Vacation Rentals in Gloucester, Massachusetts

50 Properties Available

Annisquam Singing Pines: Riverfront Splendor Private vacation home
Annisquam Singing Pines: Riverfront Splendor
$1706 / night
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Over By Good Harbor: Phenomenal views! Private vacation home
Over By Good Harbor: Phenomenal views!
$1223 / night
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Secluded, 180 Degree View Of Wingaersheek Beach From High Up On The Dunes Private vacation home
Secluded, 180 Degree View Of Wingaersheek Beach From High Up On The Dunes
$1179 / night
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NEW Rental: 2 min walk to Private Coffin's Beach Private vacation home
NEW Rental: 2 min walk to Private Coffin's Beach
$1093 / night
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Beautiful Harbor View Walk to Beach 3b2bKings4beds Private vacation home
Beautiful Harbor View Walk to Beach 3b2bKings4beds
$991 / night
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BRAND NEW, Complete renovation: 4-Bedroom, 3.5 Bath, private Annisquam Gem! Private vacation home
BRAND NEW, Complete renovation: 4-Bedroom, 3.5 Bath, private Annisquam Gem!
$970 / night
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Stay at Good Harbor Beach Private vacation home
Stay at Good Harbor Beach
$913 / night
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Golden Sands at Good Harbor: Just walk across the street to the beach. Private vacation home
Golden Sands at Good Harbor: Just walk across the street to the beach.
$912 / night
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Waterfront Home! Stunning sunsets, swimming, paddling! Private vacation home
Waterfront Home! Stunning sunsets, swimming, paddling!
$852 / night
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Long Beach & Private Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil Private vacation home
Long Beach & Private Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil
$825 / night
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Salt Island Views: 4-Season Beach House Private vacation home
Salt Island Views: 4-Season Beach House
$825 / night
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Two Beaches: Walk to Long Beach or Good Harbor! Private vacation home
Two Beaches: Walk to Long Beach or Good Harbor!
$799 / night
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Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family Private vacation home
Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family
$795 / night
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Best Beach House in Gloucester on a Private Beach! Welcome to Paradise! Private vacation home
Best Beach House in Gloucester on a Private Beach! Welcome to Paradise!
$791 / night
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Elegant Bayview Victorian Home - Walk to Beach Private vacation home
Elegant Bayview Victorian Home - Walk to Beach
$780 / night
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Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit Private vacation home
Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit
$698 / night
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Plaisance: Enjoy the best of Gloucester living. Private vacation home
Plaisance: Enjoy the best of Gloucester living.
$693 / night
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Gorgeous New Home w\/ Ocean Views- 2 Private Beaches Steps Away Private vacation home
Gorgeous New Home w\/ Ocean Views- 2 Private Beaches Steps Away
$614 / night
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Quaint Neighborhood \/ Close to Beaches Apartment
Quaint Neighborhood \/ Close to Beaches
$608 / night
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Sunset Cove: Waterfront home in Goose Cove section of Gloucester. Private vacation home
Sunset Cove: Waterfront home in Goose Cove section of Gloucester.
$602 / night
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Thurston Point: Waterfront rental with deepwater dock on Annisquam River! Private vacation home
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
$596 / night
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First Period Colonial Lodging in Gloucester MA Private vacation home
First Period Colonial Lodging in Gloucester MA
$596 / night
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5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade! Private vacation home
5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade!
$576 / night
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NEW \"The Mariner\" · 3BR\/2.5 Bth · Walk to Beach+Rocky Neck · Fenced Backyard Private vacation home
NEW \"The Mariner\" · 3BR\/2.5 Bth · Walk to Beach+Rocky Neck · Fenced Backyard
$575 / night
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Waterfront Home with Spectacular Viewsof the Annisquam River Private vacation home
Waterfront Home with Spectacular Viewsof the Annisquam River
$557 / night
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3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8 Private vacation home
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
$552 / night
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Close to Good Harbor Beach, 3 bedroom apartment Apartment
Close to Good Harbor Beach, 3 bedroom apartment
$546 / night
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Beautifully renovated OCEAN-FRONT luxury home on private beach Private vacation home
Beautifully renovated OCEAN-FRONT luxury home on private beach
$502 / night
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Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach! Condo
Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!
$491 / night
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Good Harbor Beach House - walk to beach, close to restaurants and shopping! Cottage
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
$489 / night
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Helena House: European flair, close to Plum Cove Beach. Private vacation home
Helena House: European flair, close to Plum Cove Beach.
$482 / night
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Stay at Niles Beach S Private vacation home
Stay at Niles Beach S
$480 / night
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The Harborview - Luxury 2 bedroom condo in Downtown Gloucester Condo
The Harborview - Luxury 2 bedroom condo in Downtown Gloucester
$475 / night
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5-star home with quick walk to 2 beaches!! Private vacation home
5-star home with quick walk to 2 beaches!!
$469 / night
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Charming cottage on seaside estate offers gorgeous views, private beaches Cottage
Charming cottage on seaside estate offers gorgeous views, private beaches
$455 / night
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~Walk to Good Harbor Beach: Adorable 4 bedroom\/2 bath Dog Friendly~AC-Summer fun Private vacation home
~Walk to Good Harbor Beach: Adorable 4 bedroom\/2 bath Dog Friendly~AC-Summer fun
$453 / night
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Renovated Gloucester home, walk to the Boulevard, town and train Private vacation home
Renovated Gloucester home, walk to the Boulevard, town and train
$429 / night
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Elegant Bayview Victorian Home; walk to beach Private vacation home
Elegant Bayview Victorian Home; walk to beach
$427 / night
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Long Beach Suites: Ocean Views Apartment
Long Beach Suites: Ocean Views
$416 / night
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Long Beach Suites: 3 Mins Toes To Sand! Apartment
Long Beach Suites: 3 Mins Toes To Sand!
$412 / night
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Cape Ann Reset Private vacation home
Cape Ann Reset
$399 / night
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WATERFRONT- River & Harbors views, Walking Distance to Downtown, Beaches & Park Condo
WATERFRONT- River & Harbors views, Walking Distance to Downtown, Beaches & Park
$397 / night
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Ocean View - Great Location | Beautiful, Warm & Spacious. Private vacation home
Ocean View - Great Location | Beautiful, Warm & Spacious.
$379 / night
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Dog-Friendly, Waterfront Home with High-Speed WiFi, W\/D, & Two Decks Private vacation home
Dog-Friendly, Waterfront Home with High-Speed WiFi, W\/D, & Two Decks
$374 / night
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Jewel Box: A gem of a rental home close to Good Harbor Beach. Private vacation home
Jewel Box: A gem of a rental home close to Good Harbor Beach.
$364 / night
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Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe. Apartment
Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.
$336 / night
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Steps to Wingaersheek's Private 1.5 Mile White Dune Beach Private vacation home
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach
$318 / night
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Long Beach Suites Apart-hotel
Long Beach Suites
$314 / night
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3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach Private vacation home
3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach
$300 / night
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Family Friendly Townhouse 75 steps from Long Beach Private vacation home
Family Friendly Townhouse 75 steps from Long Beach
$290 / night
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