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Gloucester vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Gloucester

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Rental unit in Gloucester
Beautifully remodeled unit in heart of Gloucester
Enjoy your stay in the heart of Gloucester close to everything this great town has to offer. This unit was completely remodeled in 2022. Two shorts blocks from Main Street in Gloucester and all of its wonderful restaurants and shops. Three blocks from the Beauport Hotel - perfect for wedding guests not staying at that location. This unit has new floors, countertops, appliances and fixtures and is freshly painted (no VOC paint). You will love this unit and location for your visit.
$190 per night
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Guest suite in Gloucester
Sunsets at the Seawall - A Coastal Hideaway
Beautiful, serene studio apartment steps from the water & colorful sunsets of Lane’s Cove in Gloucester. Includes kitchen, bathroom & comfortable bedroom with separate sitting area. A private patio just outside has a tabletop grill & an outdoor dining area. A short walk to Lane’s Cove, Plum Cove Beach, or the North Woods. A 10-20 min drive will take you to downtown Rockport , or Gloucester, for great seafood, art, and shopping! Enjoy a restful retreat or find adventure on Cape Ann!
$150 per night
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Rental unit in Rockport
The Bookstore|2 Private Parking Spots|2 King Beds
• Newly furnished and professionally designed space! • Steps to Front Beach, Bearskin Neck cafes, restaurants, boutiques, art shops, and the Shalin Liu Performance Center. • Private off street parking spot for 2 cars • High Speed Wi-Fi and 4K Smart TV • 10 minute walk from commuter rail to Boston • Smart TV equipped to stream all your favorites • Fully stocked and renovated kitchen • 2 Comfortable KING size memory foam beds • Convenient EV charging right across the street!
$201 per night

Stay near Gloucester's top sights

Cape Ann Whale Watch41 locals recommend
7 Seas Whale Watch19 locals recommend
Beauport Hotel Gloucester35 locals recommend
Stage Fort Park and Beach47 locals recommend
Causeway Restaurant41 locals recommend
Cape Ann Museum69 locals recommend

Gloucester beach vacation rentals

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Guest suite in Gloucester
Walk to Good Harbor Beach and Downtown Gloucester
$150 per night
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Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
$114 per night
Rental unit in Gloucester
The Summer House
$187 per night
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Condo in Gloucester
Key West Vibe,PrivatePatio,New Reno,WalkDWNTN
$147 per night
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Loft in Rockport
Loft Apartment With Ocean Views
$269 per night
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Rental unit in Gloucester
Long Beach Suites: Steps To Beach, Newly Built
$181 per night
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Rental unit in Rockport
1BR|Private Deck with Ocean Views|King Bed|Parking
$160 per night
Guest suite in Gloucester
Beachside~at Good Harbor Beach 2 person 1 bedroom.
$257 per night
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Guest suite in Rockport
Halibut Point State Park. Nature Lovers Retreat
$115 per night
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Home in Annisquam
Water views! Booking fall/holidays now
$239 per night
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Condo in Rockport
Dream waterfront town center 1 bedroom apartment
$224 per night
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Condo in Gloucester
Boho Beach Condo Perfect for Ocean Escape
$246 per night

Gloucester house rentals

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Home in Gloucester
Woodland Retreat|Firepit|Grill|Outdoor Shower
$220 per night
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Home in Gloucester
Wonderful Rocky Neck home on Gloucester harbor
$374 per night
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Private room in Gloucester
Room 1: The Lavender room at the Beach Rose
$177 per night
Home in Gloucester
Steps to Harbor, Park, Beach and Boardwalk
$170 per night
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Home in Gloucester
Antique Cottage|PRIVATE SAUNA|Beach|Firepit+Grill
$211 per night
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Home in Gloucester
Seaside Home Minutes to Rockport and Gloucester!
$182 per night
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Private room in Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
$119 per night
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Home in Gloucester
NEW 3BR Harborside Home|Backyard+Grill|Ocean Views
$258 per night
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Home in Gloucester
Charming Harbor View Home
$100 per night
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Private room in Gloucester
Walking Distance to Beach Private 2 Bedroom Space
$175 per night
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Private room in Gloucester
Award Winning View from Portagee Hill
$95 per night
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Home in Rockport
Cozy & Quaint 2 Bedroom
$169 per night

Beach house rentals in Gloucester

Home in Gloucester
Beautiful Seaside Cottage in Gloucester
$260 per night
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Private room in Gloucester
Cozy Suite with Private Bath
$175 per night
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Home in Rockport
NEW 2BR Home|Minutes to Downtown Rockport+Beach
$212 per night
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Home in Gloucester
Gloucester getaway ocean escape
$226 per night
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Home in Gloucester
Beach Life Bliss - steps to the beach
$203 per night
Home in Gloucester
Entire House in Beautiful, Historic Gloucester
$150 per night
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Home in Gloucester
Hidden Gem: 3 Minute Walk to Beach
$301 per night
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Private room in Gloucester
Room 2: The Seaglass at the Beach Rose
$190 per night
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Home in Gloucester
Seaside Escape
$293 per night
Home in Gloucester
Classic 3BR | Patio | Firepit | W/D
$177 per night
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Private room in Rockport
The Smith House in Rockport, a seaside village
$100 per night
Private room in Rockport
Large master bdrm, prvt bath, deck + kitchenette
$70 per night
  1. Airbnb
  2. United States
  3. Massachusetts
  4. Essex County
  5. Gloucester