Gloucester Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

River Breezes: Direct riverfront with incredible sunsets

Gloucester
Enjoy the views of the sparkling Annisquam River, lovely Wingaersheek Beach and the Annisqaum Yacht ...
Cottage 3 / 3.5 / 7

*
Online booking available

$450 - $497
Per Night

$2230 - $2980
Per Week

High Rock Cottage: Astounding views from every angle!

Gloucester
This luxurious vacation rental home is situated on the highest point of Brier Neck with astounding o...
Home 6 / 4.5 / 10

*
Online booking available

$7580 - $7730
Per Week

Reeds Wharf is a charming one BR condo, overlooking Smith...

Gloucester
Reeds Wharf is a charming one BR condo, overlooking Smith Cove. This charming condominium is locate...
Condo 1 / 1 / 4

*
Online booking available

$1258 - $1507
Per Week

Eastern Point on the Sea: Water views, private beach and ...

Gloucester
Eastern Point on the Sea: Water views, private beach and gorgeous sunrises Enjoy views of Glouceste...
Home 4 / 2.5 / 7

*
Online booking available

$870 - $1175
Per Night

$4330 - $5855
Per Week

Garden by the Sea: Relax & enjoy wonderful coastal views....

Gloucester
Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach! Relax and take in wond...
Apartment 2 / 1 / 4

*
Online booking available

$230 - $230
Per Night

$1080 - $1730
Per Week

Oceanside at Good Harbor: Walk 0.2 mi to the white sands ...

Gloucester
Oceanside at Good Harbor: Walk 0.2 mi to the white sands of Good Harbor Beach Oceanside at Good Har...
Home 5 / 3 / 9

*
Online booking available

$1110 - $1205
Per Night

$5730 - $7230
Per Week

Long Beach Place: Just steps from the white sand & surf.

Gloucester
Just 10 yards from the white sands and lively surf of Long Beach, this vacation rental condo sleeps ...
Condo 3 / 2.5 / 8

*
Online booking available

$588 - $613
Per Night

$2730 - $3580
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

$280 - $340
Per Night

$1280 - $1720
Per Week

Rosemarc House: 180-degree ocean views & a private beach

Gloucester
Rosemarc House has stairs that take you directly onto the private portion of Good Harbor Beach. This...
Home 3 / 3.5 / 6

*
Online booking available

$10030 - $10030
Per Week

Diamond in the Sky: Upscale townhouse near Good Harbor Be...

Gloucester
Diamond in the Sky: Upscale townhouse near Good Harbor Beach. New in 2018! Indulge in luxury at Dia...
Condo 3 / 3 / 7

*
Online booking available

$585 - $750
Per Night

$3330 - $3730
Per Week

Sunset Cove: Waterfront home in Goose Cove section of Glo...

Gloucester
Sunset Cove: Waterfront home in Goose Cove section of Gloucester Waterfront on the Annisquam River ...
Home 2 / 2.5 / 6

*
Online booking available

$530 - $630
Per Night

$2630 - $3455
Per Week

Welcome Home: Walk to Gloucester's historic harbor and be...

Gloucester
Welcome Home: Walk to Gloucester's historic harbor and beaches. Enjoy the ambiance of Victorian Glo...
Home 5 / 2.5 / 12

*
Online booking available

$545 - $588
Per Night

$2705 - $3530
Per Week

Boulevard Bungalow: Steps away from Gloucester's fabled S...

Gloucester
Boulevard Bungalow: Steps away from Gloucester's fabled Stacy Boulevard. Located right around the c...
Home 3 / 2 / 6

*
Online booking available

$325 - $370
Per Night

$1605 - $1830
Per Week

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

Gloucester
Annisquam Singing Pines: Private riverfront setting & tidal dock. Imagine a summer of bliss, swimmi...
Home 5 / 2 / 10

*
Online booking available

$690 - $860
Per Night

$3430 - $4280
Per Week

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

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

*
Online booking available

$630 - $980
Per Week

Beach Stone Cottage: Just feet from the white sands of Go...

Gloucester
Beach Stone Cottage: Just feet from the white sands of Good Harbor Beach This lovely beach house ha...
Home 3 / 2 / 6

*
Online booking available

$640 - $880
Per Night

$3180 - $4380
Per Week

Grandview: Elegant Estate in Annisquam with water views &...

Gloucester
Grandview: Elegant Estate in Annisquam with water views & beach access. Located in the heart of Ann...
Home 5 / 4.5 / 12

*
Online booking available

$1024 - $1810
Per Night

$7130 - $9030
Per Week

Two Beaches: Walk to Long Beach or Good Harbor!

Gloucester
Ideally situated between two of Cape Ann's most beautiful beaches, this ideal vacation rental home i...
Home 3 / 1.5 / 8

*
Online booking available

$463 - $513
Per Night

$1980 - $3080
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 This comfortable recentl...
Home 3 / 1 / 5

*
Online booking available

$275 - $360
Per Night

$1355 - $1780
Per Week

Helen's Way: Charming Gloucester apartment near Good Harb...

Gloucester
Helen's Way: Charming Gloucester apartment near Good Harbor Beach. Helen's Way is a quaint and tast...
Apartment 1 / 1 / 4

*
Online booking available

$220 - $300
Per Night

$1080 - $1480
Per Week

Perrywinkle: Waterfront on Gloucester?s Rocky Neck.

Gloucester
Waterfront on Gloucester?s Rocky Neck. Swim from your private beach or from your tidal dock and enjo...
Home 4 / 2 / 7

*
Online booking available

$650 - $870
Per Night

$3230 - $4330
Per Week

On the River: Spectacular views of the Mill River, with a...

Gloucester
On the River: Spectacular views of the Mill River, with access for swimming. This riverfront vacati...
Home 3 / 2.5 / 7

*
Online booking available

$435 - $550
Per Night

$2155 - $2730
Per Week

Family Tides: Only a half-mile from Good Harbor Beach.

Gloucester
Located in a quiet, leafy neighborhood, Family Tides offers convenience and comfort, just a half-mil...
Home 3 / 2 / 8

*
Online booking available

$522 - $522
Per Night

$3030 - $3130
Per Week

Good Harbor Escape: Swim or walk over to Good Harbor Beach!

Gloucester
For the adventurer, this home is a short swim away from Good Harbor Beach. Located on the edge of a ...
Home 3 / 1 / 6

*
Online booking available

$350 - $470
Per Night

$1730 - $2330
Per Week

Squam Cottage

Gloucester
Located in the heart of the quaint and picturesque village of Annisquam, this sweet vacation home is...
Home 3 / 2 / 7

*
Online booking available

$400 - $500
Per Night

$1980 - $2480
Per Week

 

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