Gloucester 2-bedroom Apartments, Vacation Rentals & More - 53 Rentals Available.
53 Vacation rentals
Filters applied: 2+ Bedrooms
Boulevard Bungalow: Steps away from Gloucester's fabled Stacy Boulevard.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Air conditioning
$547.00
from $547.00 / night
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
$1,515.00
from $1,515.00 / night
Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!
Gloucester Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Ask about children
$339.00
from $339.00 / 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
$880.00
from $880.00 / 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
$866.00
from $866.00 / 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
$1,286.00
from $1,286.00 / 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
$1,213.00
from $1,213.00 / night
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Child friendly
$920.00
from $920.00 / 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
$534.00
from $534.00 / night
Magnolia Tides: Multi-level waterfront home
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- 3 nights min
- Child friendly
- Air conditioning
$1,610.00
from $1,610.00 / 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
$436.00
from $436.00 / 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
$687.00
from $687.00 / 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
$836.00
from $836.00 / 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
$730.00
from $730.00 / night
Bell View: Private tennis court and an in-law suite.
Gloucester House
- 6 bedrooms 6
- 5 bathrooms
- sleeps 16 16
- 7 nights min
- Child friendly
- Air conditioning
$1,369.00
from $1,369.00 / 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
$560.00
from $560.00 / 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
$613.00
from $613.00 / night
Kris' Kottage at Long Beach
Gloucester Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Ask about children
$579.00
from $579.00 / 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
$339.00
from $339.00 / 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
$410.00
from $410.00 / 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
$687.00
from $687.00 / night
Plaisance - a summer vacation rental near Bass Rocks
Gloucester House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Air conditioning
$723.00
from $723.00 / night
Rocky Neck Hilltop: Living is easy high atop Rocky Neck!
Gloucester Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Child friendly
$417.00
from $417.00 / 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
$1,010.00
from $1,010.00 / 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
$1,221.00
from $1,221.00 / night
Terra Nova Cottage
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Air conditioning
$617.00
from $617.00 / 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
$1,181.00
from $1,181.00 / 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
$418.00
from $418.00 / night
Cool Cove: Wingaersheek Beach plus your own private beach & all those views!
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Ask about children
$1,331.00
from $1,331.00 / night
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
$670.00
from $670.00 / night
Your search has been expanded 12.7 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
$593.00
from $593.00 / 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
$421.00
from $421.00 / night
Seacroft:Classic Victorian home with views of the ocean and twin light houses
Rockport House - 4 miles away
- 7 bedrooms 7
- 2 bathrooms
- sleeps 14 14
- 3 nights min
- Child friendly
$1,277.00
from $1,277.00 / night
Clamshell Landing: Bring your game to its squash & tennis courts!
Essex House - 5.3 miles away
- 6 bedrooms 6
- 5 bathrooms
- sleeps 14 14
- 3 nights min
- Ask about children
- Air conditioning
$2,067.00
from $2,067.00 / night
The Cable House: High-end oceanfront family home, 1/10 mi to Cape Hedge Beach
Rockport House - 3.6 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Ask about children
- Pet friendly
$1,101.00
from $1,101.00 / night
A sunny and charming 2-bedroom beach retreat close to Rockport's Front Beach.
Rockport House - 3.8 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Ask about children
$471.00
from $471.00 / night
Mill Brook Cottage: Enjoy New England charm in Rockport. Walk to the beach!
Rockport House - 3.6 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
$642.00
from $642.00 / night
The Rockporter: Enjoy beautiful views of Pigeon Cove Harbor.
Rockport House - 4.8 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Child friendly
- Pet friendly
$748.00
from $748.00 / night
Beach Bungalow: The perfect getaway to two of Rockport's finest beaches!
Rockport Cottage - 3.2 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Child friendly
$413.00
from $413.00 / night
Afternoon Delight: Toast the beauty of the river from the waterfront deck
Beverly House - 12.7 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Air conditioning
$616.00
from $616.00 / night
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