Gloucester 3-bedroom Apartments, Vacation Rentals & More - 34 Rentals Available.
34 Vacation rentals
Filters applied: 3+ Bedrooms
Strawberry Cove House: Multi-level waterfront home
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
$750
from $750 / night
Water's Edge: Direct waterfront on picturesque Goose Cove with dock
Gloucester House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
- Pet friendly
$450
from $450 / night
Bell View: Private tennis court and an in-law suite
Gloucester House
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 16 16
- Min stay varies
- Ask about children
- Air conditioning
$960
from $960 / night
Two Beaches: Immaculate single-level 3BR between Long Beach & Good Harbor
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$408
from $408 / night
Helena House: European flair, close to Plum Cove Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
- Pet friendly
$320
from $320 / night
Welcome Home: Walk to Gloucester's historic harbor and beaches.
Gloucester House
- 5 bedrooms 5
- 3 bathrooms
- Sleeps 12 12
- Min stay varies
- Ask about children
$520
from $520 / 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
$550
from $550 / night
Golden Sands at Good Harbor: Across the street from the beach
Gloucester Cottage
- 7 bedrooms 7
- 4 bathrooms
- Sleeps 12 12
- Min stay varies
- Ask about children
$1000
from $1000 / 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
$700
from $700 / night
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Gloucester Cottage
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
$440
from $440 / night
Seacastle: Pet-friendly! Close to Coffin's Beach & Wingaersheek.
Gloucester House
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Pet friendly
$643
from $643 / night
Long Beach House: Large, comfortable home just 285 feet from the white sands!
Gloucester House
- 5 bedrooms 5
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
- Pet friendly
$538
from $538 / night
Little Red House: Close to Gloucester's historic Stage Fort Park & beaches
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- Sleeps 5 5
- Min stay varies
- Ask about children
$250
from $250 / night
Beachmont: Easy access to Stagefort Park, Beaches & Downtown Gloucester
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- Sleeps 9 9
- Min stay varies
- Ask about children
- Pet friendly
$470
from $470 / 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
$1275
from $1275 / night
Rosemarc House: 180-degree ocean views & a private beach
Gloucester House
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$929
from $929 / night
Seaside House: Good Harbor Beach and the Back Shore right outside
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
$629
from $629 / night
Long Beach Place: Just steps from the white sand & surf.
Gloucester Apartment
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
$583
from $583 / night
River Breezes: Direct riverfront with incredible sunsets
Gloucester Cottage
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
$440
from $440 / night
Victorian House: Explore Rocky Neck's art galleries & restaurants
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
- Pet friendly
$467
from $467 / night
Annie's Place: Sweet cottage just 0.2 miles to Plum Cove Beach
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- Sleeps 6 6
- Min stay varies
- Ask about children
- Pet friendly
$250
from $250 / night
Eastern Point on the Sea: Water views, private beach and gorgeous sunrises
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
- Pet friendly
$840
from $840 / night
High Rock Cottage: Astounding views from every angle!
Gloucester House
- 6 bedrooms 6
- 5 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
$1100
from $1100 / night
Townhouse by the Sea: Close to the white sands and lively surf of Long Beach.
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$372
from $372 / night
Sand Song: Just 1 block to Good Harbor Beach
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
- Air conditioning
$572
from $572 / night
Wonson Cove House: Rocky Neck, Eastern Point and Beaches
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
- Pet friendly
$633
from $633 / 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
$1100
from $1100 / night
Barlovento, the Spanish name for windward, is also the name of one of Eastern
Gloucester Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
$1195
from $1195 / night
Ships Bell: Water views, fantastic sunsets & a swimming quarry
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
- Air conditioning
$459
from $459 / night
Step out into the backyard and swim over to Good Harbor Beach!
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- Sleeps 6 6
- 3 nights min
- Ask about children
$381
from $381 / night
Within minutes of Gloucester's fabled Stacy Boulevard and Stage Fort Park
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 3 nights min
- Ask about children
$310
from $310 / night
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 6 6
- 3 nights min
- Ask about children
$660
from $660 / night
Close to Heaven is only a ten minute walk to Long Beach!
Gloucester House
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
- Air conditioning
$580
from $580 / 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
$625
from $625 / night
Your search has been expanded 3.8 miles to include more rentals
Sage Hill: Easy access to both Gloucester & Rockport
Rockport House - 2.8 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Pet friendly
$438
from $438 / night
Directly on Long Beach Rockport MA
Rockport House - 3.3 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 14 14
- Min stay varies
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$250
from $250 / night
Ocean Front Cottage on Scenic Long Beach
Rockport Cottage - 3.3 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 10 10
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$200
from $200 / night
Sea Vagabond: Amazing water views & close to Long Beach
Rockport House - 3.4 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 9 9
- Min stay varies
- Ask about children
- Pet friendly
$235
from $235 / night
Rockport Village House: 3 floors of bright and sunny living space
Rockport House - 3.7 miles away
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$400
from $400 / night
Point de Chene: Direct waterfront historic home with incredible views
Rockport House - 3.8 miles away
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 12 12
- Min stay varies
- Ask about children
- Pet friendly
$780
from $780 / night
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