Gloucester 2-bedroom Apartments, Vacation Rentals & More - 58 Rentals Available.
58 Vacation rentals
Filters applied: 2+ Bedrooms
Golden Sands at Good Harbor: Across the street from the beach
Gloucester Cottage
- 7 bedrooms 7
- 3 bathrooms
- sleeps 12 12
- 3 nights min
- Ask about children
$1,780.00
from $1,780.00 / night
Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!
Gloucester Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 6 nights min
- Ask about children
$420.00
from $420.00 / night
Salt Island Views: Walking distance to Good Harbor & Long Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
$943.00
from $943.00 / night
Seaside House: Good Harbor Beach and the Back Shore right outside your door.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 6 nights min
- Child friendly
$1,023.00
from $1,023.00 / 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
- 3 nights min
- Child friendly
$1,649.00
from $1,649.00 / night
Annisquam Singing Pines: Private riverfront setting & tidal dock.
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- sleeps 10 10
- 3 nights min
- Child friendly
- Air conditioning
$1,361.00
from $1,361.00 / night
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Child friendly
$1,079.00
from $1,079.00 / night
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Gloucester Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 7 7
- 3 nights min
- Child friendly
$646.00
from $646.00 / night
Magnolia Tides: Multi-level waterfront home
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Child friendly
- Air conditioning
$1,391.00
from $1,391.00 / night
Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches
Gloucester House
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Child friendly
- Pet friendly
$519.00
from $519.00 / night
Long Beach House: Large, comfortable home just 285 feet from the white sands!
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- sleeps 10 10
- 6 nights min
- Child friendly
- Pet friendly
$729.00
from $729.00 / night
Sunset Cove: Waterfront home in Goose Cove section of Gloucester
Gloucester House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Air conditioning
$873.00
from $873.00 / night
Family Tides: Only a half-mile from Good Harbor Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Air conditioning
$1,015.00
from $1,015.00 / 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
$1,015.00
from $1,015.00 / night
Bell View: Private tennis court and an in-law suite.
Gloucester House
- 6 bedrooms 6
- 5 bathrooms
- sleeps 16 16
- 3 nights min
- Child friendly
$1,789.00
from $1,789.00 / night
Two Beaches: Walk to Long Beach or Good Harbor!
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- sleeps 8 8
- 6 nights min
- Child friendly
$687.00
from $687.00 / night
Squam Light: A newly renovated cottage, nestled in the village of Annisquam.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 9 9
- 3 nights min
- Ask about children
- Pet friendly
$687.00
from $687.00 / night
Helena House: European flair, close to Plum Cove Beach.
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- sleeps 7 7
- 3 nights min
- Child friendly
- Pet friendly
$591.00
from $591.00 / night
Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.
Gloucester Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Air conditioning
$512.00
from $512.00 / night
Ships Bell: Water views and amazing sunsets on a quiet street in Lanesville.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Air conditioning
$840.00
from $840.00 / night
Plaisance - Enjoy the best of Gloucester living.
Gloucester House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Air conditioning
$928.00
from $928.00 / night
Over By Good Harbor: Phenomenal views and just 0.2 miles to the beach.
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- 3 nights min
- Child friendly
- Air conditioning
$1,208.00
from $1,208.00 / night
Cedar Ledge Annisquam: Ocean views & traditional New England charm.
Gloucester House
- 6 bedrooms 6
- 2 bathrooms
- sleeps 14 14
- 3 nights min
- Child friendly
- Pet friendly
$1,468.00
from $1,468.00 / night
Terra Nova Cottage
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 6 nights min
- Child friendly
- Air conditioning
$697.00
from $697.00 / night
Chester Square: Waterfront home in historic Annisquam Village.
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Ask about children
$1,325.00
from $1,325.00 / night
The Mount: Walk to Niles Beach & Rocky Neck from this elegant home.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
- Air conditioning
- Pet friendly
$762.00
from $762.00 / night
Cottage at the Cove: A delightful vacation home close to Plum Cove Beach.
Gloucester House
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Ask about children
$508.00
from $508.00 / night
River's Edge: A charming 2BR riverfront home in Gloucester.
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- sleeps 4 4
- 31 nights min
- Ask about children
$276.00
from $276.00 / night
River Watch: Waterfront rental home with views and private dock.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
- Pet friendly
$600.00
from $600.00 / night
Sea Fox: Custom-designed home with rights to private Coffins Beach
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Ask about children
- Air conditioning
$1,022.00
from $1,022.00 / night
Bray Cottage: A charming cottage close to Wingaersheek Beach.
Gloucester Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Ask about children
- Pet friendly
$515.00
from $515.00 / night
Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
- Pet friendly
$710.00
from $710.00 / night
Your search has been expanded 5.7 miles to include more rentals
Directly on Long Beach Rockport MA
Rockport House - 3.1 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 14 14
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$679.00
from $679.00 / night
Ocean Front Cottage on Scenic Long Beach
Rockport Cottage - 3.1 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$516.00
from $516.00 / night
Booth Cottage: Walk down a private path to fabled Singing Beach.
Manchester-by-the-Sea House - 5.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 6 nights min
- Ask about children
- Pet friendly
$890.00
from $890.00 / night
Beautiful oceanfront home with sweeping water views and private beach.
Rockport House - 3.8 miles away
- 6 bedrooms 6
- 3 bathrooms
- sleeps 10 10
- 3 nights min
- Child friendly
$2,410.00
from $2,410.00 / night
Four Winds: A serene escape close to picturesque Rockport village.
Rockport House - 3.6 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Ask about children
$583.00
from $583.00 / night
The Lady Bug House
Rockport House - 4 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Ask about children
- Pet friendly
$581.00
from $581.00 / night
Historic meets contemporary at Pigeon Hill
Rockport House - 4.4 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Ask about children
$549.00
from $549.00 / night
The View: A classic New England cottage with panoramic ocean views.
Rockport House - 4.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
- Pet friendly
$588.00
from $588.00 / night
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