Gloucester Vacation Rental Getaways


Refine Your Search
Check-In 
calendar

Check-Out
calendar
  • Property Options
  • Amenities
  • Location Type
  • Bed
  • Bath
  • Sleeps
Max Price Per Week $
  • Special Offers
  • Online Booking
  • Home/Villa
  • Cottage/Cabin
  • Condo/Townhome
  • Bed & Breakfast
  • Apt/Room/Suite
  • Air Conditioning
  • Washer/Dryer
  • Full Kitchen
  • Satellite/Cable TV
  • Handicap Access
  • High Speed Internet
  • Elevator
  • Maid Service
  • Garage Parking
  • Pets Allowed
  • Private Pool
  • Pool Access
  • Hot Tub
  • Fireplace
  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
  • Golf nearby
  • Ocean Front
  • Ocean View
  • Lake Front
  • Lake View
  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

Annisquam Singing Pines: Private riverfront setting & tid...

Gloucester
Annisquam Singing Pines: Private riverfront setting & tidal dock. New in 2016! Enjoy the best suns...
Home 5 / 2 / 10

*
Online booking available

$675 - $990
Per Night

$3375 - $4950
Per Week

Marina Place: Walk to Good Harbor from this newly built a...

Gloucester
Marina Place: Walk to Good Harbor from this newly built apartment. Walk to Good Harbor in 7 minutes...
Condo 1 / 1 / 4

*
Online booking available

$200 - $250
Per Night

$950 - $1250
Per Week

Two Beaches: Immaculate 3 bed/1.5 bath home between Long ...

Gloucester
Two Beaches: Immaculate 3 bed/1.5 bath home between Long and Good Harbor! New in 2016! Ideally situ...
Home 3 / 1.5 / 8

*
Online booking available

$330 - $480
Per Night

$1650 - $2400
Per Week

Victorian House: Explore Rocky Neck's art galleries & res...

Gloucester
Victorian House: Explore Rocky Neck's art galleries & restaurants A tastefully renovated vacation h...
Home 3 / 2 / 6

*
Online booking available

$2000 - $2800
Per Week

Griffin's Getaway: Sweet 2 Br apartment with views of Ips...

Gloucester
Griffin's Getaway: Sweet 2 Br apartment with views of Ipswich Bay This sweet two bedroom vacation r...
Apartment 2 / 1 / 3

*
Online booking available

$700 - $850
Per Week

Captain John Stephens House: Sparkling new studio in the ...

Gloucester
Captain John Stephens House: Sparkling new studio in the heart of Gloucester New in 2016! Captain J...
Condo 0 / 1 / 2

*
Online booking available

$500 - $850
Per Week

Little Red House: Close to Gloucester's historic Stage Fo...

Gloucester
Little Red House: Close to Gloucester's historic Stage Fort Park & beaches Enjoy this comfortable r...
Home 3 / 1 / 5

*
Online booking available

$250 - $350
Per Night

$1200 - $1750
Per Week

Water's Edge Too: Direct waterfront on the banks of pictu...

Gloucester
Water's Edge Too: Direct waterfront on the banks of picturesque Goose Cove Featuring a waterfront l...
Cottage 2 / 2 / 6

*
Online booking available

$240 - $330
Per Night

$1200 - $1650
Per Week

Annie's Place: Sweet cottage just 0.2 miles to Plum Cove ...

Gloucester
Annie's Place: Sweet cottage just 0.2 miles to Plum Cove Beach A delightful vacation home situated ...
Home 3 / 1 / 6

*
Online booking available

$230 - $340
Per Night

$1150 - $1700
Per Week

Beach Walk: Good Harbor Beach footbridge just steps away!

Gloucester
This Friday to Friday vacation rental is right at Good Harbor Beach. Step out the door, walk over th...
Apartment 1 / 1 / 3

*
Online booking available

$1275 - $1400
Per Week

Captains Watch: Close to the action of the Boulevard & do...

Gloucester
Captains Watch: Close to the action of the Boulevard & downtown Gloucester Captain's Watch House is...
Home 3 / 1.5 / 6

*
Online booking available

$1150 - $1700
Per Week

Helena House: European flair, close to Plum Cove Beach.

Gloucester
This delightful 3 bedroom, 1.5 bath Queen Anne-style vacation rental home is bright and cheery and j...
Home 3 / 1.5 / 6

*
Online booking available

$320 - $360
Per Night

$1250 - $1815
Per Week

Treehouse by the Sea: Stacy Boulevard, Downtown Glouceste...

Gloucester
Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches Enjoy the views, breezes an...
Condo 2 / 1.5 / 4

*
Online booking available

$250 - $335
Per Night

$1250 - $1690
Per Week

 

More Getaway Locations and Properties