathroom, Sleeps 8
Location: Gloucester, Massachusetts, United States


$470 - $508 /night
$2350 - $3050 /week
Beachmont: Easy access to Stagefort Park, Beaches & Downt...

  16 reviews   Add to Favorites

Home: 5 Bedroom, 2 Bathroom, Sleeps 9
Location: Gloucester, Massachusetts, United States


$700 - $920 /night
$3500 - $4600 /week
Annisquam Singing Pines: Private riverfront setting & tid...

  5 reviews   Add to Favorites

Home: 5 Bedroom, 2 Bathroom, Sleeps 10
Location: Gloucester, Massachusetts, United States



$4400 - $4875 /week
Seaside House: Good Harbor Beach and the Back Shore right...

  15 reviews   Add to Favorites

Home: 4 Bedroom, 2.5 Bathroom, Sleeps 10
Location: Gloucester, Massachusetts, United States



$1100 - $1200 /week
Cher Ami: Gleaming and immaculate condo just 0.3 mi to Cr...

  16 reviews   Add to Favorites

Condo: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Gloucester, Massachusetts, United States



$4500 - $4700 /week
Seacastle: Pet-friendly! Close to Coffin's Beach & Wingae...

Home: 5 Bedroom, 4.5 Bathroom, Sleeps 8
Location: Gloucester, Massachusetts, United States


$350 - $440 /night
$1750 - $2200 /week
Riverview: Freshly renovated home overlooking the Annisqu...

  1 reviews   Add to Favorites

Home: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Gloucester, Massachusetts, United States


$270 - $330 /night
$1250 - $1690 /week
Treehouse by the Sea: Stacy Boulevard, Downtown Glouceste...

  9 reviews   Add to Favorites

Condo: 2 Bedroom, 1.5 Bathroom, Sleeps 4
Location: Gloucester, Massachusetts, United States


$550 - $583 /night
$2500 - $3500 /week
Sea Fox: Custom-designed home with rights to private Coff...

  10 reviews   Add to Favorites

Home: 4 Bedroom, 3 Bathroom, Sleeps 8
Location: Gloucester, Massachusetts, United States


$380 - $460 /night
$1900 - $2300 /week
Good Harbor Escape: Swim or walk over to Good Harbor Beach!

  1 reviews   Add to Favorites

Home: 3 Bedroom, 1 Bathroom, Sleeps 6
Location: Gloucester, Massachusetts, United States


$1100 - $1200 /night
$5700 - $7200 /week
Oceanside at Good Harbor: Walk 0.2 mi to the white sands ...

  4 reviews   Add to Favorites

Home: 5 Bedroom, 3 Bathroom, Sleeps 9
Location: Gloucester, Massachusetts, United States


$840 - $1180 /night
$4125 - $5900 /week
Eastern Point on the Sea: Water views, private beach and ...

  2 reviews   Add to Favorites

Home: 4 Bedroom, 2.5 Bathroom, Sleeps 7
Location: Gloucester, Massachusetts, United States


$960 - $1320 /night
$4800 - $6600 /week
Bell View: Private tennis court and an in-law suite

  27 reviews   Add to Favorites

Condo: 6 Bedroom, 5.5 Bathroom, Sleeps 16
Location: Gloucester, Massachusetts, United States


$660 - $860 /night
$3300 - $4300 /week
Perrywinkle: Waterfront on Gloucester?s Rocky Neck.

Home: 4 Bedroom, 2 Bathroom, Sleeps 6
Location: Gloucester, Massachusetts, United States


$625 - $667 /night
$2800 - $4000 /week
Salt Island Views: Walking distance to Good Harbor & Long...

  2 reviews   Add to Favorites

Home: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Gloucester, Massachusetts, United States


$583 - $608 /night
$2700 - $3650 /week
Long Beach Place: Just steps from the white sand & surf.

  6 reviews   Add to Favorites

Condo: 3 Bedroom, 2.5 Bathroom, Sleeps 8
Location: Gloucester, Massachusetts, United States



$2600 - $3650 /week
Townhouse by the Sea: Close to the white sands and lively...

  1 reviews   Add to Favorites

Condo: 4 Bedroom, 2.5 Bathroom, Sleeps 8
Location: Gloucester, Massachusetts, United States


This map is intended to be used as a reference only.

Eastern Top Cities

Vacation Rental Deals and Specials

Find additional Vacation Rentals: