Gloucester 4+ bedroom Apartments, Vacation Rentals & More - 35 Rentals Available.
35 Vacation rentals
Filters applied: 4+ Bedrooms
Annisquam Singing Pines: Private riverfront setting & tidal dock.
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- Sleeps 10 10
- 3 nights min
- Ask about children
$670.00
from $670.00 / 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
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
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
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
$971.00
from $971.00 / 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
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
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
$572.00
from $572.00 / night
Seaside House: Good Harbor Beach and the Back Shore right outside
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
$633.00
from $633.00 / 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
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
$580.00
from $580.00 / 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
$1,105.00
from $1,105.00 / 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
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
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
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
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