Gloucester 2-bedroom Apartments, Vacation Rentals & More - 71 Rentals Available.
71 Vacation rentals
Filters applied: 2+ Bedrooms
Water's Edge: Direct waterfront on picturesque Goose Cove with dock
Gloucester House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- 3 nights min
- Ask about children
- Air conditioning
- Pet friendly
$450.00
from $450.00 / night
Golden Sands at Good Harbor: Across the street from the beach
Gloucester Cottage
- 7 bedrooms 7
- 3 bathrooms
- Sleeps 12 12
- Min stay varies
- Ask about children
$1,010.00
from $1,010.00 / night
Long Beach Place: Just steps from the white sand & surf.
Gloucester Apartment
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
$588.00
from $588.00 / night
Welcome Home: Walk to Gloucester's historic harbor and beaches.
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- Sleeps 12 12
- Min stay varies
- Ask about children
$545.00
from $545.00 / night
Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches
Gloucester House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Ask about children
- Pet friendly
$280.00
from $280.00 / night
Beachmont: Easy access to Stage Fort Park, Beaches, and Downtown Gloucester
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- Sleeps 9 9
- Min stay varies
- Ask about children
- Pet friendly
$480.00
from $480.00 / night
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 7 7
- 3 nights min
- Ask about children
$650.00
from $650.00 / night
Two Beaches: Walk to Long Beach or Good Harbor!
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- Sleeps 8 8
- Min stay varies
- Ask about children
$463.00
from $463.00 / night
Good Harbor Escape: Swim or walk over to Good Harbor Beach!
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- Sleeps 6 6
- 3 nights min
- Ask about children
$350.00
from $350.00 / night
Bell View: Private tennis court and an in-law suite.
Gloucester House
- 6 bedrooms 6
- 5 bathrooms
- Sleeps 16 16
- Min stay varies
- Ask about children
- Air conditioning
$970.00
from $970.00 / night
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Gloucester Cottage
- 3 bedrooms 3
- 1 bathroom
- Sleeps 7 7
- Min stay varies
- Ask about children
$480.00
from $480.00 / night
Sea Fox: Custom-designed home with rights to private Coffins Beach
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
$563.00
from $563.00 / night
Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!
Gloucester Apartment
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Ask about children
$230.00
from $230.00 / night
Cher Ami: West Gloucester condo just 0.3 mi to Cressy's Beach.
Gloucester House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 14 nights min
- Ask about children
$160.00
from $160.00 / night
River Breezes: Direct riverfront with incredible sunsets
Gloucester Cottage
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
$450.00
from $450.00 / night
Beach Stone Cottage: Just feet from the white sands of Good Harbor Beach
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 3 nights min
- Ask about children
- Pet friendly
$640.00
from $640.00 / night
Annisquam Singing Pines: Private riverfront setting & tidal dock.
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- Sleeps 10 10
- 3 nights min
- Ask about children
$690.00
from $690.00 / night
Boulevard Bungalow: Steps away from Gloucester's fabled Stacy Boulevard.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 3 nights min
- Ask about children
$325.00
from $325.00 / night
Wonson Cove House: Rocky Neck, Eastern Point and Beaches
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
- Pet friendly
$672.00
from $672.00 / night
Long Beach House: Large, comfortable home just 285 feet from the white sands!
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
- Pet friendly
$482.00
from $482.00 / night
Seaside House: Good Harbor Beach and the Back Shore right outside
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
$920.00
from $920.00 / night
Cool Cove: Wingaersheek Beach plus your own private beach & all those views!
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$1,280.00
from $1,280.00 / night
Grandview: Elegant Estate in Annisquam with water views & beach access.
Gloucester House
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 12 12
- 3 nights min
- Ask about children
$1,075.00
from $1,075.00 / night
Rosemarc House: 180-degree ocean views & a private beach
Gloucester House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$1,433.00
from $1,433.00 / night
Sunset Cove: Waterfront home in Goose Cove section of Gloucester
Gloucester House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
$530.00
from $530.00 / night
Diamond in the Sky: Upscale townhouse near Good Harbor Beach.
Gloucester Condo
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 7 7
- 3 nights min
- Ask about children
- Air conditioning
$765.00
from $765.00 / night
Strawberry Cove House: Multi-level waterfront home
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- 3 nights min
- Ask about children
$940.00
from $940.00 / night
Little Red House: Close to Gloucester's historic Stage Fort Park & beaches
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- Sleeps 5 5
- 3 nights min
- Ask about children
$275.00
from $275.00 / night
Salt Island Views: Walking distance to Good Harbor & Long Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$672.00
from $672.00 / night
High Rock Cottage: Astounding views from every angle!
Gloucester House
- 6 bedrooms 6
- 4 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
$1,083.00
from $1,083.00 / night
Eastern Point on the Sea: Water views, private beach and gorgeous sunrises
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 7 7
- 3 nights min
- Ask about children
- Pet friendly
$870.00
from $870.00 / night
Hawthorne House: Downtown Gloucester, convenient for exploring Cape Ann.
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- Sleeps 4 4
- 28 nights min
- Ask about children
- Air conditioning
$135.00
from $135.00 / night
Oceanside at Good Harbor: Walk 0.2 mi to the white sands of Good Harbor Beach
Gloucester House
- 5 bedrooms 5
- 3 bathrooms
- Sleeps 9 9
- Min stay varies
- Ask about children
$1,110.00
from $1,110.00 / night
On the River: Spectacular views of the Mill River, with access for swimming.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 7 7
- 3 nights min
- Ask about children
$435.00
from $435.00 / night
Family Tides: Only a half-mile from Good Harbor Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$522.00
from $522.00 / night
Barlovento, the Spanish name for windward, is also the name of one of Eastern
Gloucester Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- 3 nights min
- Ask about children
$1,205.00
from $1,205.00 / night
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