Gloucester Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

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

Gloucester
Sunset Cove: Waterfront home in Goose Cove section of Gloucester A riverfront property on the Annis...
Home 2 / 2.5 / 6

*
Online booking available

$530 - $630
Per Night

$2630 - $3455
Per Week

Bell View: Private tennis court and an in-law suite.

Gloucester
Your Gloucester vacation experience awaits you in this spacious and versatile vacation home. Bell Vi...
Condo 6 / 5.5 / 16

*
Online booking available

$970 - $1330
Per Night

$4830 - $6630
Per Week

Strawberry Cove House: Multi-level waterfront home

Gloucester
Your family will love this extraordinary waterfront vacation rental home with spectacular views. Set...
Home 4 / 3 / 10

*
Online booking available

$940 - $1236
Per Night

$4680 - $6130
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

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

Golden Sands at Good Harbor: Across the street from the b...

Gloucester
Golden Sands at Good Harbor: Across the street from the beach Golden Sands is the quintessential tu...
Cottage 7 / 3.5 / 12

*
Online booking available

$1010 - $1405
Per Night

$5005 - $7180
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 - $371
Per Night

$1605 - $1830
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 - $1967
Per Night

$7130 - $9730
Per Week

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

Gloucester
New for 2018! Located in a quiet, leafy neighborhood, Family Tides offers convenience and comfort, j...
Home 3 / 2 / 8

*
Online booking available

$522 - $645
Per Night

$3030 - $3230
Per Week

Thurston Point: Waterfront rental with deepwater dock on ...

Gloucester
Thurston Point: Waterfront rental with deepwater dock on Annisquam River! Get away from it all and ...
Cottage 3 / 1.5 / 7

*
Online booking available

$480 - $505
Per Night

$2130 - $2573
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

$1507 - $1509
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 - $330
Per Night

$1080 - $1777
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 - $3626
Per Week

Barlovento, the Spanish name for windward, is also the na...

Gloucester
Barlovento, the Spanish name for ?windward,? is also the name of this stunning vacation rental home,...
Villa 5 / 5.5 / 10

*
Online booking available

$1205 - $1690
Per Night

$6005 - $8661
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

$765 - $937
Per Night

$3805 - $4587
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

$180 - $190
Per Night

$630 - $980
Per Week

Squam Cottage

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

*
Online booking available

$400 - $500
Per Night

$1980 - $2480
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

Long Beach House: Large, comfortable home just 285 feet f...

Gloucester
Long Beach House: Large, comfortable home just 285 feet from the white sands! This large and comfor...
Home 5 / 2.5 / 10

*
Online booking available

$481 - $690
Per Night

$2630 - $3678
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

Beachmont: Easy access to Stage Fort Park, Beaches, and D...

Gloucester
Beachmont: Easy access to Stage Fort Park, Beaches, and Downtown Gloucester This stately Victorian ...
Home 5 / 2 / 9

*
Online booking available

$480 - $610
Per Night

$2380 - $3043
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 - $597
Per Night

$2705 - $3575
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 - $10116
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

 

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